A year ago I was lucky enough to win the jackpot on the Euro millions Lottery. £32 million pounds and with no close family left, the entire amount ended up in bank balance. After buying a nice house, some flash cars and a 6 month around the world holiday, I was at a loss with what to do next.
At 40 years of age and little experience with women, I’d found myself surrounded by beautiful gold digging females, but I was very shy. To tell the truth, I’d never even had sex and being a 40 year old virgin, I was loathe to be the butt of a joke so I decided to pop my cherry with someone who wouldn’t make fun of me and decided to hire a professional.
I trolled the internet and picked a stunning dark haired woman named Rebecca. I spoke to her on the phone and explained that I had almost no experience and wanted to be taught the finer points of sex by a much more experienced lady. She seemed very nice and agreed to meet me at an exclusive hotel, telling me that she would make me into a total sexual dynamo and that I should leave everything to her.
The next day, I sat on the hotel bed waiting for her arrival with a sense of trepidation and almost called her to cancel our appointment. I was a virgin and would be making love to a beautiful woman for the very first time in moments. A knock at the door and my shaking legs propelled me up to answer. She was completely stunning and opened mouthed, I invited her inside.
“Hello Chris. It’s so very nice to meet you. I’m Rebecca, how do you do!”
I took her proffered hand and kissed it in response. She giggled and remarked that I was a proper gentleman, not like the usual riffraff she met. She was dressed in a smart business suit, grey pinstripe with a short skirt and a white silk blouse peeking out underneath. Her legs were encased in sheer black seemed silk stockings and on her feet were a pair of red patent leather 6’ stiletto heels. She pulled me over to the couch, sat me down next to her and took my hand in hers. I was breathless, sitting so close to such a gorgeous woman and when she put her hand on my thigh, my penis began to stir.
“First things first Chris, give me the £5000 we agreed for this evening and we can get on with the fun stuff.”
I handed her an envelope, stuffed with money and she counted it. She laughed, as she told me that she loved being paid for sex and that it made her pussy wet. She finished and pushed the envelope into a side pocket in the duffel bag she’d bought with her. She leaned across and kissed me, softly on the lips, slowly pushing her tongue into my mouth. I felt my cock stiffen in my boxer shorts, as we made out like a couple of young lovers before feeling her hand caress my genitals through my clothes.
“That’s a lovely hard-on you’ve got there, Chris and I’d love to see it! Let’s have you naked and I’ll see just what I’ve got to deal with!”
I stood in front of her and red-faced, stripped of my clothes, in front of a woman I’d just met. She was smiling as I finished and told me to sit next to her. She was very caring and I felt so turned on. My cock was dripping with pre-cum and she leant over and gently blew on my cock. I spurted uncontrollably and sprayed my spunk all over the floor. She laughed as asked her to please have pity.
“You expect pity, when you act like a total pervert in front of a lady! You told me that you’re a virgin, but I expected a certain amount of decorum! What do you think a beautiful woman would do, if you hadn’t paid her to have sex with you? She’d give you a telling off and make you apologise for such a dirty spurt! Right, I want you on your knees in front of me this minute and I expect a sincere apology!”
I sank to my knees and looked up at Rebecca, through wet eyes and in a trembling voice, apologised. She told me that I was a naughty boy and she would have to punish me for being so dirty. She pointed to her shoes and told me to lick them, to show her just how much I wanted to be beneath her. I begged her not to be so cruel, but she laughed and told me to lick like a good boy.
I bent down and with a small hesitation; I stuck my tongue out and licked her shiny red shoes. She remarked that I was I need of some very strict supervision, if I wanted to be taught to act correctly, in the presence of a lady. She asked me if I would like her to teach me to be a good boy and make me into something resembling a real man. I looked up at her and nodded, my ego shattered by this creature. She smiled down at me, patted me on the head and asked me to tell her all about my masturbatory moments.
I was hesitant and she told me not to worry, that she’d heard it all before. I lifted my mouth from her shoes and told her that I often wanked over some very naughty movies that I’d downloaded. She told me that I was just like every other man she knew, but that she thought that I was holding something back. She lifted my head up and kissed me hard on the lips, sucking my tongue into her, warm, wet mouth and I wilted. She bought my ear close to her lipsticked mouth and whispered in my ear that I needed to be totally frank with her. She licked my earlobe and I shuddered in a state of arousal.
In a whisper, I told her that I liked to watch strong women taking control of submissive men and making them do nasty, perverted things. She giggled and said that she thought I was a good boy, she asked me to tell her about my favourite website. In a quivering voice, I explained that I loved a site called Divine Bitches. She asked me what I liked about it and I said that Maitresse Madeline, who starred in most of the movies on the site, was a very controlling and dominant woman.
“I think you are a very kinky virgin, Chris and I need to teach you to be the submissive slave of a strong, dominant woman! Would you like me to make you into my slave, tonight? I’ll have you in my power and you’ll be nothing more than my property! How about if I make you my slave? Would you submit to my every desire and instruction or should I just take your money and leave?”
I looked at her and nodded, my cock throbbing. She told me in a very clear voice, to tell her that I wanted to be her slave and I stared at her with desire. I looked at her and in a very loud clear voice begged her to make me her slave. She told me that I would have to prove to her that I really meant it. I was on my knees, naked, in front of a prostitute that I’d paid for sex and she wanted me to prove that I deserved to be her slave.
I promised her that I would do anything she wanted, but would she please allow me the honour of serving her in any way she deemed. She took my hand, pulled me up onto the sofa and gently wrapped her hand around my cock. She squeezed, slowly and with a deliberate force, asking me if I deserved to be the plaything of a beautiful woman, because I was clearly such a loser. I sobbed and told her that I was in need of a very strict seeing too. She smiled and kissed me on the forehead, like a Mother would a small c***d.
“I’ll only do it if you’re willing to promise that you won’t spurt again tonight! In fact I want you locked away in a chastity device, so that you have no chance and I don’t have to look at this useless cock ever again! You’ve no need to be hard in front of me and I expect you to be under my control! Understand that I want your orgasm’s to be mine, from now on, mine to own and control! I’ll have the key and the only time I’ll release from my imprisonment, is when you pay me to spend time with you! No more spurting outside of my presence!”
I looked at her and with a shudder asked her if she would please, take away my hard on’s. She giggled and told me that I was such a sad bastard, but because I’d asked so sweetly, that she’d love to. I told her that I needed to be under her control and she obviously was the 1 to make me her slave. She reached into her bag and rummaged around before pulling out a clear plastic chastity device. She passed it to me and asked me if I was sure. I was so humiliated, as I explained that I wanted her to lock me away, that I sobbed like a c***d, caught with his hand in the cookie jar.
She slowly masturbated me, as I begged her to be my keyholder and make me into a chastity slave. She kissed me hard, on the lips and licked my lips before reaching down, taking my chastity device into her hands and unlocking the small metal padlock. She slowly placed the prison around my semi-hard genitals and fastened my flesh into her plastic prison. She sighed and asked me to stand in front of her.
She placed her hands on my hips, bent forward and took my plastic covered cock into her warm wet mouth. She sucked on my cock, like the whore she was and made me shudder in desire. I was receiving my first blowjob, but I was unable to enjoy the experience properly, barely even feeling anything more than a sensation of warmth. She pulled her mouth away, a large strand of drool connecting her mouth to my chastity device and slurped it up. She told me that I was a complete and total moron, but that she would make me insane with want.
“You paid me to pop your cherry tonight and now you’ve got no chance of sex with me! I hope you enjoyed that spurt earlier as I intend to make you suffer for anymore opportunity’s’ to milk in my presence! You should be prepared to be without any hope of release tonight and for the rest of the week! From now on, I’ll be expecting you to pay me triple for my time, slave and you’ll be glad of it won’t you?”
I thanked her for her willingness to be my Mistress and begged her for a favour. She nodded and I asked her to spank me. She asked me why I deserved a spanking and I told her that I was a very naughty boy and was in need of immediate correction. She was without pity, as she pulled me over her clothed lap, pushed my head down and told me that I was correct. I would be spanked for my perverted behaviour in front of a woman and she would enjoy my discipline.
She pushed my lips against her stocking covered leg and told me to kiss her silk stockings. As my lips touched her legs, her hand connected with my bottom and I shuddered at her punishment, for the next 5 minutes, as I took a very hard, bare bottomed spanking. I kissed my mistresses stockings and wished that I could lick her shoes. Afterwards, I was unceremoniously pushed to the floor and told to suck on her stiletto heels. Through tear filled eyes, I looked up at Rebecca, as she forced those long thin heels, down my throat and I licked every inch.
“Good boy, Chris, suck on my stiletto heels and show me how much you need me to own you! You’ve been in need of a strong woman to show you for some time that you need to be under supervision and I’m more than willing! I’m a prostitute, a whore and a slut, but I’m superior to you in every way, aren’t I? I bet you’d love to be my sissy wouldn’t you? I think a nasty little slut like you would be perfect in a pair of frilly knickers and stockings, with lots of make-up on your face! I want you dressed in some lingerie right now and don’t pretend you aren’t in need of my silk and lace! I know just what you deserve, Chris and I’m going to humiliate you, utterly!”
She pulled a pair of pink silk and frilly white lace knickers, from her bag and passed them to my open hands. They were completely feminine, but I couldn’t imagine any woman wearing such a girly pair of knickers, ever. I asked her if they were hers and she told me that she would never be caught dead in such sissy knickers, but that they would look perfect on me. I was entranced by the silky confection and when she told me that I was to wear them for her, I begged her not to be so imposing, but she was in no mood to be put off by my indecision.
She reminded me that I had begged her to take control of me and she intended to humiliate me completely, like a sissy and I should be very worried. She asked me if I liked the pretty knickers and I shrugged. She pointed out the word stitched on to the front of the panties, in darker pink letters. She asked me what it said. I read it out to her and she laughed at my hesitation.
“It say’s SISSY, doesn’t, Chris? You’re going to wear a pair of very frilly knickers, with the word sissy on the front and I’m going to love it! Fancy a grown man wearing frilly girl’s knickers! I reckon you’ll be in heaven won’t you? Don’t try and pretend that you’re a strong man to me; after all, I just made you cry like a little girl when I spanked your soft bottom! Now hand them back and I’ll help you put on a pair of naughty sissy knickers! That’s it step in, 1 foot at a time and I’ll pull them up your legs, settle them around your waist, like a princess!”
With a sense of theatre, Rebecca, drew those knickers up my legs and smoothed them onto my bottom. She turned me around, fussed with the frills on the behind and took me by the hand. She led me, very deliberately, into the bedroom and stood me in front of the floor length mirror. I looked ridiculous. She was fully clothed, her suit pristine and her face glowing, while I was dressed like a fairy. I had a tear streaked face, an embarrassed expression and a very frilly pair of little girl’s knickers on.
She reached inside and very lightly, tickled my balls, as she looked into my eyes and pretended that everything was completely normal. I was in submissive heaven, but she made me even more ashamed when she told me that I was clearly a sissy and I should be happy that she’d shown me the truth. I begged her not to call me that, but she was adamant. I was her sissy and I would be required to wear lingerie at all times from now on. Whimpering, I asked her if she was joking, but she looked at me with scorn and reaching around to the rear of my knickers, showed me the frills in the mirror.
“Look at your bottom, Chris, it’s so girly in your knickers and I think you should be honest with me, don’t you? Tell me that you’re a sissy and want to dress in lingerie, for me, like a good girl! Go on and I’ll let you look up my skirt at my panties! Don’t be shy, just us girls here and I won’t tell a soul about your kinky fetish! You do want to be my little sissy, don’t you, Chris? You do want to be dressed in the most frilly of lingerie and dresses, dripping with lace and made from the softest of material’s, don’t you? I’ll watch, as I unlock your chastity and let you masturbate in your sissy panties! I’d love to see you milk in a pair of knickers, as I look down at you and laugh as you humiliate yourself for my amusement! You want to please me don’t you? Well, what are you hesitating for, tell me that you’re a sissy!”
With a shudder and a squeak, I told Rebecca, that I was a sissy and could I please dress in some girly lingerie. She told me that I would need to buy some clothes for our next meeting. She asked if I had a laptop with me and when I told her I did, she had me turn it on, connect to the internet and bring up a site called Birch Place shop.
We sat at the table, very close together, her soft well-manicured hand inside my sissy knickers and told me to scroll through the site. I was open mouthed as I was directed to order item after item. The most feminine of clothing, in the most silky and frilly designs, but I would be the 1 wearing them. I was to be feminised, for Rebecca’s pleasure and I was quite horrified. She asked me what the matter was and I told her that I was scared that people would find out about what she demanded that I do for her.
“You needn’t be worried, Chris, I wouldn’t want you to be humiliated in front of your friends and family for being a sissy! No, you’ll be humiliated because you’ll be dressed like a little girl for me! You pretended that you wanted to have sex with me when you paid for my services, but the truth is you needed me to lock away your pathetic cock and turn you into a sissy! Don’t worry; I’ll give you everything you deserve and more! I’ll turn you into a simpering French Maid and you can bath, dress and serve me in the most intimate of ways! Imagine me, naked, dripping wet and you’re drying me with a towel! You’re on your stocking covered knees, petticoat peeking out and knickers on display, but I’ll be so nice to you, I’ll let you dress me in my lingerie and help me into my clothes! Won’t that be satisfying, no spurts but you’ll have the pleasure of dressing me for my appointments! Yes sissy, I’ll be fucking real men for money, while you stay home, being my Maid and you’ll love it, won’t you?”
She nibbled on my ear and rubbed my balls, telling me that she loved to be filled by big thick cocks. She was relentless, as I was made to listen to her descriptions of her daily life, but she let me know that I could only look forward to serving her as a sissy. She asked me if I would be her toilet cleaner and make sure that her throne was kept perfectly clean for her bottom. Open mouthed, I told her that I didn’t want to be a toilet slave, but she told me that I should be privileged to be allowed to touch her toilet.
She explained that only a very lucky sissy deserved the position of toilet slave to a woman of her beauty and profession. She was clearly very earnest, as I was told that I would have to spend at least 3 hours a day, cleaning her porcelain, with my mouth and tongue. Her hand was making me writhe, as she slowly tickled my red bottom and used her middle finger to caress my hole. As I protested this latest violation, she put her other index finger to my lips and shushed me.
“Chris, I hope you realise that I’m only doing what’s best for you? You won’t have to pretend to be anything other than a frilly sissy with me and when you clean my toilet, making it shine for my bottom, I’ll be ever so grateful! I’ll make sure to tell you all about the men that I fuck while I’m working and I’ll even save my dirty panties for you, as well! They’ll be full of my pussy juice and my clients spunk, dripping wet and ready for you to hand wash! Fancy scrubbing the spunk filled panties of your mistress, whilst dressed as a sissy French Maid and afterwards, as a special treat you can clean my toilet! If you make it shine, I’ll fuck you, just like you always wanted to, Chris! I’ll fuck you so hard you’ll fill your sissy knickers with spunk, as I push my strap-on in and out of your bottom, just like a real little girl!”
She was making me feel so dirty, as I was told that I would be sodimized by her, just like her finger had started to do and I begged her not to stop. She smiled and told me that I must be a sissy, as only real sissy’s liked to have their bum’s filled. She pulled her hand away from my hole and asked me if I would like to be her French Maid. She told me that she’d carry on with my fingering, only if I was a good girl and told her that I’d be her French Maid. Sobbing with shame and pent up sexual frustration, from her teasing and my desire for her, I told her that I’d be honoured to be her French Maid.
She had me click on the Maids costumes icon, on the website and asked me to pick out the dress for my service to her. As I scrolled down the page, she began to tease my bottom again, making me shudder and shake. She pointed out 1 dress, called the Fanny Sissy dress and told me that I would look so cute in it. I clicked on the page and was flabbergasted at the dress, as well as all the accessories. She had me order the dress, in baby pink, with lacy white petticoats and matching lingerie. She then had me order a pair of 6” Steffie pink stiletto heels. I told that I wouldn’t be able to walk in such high heels, but she seemed unimpressed with my negativity and slapped me, hard across my face.
“You’ll so get the hang of such high stiletto heels, Chris and you’ll look so good tottering around, obey my commands, your bottom wiggling in your frilly Maids knickers and I’ll be able to see them quite clearly! Look how short that dress is and how high your petticoat lifts it! You’ll be on display, but your cock will be safely locked away in your chastity device and I don’t expect you’ll be spurting till you’ve proved how good a Maid you are! Maybe if you please me and show me that I’m the centre of your universe, I’ll release you! How about if you promise to really humiliate yourself for me, I’ll even let you use a pair of my dirty panties to spurt in! Every drop, inside my panties and you can keep them! Only if I can totally humiliate you though, I mean making you into a figure of scorn for all women and it would have to be public!”
She was making me into a complete sissy and I couldn’t seem to say no to her. In fact I would have been willing to do anything for her at that moment, as her finger sank, knuckle deep, into my bottom and slowly massaged my aching hole. She was smiling at me, as I was frigged like a cheap slut and I begged her not to stop. She asked me if I liked her playing with my sissy pussy and I nodded yes. With an almost sadistic push she touched my prostate and I began to leak in my knickers.
I was in heaven, but just as I felt like I was about to spurt she pulled back and began to tease my puckered hole. I begged her for a spurt, but she told me that I was not worthy of a girly milking inside my pretty knickers. She told me that only really nasty sissy’s got to spurt in there silk knickers and I wasn’t nasty enough. I tried to reach inside my soft silk prison, but she slapped me, once and then twice, hard across my face. She was very cross and she made fun of me.
“What a naughty sissy you are, Chris! Fancy trying to play with your cock like a boy, when you’re clearly nothing more than a girly sissy! Don’t expect your crocodile tears to work on me, I know just what you deserve and touching yourself is not allowed! You need some real chastisement and I’m going to make you cry just like the little girl you are! Wait right there, Chris, it’s time for you to be caned! Quiet you fairy and I’ll just get my stiff springy cane!”
She stood up, left the room and returned a minute later with several items. The first was a thin whippy cane, perhaps 4’ long and very bendy. She also had a pack of white lacy topped nylon hold up stockings. The final items were a pair of black patent leather Mary Jane’s, adult sized and obviously meant for me. It took her only a couple of minutes, to have me wearing those stockings and shoes before she bent me over the back of a chair. She pulled my knickers down, they collected around my spread knees and she asked me if I was ready for a well-deserved caning.
I begged her not to cane me, but she sneered and told me that I was acting like a real girly. She said that I should feel free to cry and squirm as much as I liked, but that I shouldn’t stand up or she’d start my punishment from the beginning and double the amount. She stood beside me, her cane in her right hand and used her left hand to caress my still red bottom, from my earlier spanking. She sighed and explained that a sissy’s bottom should be kept in a state of deep blushing rose. She was delighted that I would learn this lesson so soon in my training.
“Now then let’s be having you, sissy! A nice juicy dozen for my pretty little sissy girl! Do you like your shoes, Chris? They make you seem much younger; maybe a 3 year old girl, being punished by her Mommy for being rude and you’d be right! I’m going to dress you as my little 3 year old sissy girl, parade you to all your friends and then I’m going to give you a hard spanking! All your friends will see you crying and blubbering, dressed as a sissy and they’ll call you horrible names! Fairy! Sissy! Pantywaist! Faggot! They’ll be on the money though won’t they? You do want me to be your Mommy and humiliate you, don’t you? You don’t, well let’s see what you say after your caning!”
Rebecca bought down her cane, striking my right cheek and I howled in pain. Her spanking earlier was a walk in the park compared to this beating and I was soon crying. She cooed and told me that Mommy was very proud, but that I should beg her to dress me as her little sissy girl. I looked back over my shoulder and she grinned at me, but I told her that I wouldn’t be humiliated like that. She just winked and said that I’d regret being so silly.
The next stroke was even harder and crossed the first. I wailed, but she just used my pain as encouragement, as she struck again. She reached down and touched my throbbing bottom telling me that Mommy only wanted to make it better, but if I didn’t admit to her that I was her little sissy girl, she’d have no choice, but to keep striking me. I looked back and with wide tear filled eyes, watched as she reached under her skirt and pushed her fingers inside her panties. I heard a soft squelching sound and drooled as Rebecca masturbated.
“I’m so wet at the thought of you dressed like a little girl, Chris and I need to have a little wank! You see Mommy’s like to frig there hot wet pussy’s when they humiliate there little sissy girl’s! I bet you’d be able to watch as I played with myself, kneeling at a respectful distance and hands tied behind your back! Would you like to see Mommy masturbate, Chris? You would, well then you must want to dress as a little girl! Don’t worry about everyone finding out that you’re a sissy, I’m sure they already know, after all I could tell from the moment we met and I soon had you in frilly knickers! Go on say yes and I’ll finish off your punishment and we’ll pick out some nice dresses for you online!”
I couldn’t help nodding, as I was mesmerised by the sight behind me, but as soon as she saw my surrender she pulled her fingers out and continued my caning. By the final stoke I was a blubbering wreck, so when Rebecca lifted me up, pulled up my knickers and sat me on her lap, I was under no illusion about who was in charge. She gave me a big hug and stroked my hair, telling me that I was Mommy’s precious little sissy girl. She made me feel like the centre of her world and I had never felt so close to another person.
She pointed to the laptop and told me to click on the adult baby page. I was to be emasculated by this young beautiful woman and I tried to object, but she pushed her fingers deep in to my mouth. The fingers she’d used to masturbate and she goggled, telling me that I should suck on her fingers until my pacifier arrived. She kissed me on the forehead telling me that I was good at using my mouth and she would be looking forward to watching me suck on 1 of her nice big strap-on cocks. I licked and sucked, my eyes wide and tear-filled, but she soon had me choosing my latest collection of dresses and lingerie.
“With your French Maid’s dress and lingerie, you could almost pretend you were a real man under the outfit, but no such luck with these ensemble’s, sissy! There perfect to let everyone into your secret, aren’t they? Don’t worry though I’ll be a little bit respectful of your boundaries, I won’t put you in diapers and have you use them in front of our guests! See I’m such a caring Mommy aren’t I? After all a 3 year old girl doesn’t use diapers, they use a potty like a big girl! Just ask me for permission to go wee-wee or p*o-p*o and you can fill your potty like a good little sissy! Oh, are you all right Chris, you keep crying, maybe you’ll feel better knowing we’ll all be there to make sure you fill your potty and then I’ll wipe your bottom! There’s no privacy for little girl’s using their potty’s and you’ll be Mommy’s good girl and enjoy your observation, won’t you?”
I almost spurted in my knickers. I was so humiliated and strung out, though, I couldn’t tell if I was almost wetting myself or spurting. Rebecca was once again fingering my hole as I picked numerous dresses and lingerie from the website, along with assorted accessories. When I added up the total, it came to over £6000. I asked for my wallet, pulled out my credit card and paid. Rebecca giggled and told me that she’d had enough for now and she was leaving. I begged her to stay, but she told me to stop being so clingy.
She stripped me naked, tidied up her appearance and said goodbye. She reminded me to call her to set up the next session and told me that I should bring much more money for her next time. She also told me that I should bring my French Maids uniform, all associated lingerie, stiletto heels and nothing else.
“I must say I’m rather looking forward to our next encounter, Chris! Not because you’ll be there, but I can’t wait to take lots of your money and then humiliate you! Next Friday, call me at 11 o’clock and we’ll confirm your arrival for 1 o’clock. Oh and sissy, if you think you can just forget all about me and never contact me again, you should be aware that I recorded this entire session! Don’t think for a minute that I won’t spread it all over the web if you don’t obey my orders!”
With that she stormed out of the room. I stood there, naked apart from my chastity, remembering that she had the key and wishing that it was next Friday already.
I spent the following week, holed up at home, in a complete state of panic. I was so ashamed of my session with Rebecca and yet I’d never felt so horny and turned on in my entire life. The fact I was unable to masturbate, because of my chastity device, made the week last even longer, but when the packages containing my sissy wardrobe arrived I almost used a hacksaw to remove the plastic contraption and wank. I persevered, though and made it all the way to Friday morning. I reached for my phone and called Rebecca, my heart pounding and my palms sweating.
She answered after the 6th ring and immediately tore into me. She asked me if I was her little sissy girl, telling me to answer her in a high lisping voice and make it quick. I told her that I was her little sissy girl and begged her to allow me to serve her today. She reminded me that I would be her French Maid and that I was to arrive promptly at 1 o’clock. I told her that I would be on time and that I was in need of a well needed spanking.
“Don’t worry, I’ll soon have your pert little bottom a lovely shade of red, but you must do something for before you arrive. I want you to go to your nearest chemist’s, ask a member of staff for hair removal crème and return home to use the contents! The only hair I expect on your body when you walk through my doors, are your eyebrows and the hair on top of your head! Am I making myself clear, sissy? I want you as smooth as a little girl for your Mommy! Now get to it sissy!”
As soon as she put down the phone I was out of the door, in my car and on the way to the chemist. 2 hours and some stretching to some very hard to reach places later, I was pulling on to Rebecca’s drive and lifting out clothing bags before knocking on her front door. She opened it, looked at me with amusement and beckoned me inside. She had me put down my bags, strip naked and then lock away my male clothes in a large cupboard, in the hallway.
Rebecca stood in front of me, dressed in a light summer dress, very short, with shiny white nylon tights and 3” heels. She pointed to the floor in front of her and I knelt down. She took a few moments to inspect my hairless body, tutting occasionally before pointing to her shoes. I bent over and licked them. She meanwhile took something from a shelf and clipped it to my chastity device. It was a leash.
“Come along now, sissy! It’s time for your servitude to begin and I want you to meet a dear friend of mine, Gemma! Now don’t be silly, you’ve got nothing to be scared of, I’ve let Gemma see the nice movie from our last meeting and she’d agreed to watch you this evening, while I’m out with my client! Come on, this way and we’ll just let Gemma say hello!”
I was tugged along, behind my smirking mistress and led in to a large, spacious living room. Sat on a leather sofa was a young red haired woman, dressed in a form-fitting red dress, with black fishnet stockings on her legs and a massive pair of red stiletto heels on her feet. She was stern faced and looked at me with a haughty expression. I was already scared, so when I was led over to her and ordered to kneel at her feet, I almost fainted with shame. I was naked, in front of 2 fully clothed women, except for my chastity and let me tell you I was grateful for the plastic.
Rebecca introduced me to her friend and handed my leash over to her. She said good-bye to Gemma and I realised that I was to be left alone with this unknown woman while my mistress headed out. I was horrified at the thought, but Rebecca giggled at my shocked face and told me to listen carefully to Gemma. She was to be obeyed in every way or she’d be informed upon her return and I would be caned once again.
“Don’t worry, Chris, Gemma will supervise your feminisation, while I head into town to buy some slutty lingerie for tonight’s client! Don’t forget, that it’s your job to prepare me for tonight’s work, so I couldn’t really help you dress or the whole point would be lost! Now be a good girl for Auntie Gemma and Mommy will let you suck on her stiletto heels when she gets home! You can show Gemma how well you use your mouth! He’s like an industrial vacuum, Gemma, he’s a born cocksucker and I can’t wait to fuck his mouth with a massive strap-on!”
With that she headed out of the living room in a haze of sexy perfume and I heard the front door slam. The sound of an engine followed quickly and I was truly alone with this stranger. She tilted my head up and prised open my mouth. She spat a large amount of her saliva inside and closed my mouth. She grinned at me before slapping me hard across my face. She pointed to her shoes and I leant down, my ears ringing and face throbbing and began to lick her shoes.
She held my leash in one hand and used it to direct my pace, making cover every millimetre before she seemed satisfied. She pushed me back, stood up and led me back out to the hallway. She pointed at my clothes bags, her silence like a dagger in my heart and she motioned me to pick them up. I was led through the kitchen and up a back flight of stairs, up into the loft area. Inside was a small bedroom, laid out with a single bed, covered in pink lacy sheets, a pink dressing table, with a large mirror and a small stool in front of it.
The dressing table was covered with make-up, perfumes, and dozens of different beauty implements and on a mannequins head, a long blonde wig. I was pulled over to the bed and Gemma indicated that I should put my load on the pink sheets. I did and she bought me over to the dressing table, sat me down and using the leash, tied me to the chair. She reached in to 1 of the draws, pulled out a ball gag and fastened it around my head. I was unable to make more than a moan, as I drooled over the pink latex gag. I was turned to face the mirror, as Gemma headed over to the bed.
She began opening the bags, emptying the contents and hanging the dresses in a large pink wardrobe. The lingerie and stockings, she put into a chest of drawers, also coloured pink and tidied up a bit. Every time Gemma lent over to pick up something from the bed, I got an eyeful up her short dress and ogled her pantie covered pussy. She was wearing a tiny black silk g-string; it was buried deep between her buttocks and was in a real state. My chastity was doing its work well, but I was dribbling, my full balls leaking from the excitement and I spent a little too long looking and Gemma noticed. She seemed prepared for my display, but she looked at me with pity.
“Peeking up my skirt, sissy, well you’re for it now and look at that tiny piece of meat between your legs! It’s sprung a leak, but I’m sure you need some kind of release don’t you, Chris? What if I put on a little show for you did a little striptease and let you out of your cage? Would you like that, girly? Would you like to spurt in front of me, as I took off my clothes and called you naughty names? You would, well you’ve got no chance! I’m going to dress you in some very cute lingerie, a frilly sissy Maids dress and put on some very slutty make-up, so the only hope you’ll have of spurting today is when you bathe and dress Rebecca! You’ll be dressed like a total sissy, while she’ll be completely naked and you won’t have any hope of release at all! Now let’s make you all pretty for your Mommy’s big day!”
She released me from my chair, untied my leash, but left my gag in, telling me that I didn’t to speak. She took my hand, led me into a small bathroom and told me to run a bubble bath. She poured in a massive amount of flowery smelling bath salts and told me to get a move on. She peered back around the door and asked if I’d noticed what was different about my sissy bathroom. I looked perplexed, until I sat in the hot bath and looked across the room. There was no toilet. I thought this strange until Gemma re-entered with what I could only describe as a big opaque pink plastic potty. In large dark pink letters on the front were the words “STILL POTTY TRAINING”!
“Look what Rebecca’s bought for you Chris, your very own potty and I think it’s just perfect for a naughty little sissy girl like you! Whenever you’re under our control the adult toilet is off limits and you will use this darling potty! Just present yourself to 1 of us, curtsey like a good girl and wait for permission to speak, when indicated you should ask to use your potty, making sure to use a nice high lisping sissy voice and explain if you want to go wee-wee or p*o-p*o! If we think you’ve been a good and obedient sissy, we’ll get your potty and you can use it wherever you find us! Maybe we’ll be outside or with company, but don’t worry your pretty little head, 1 of us will hold your hand and lift your frilly dress and petticoats out of the way so we can see! Don’t cry, sissy, I bet you’ll soon love using the potty and if you don’t and have a nasty accident, your Mommy will put you into some lovely soft diapers and you can wee-wee and p*o-p*o to your heart’s content!”
Gemma was openly laughing at my mortified expression as she confirmed what Rebecca had threatened at our first meeting; I was to be potty trained like a little girl. I heard Gemma laughing in the other room and she shouted that I better hurry up or she’d put me in diapers, under my French Maids uniform and could explain to my Mommy why I was dressed like a total pervert. I stood up stepped out of the bath and quickly dried myself before entering my room with the towel wrapped around my body.
Gemma took 1 look and ripped it from my body, pushed me over to my dressing table and instructed me in my body moisturising. Next were some feminine deodorant and a very strong rose smelling perfume, which she sprayed all over me. Gemma took my hand and led me over to the bed where my lingerie was placed. I was handed a pink satin and white lace garter belt, trimmed with pink glass silk and small pink rose above the centre. I was instructed to attach the garter at the front before turning it around. I looked in the mirror and my chastity covered cock was framed by the girly garter belt.
Gemma pushed me down onto the bed and handed me a packet of sheer white silk stockings. I very gently removed the delicate hosiery and I was shown how to put on my second pair of stockings. I attached the garter tabs and I felt a smack to the backs of thighs. Gemma hissed at me to straighten my seams or she’d spank my naughty bottom. Using the mirror I fiddled the sheer stockings until I had perfectly straight seams.
“That’s much better, sissy! We both expect you to look perfect, as you show us your devotion by the wearing of lingerie and dresses, instead of being a real man and fucking us with that cock! Fancy letting Rebecca lock away your manhood, especially when you’d paid her to fuck you! Is it true you’re still a virgin? You are, well don’t expect to pop your cherry anytime soon, in fact you better get used to being very frustrated, your balls full and cock dripping in your pretty little girl knickers! You love it don’t you? The more we tease and humiliate you, the more you want! The first time you use your potty, I’m going to masturbate right in front of your face and you’ll have a great view as I orgasm and laugh at you, pervert! Rebecca was right, you’re a total sissy!”
I felt about 3’ tall as she checked my stockings 1 final time before she helped me in to my knickers. She knelt in front of me and I stepped in to made of the same materials as the garter belt, it dripped with bows and frills. Gemma pulled it over my waist and settled my knickers in place. She whispered in my ear that I looked delicious. She turned me around bent me over and had me check out the ruffle covered bottom. She wondered if my dress would cover up my pretty knickers, but told me that I’d have to give her a look up her dress before my Mommy. I looked at her, questionably in the eye and she told me that Aunties need to check that there nasty little sissy Nieces haven’t filled their pretty knickers with spunk before Mommy sees.
Next was a pretty pink training bra, stuffed with dirty panties and made of pink lace. Just like my garter belt I tied it at the front, turned it round and put my arms through the straps. Auntie Gemma asked me if I liked her dirty panties and red faced I nodded. She laughed and told me that she’d bought a black bag full of her dirty lingerie with her. I would spend the time Mommy was fucking her trick later hand washing every piece. She rubbed my bottom through my knickers and asked me if I would like to be her permanent lingerie cleaner. I nodded and she just smiled.
“Bit of silly question really, I mean a chastity wearing sissy needs to touch and play with as much frilly, silky lingerie as possible! Here you go, Chris run your hands on your lingerie, feel how soft it is, how frilly it is and it’s so much more satisfying than playing with your cock, isn’t it? You can tell your Auntie the truth, I won’t tell anyone! You’ve been dreaming about this all week, dreaming about serving your Mommy, bathing her, dressing her and watching her go off and fuck a real man! That’s the truth, your Mommy is a whore who suck’s and fuck’s cocks for a living! She takes it in every hole and gets paid for it! She loves it, sissy, love’s all cocks, but yours! She just wants to lock it away and cover it in silk, but I know that you’d love to fuck your Mommy, wouldn’t you? Tell Auntie, right now!”
I nodded and she smiled at me. She laughed and said that I was a complete loser. She pointed at my dress and told me that it was time. The body was made of pink glass silk and edged in masses of frilly lace. She held it low down and holding on to her shoulder for balance, I stepped inside a silk and lace prison. Auntie Gemma pulled up my French Maids dress, positioned it around my waist and fed my arms through the huge puff ball sleeves. She buttoned the dress at the back and showed me a small padlock, which she used to lock me into my dress. She tied off a massive bow made of frilly lace and ribbon. It held the large white silk lace pinafore in place.
She fussed with my dress for a few moments before she turned me around and asked me if I’d like my Auntie to petticoat me. Grinning at my hesitation she told me that this was it, no going back, a sissy’s first petticoat made sure that he’d never be normal again and did I understand. I looked down at the floor, utterly ashamed at myself as I nodded and sealed my fate. She picked up the very short petticoat and once again knelt in front of me. I stepped in to that mass of frills and lace. In moments I was petticoated and I felt utterly sissy.
“There’s nowhere to hide now, honey! Everyone can see that you’re a petticoated sissy! Come here sissy and Auntie Gemma will give you a nice big hug! Wow, your dress is so soft and silky! Do you like wearing a frilly petticoat for Mommy and Auntie? You do, well aren’t you a good girl and don’t forget that we know that you deserve to be feminized! A real man would have fucked your Mommy and treated her like a whore, but you wanted to show us just how much you need this! Let’s just check out your knickers, I love the ruffles and Mommy will to!”
Auntie Gemma sat me down on my bed, passed me my 6” pink stiletto heels and told me to put them on. I slipped on my new shoes and signalled her if I could please have her help to stand. She told me to wait, that something was missing from my shoes. She knelt down, attached a pair of small padlocks to my shoes and told me that I looked better. She explained that doing housework in such high heels would make my feet hurt, but to prevent me from getting relief, I was too locked in my stiletto’s. She stood in front of me and helped me to my feet. I almost fell over and she said I looked like a new born swan trying to balance on a frozen pond.
She took my hand in hers and helped me find my centre of balance, allowing me to strut across the floor like a real woman. Auntie Gemma told me to bend over, keeping my ankles crossed and bending at the waist. She called this the sissy bend and I was make sure that I showed everyone, just what I was wearing under my dress. She then showed me how to curtsey for a ladies attention and acknowledgment. I practiced over and over again, holding my dress and petticoat in either hand, making a spectacle of myself. Gemma spanked the backs of my thighs, just above my stocking tops, every time I failed and soon had a bright red shine on the backs of my legs.
“You look so submissive and girly doing that, so make sure that I see a proper job from now on! You should curtsey when entering the presence of a lady or when 1 enters your presence. The only time you should curtsey otherwise, is when you are ordered to complete a task and you need to show you understand our demands! You see, we have no desire to hear the prattling on of such a naughty little girl so open wide for your diddum’s, sissy!”
Auntie Gemma unstrapped my ball gag, used a baby wipe to clean the drool from my face and opened a draw. She bought a large, pink latex pacifier up to my face and pushed it into my open mouth. With a flourish, she tied a large ribbon around my neck and made a big floppy bow. She asked if I liked my pacifier. I simpered at her question, but she wouldn’t relent. She reached under my dress and ran her hand over my stocking tops and across my garter tabs, making me totter on my stilettos.
She stood very close to me, so close that I could smell her perfume and the aroma of her warm body. She teased my bottom, reaching inside my knickers and cupping my chastity, I was so horny and Auntie saw my desire in my eyes. She kissed my neck, gently and across my shoulders, treating me like a virgin being deflowered by her lover. She asked me if I wanted to be a good girl and I nodded, imploring her with my body. She laughed and told me that I was a real slut.
“You’re pathetic, aren’t you? Fancy getting all squiffy when I put my hand inside your knickers and give you a little tickle! I bet you’d love it if I pushed my finger up your bum and frigged your hole, but I won’t until you tell me you love sucking on your pacifier like a good little sissy girl! You do love your pacifier, well no need for a finger in your bottom then, just suck and imagine it’s a big dildo, strapped around my waist and ready for you! Show me you’re sucking skills, sissy!”
I sucked like a man possessed and I suppose I was, I was obsessed with this young woman how made me feel like a dirty little slut. She giggled and asked me if I would like some make-up on my face. I was gone at this point and I just acquiesced. I was sat down and given a crash course in the use of blusher, eye shadow, lipstick and all the other products women use to enhance themselves. She turned me to face the mirror and gasped. She’d made me look like a cross between a porn star and little girl. She’d given me bright pink lips, smoky eyes, but it was the freckles that made me look like a little girl.
She pointed to the blonde wig and using hair pins, attached it to my head and gave me instant long hair. She pulled the hair into large floppy bunches, reaching down the side of my head and across my white bare shoulders. Taking a pair of pink ribbons she fastened the ends of my new hair into a very girly hairstyle. Auntie lifted me to my feet and giggled at my appearance. She called me a very naughty little sissy and asked me if I knew what I needed to finish off my ensemble. I shook my head and she laughed.
“You need some very sexy perfume, Chris! No sissy is ever finished dressing until his knickers are drenched in perfume and your knickers need some right this minute! I think something very flowery, perhaps like the roses you used in your bubble bath earlier! Now lift up the front of your dress so that Auntie can perfume your knickers! Very good, sissy, but let’s make sure there completely covered, shell we! Bend over and I’ll spray your bottom!”
Auntie Gemma perfumed my knickers and I looked at her with utter devotion as she made me into her version of a simpering French sissy Maid. She bent down and sniffed my bottom, laughing that I had a very lovely smelling pair of knickers on and did I want to thank her. I curtseyed and she laughed as knelt down in front of her and licked her shoes in devotion. She allowed me to abase myself for a few moments before I was told to follow her.
I was barely able to keep up with her, as I tottered on my 6” heels and I was soon far behind her. I saw her enter an upstairs room. I knocked on the closed door and waited for her to invite me in. She told me to enter and I stepped into a well-appointed bedroom. I curtsied and waited for instruction. Auntie Gemma looked at me like a lion looks at a goat. She was the predator and I was her prey. She pointed to the floor next to her bed and asked me if I wanted to look at her dirty lingerie. I curtsied again and sank to the floor next to her.
“You’ve been a good girl and you deserve a treat, so I want to watch you play with my dirty panties and soiled stockings! Be a good sissy and look under the bed for a bag. That’s the 1, pass it here and I’ll show you my lingerie! Such a lucky sissy, not many sissies get to play with Auntie’s panties, but I want you to see just how pretty a real girl’s lingerie is! Not nasty and frilly like yours, but grown up and sexy! Here take a look at my favourite French Knickers, smell them like a good girl and give them a nice fold! I want you to treat my lingerie with respect and love, after all they’ve touched my naked flesh, haven’t they? Would you like to touch me, sissy, touch my soft skin, with your lips and lick the sweat from my body?”
I tried to act cool, but she just laughed and told me that if continued to please her, she would allow me the honour of licking her sweat from her body. She told me that I needed a hard bare bottomed spanking, as a matter of form and did I want to be spanked on the backs of my thighs or on my bottom. I tried to indicate that I didn’t want any more punishment to my already throbbing thighs, but she ignored my silent pleas, telling me that I should be happy to have a woman give me an honest to god thrashing, for my own good. She pulled me over her lap, dragged my knickers down and passed me a pair of her dirty tights.
She ordered me to lick her tights, paying special attention to the feet and crotch area. She lifted my dress and petticoat out of the way and commenced my discipline. Auntie Gemma had me crying like a little girl by the 9th smack, so when Mommy entered the room during my 34th smack I was a blubbering mess. She watched my chastisement with a smile on her face and watched me lick and suck those dirty tights. I was made to thank my Auntie for teaching me a lesson and she pulled up my knickers, pushed my pink latex pacifier in my mouth and tied around my neck.
I stood up, gingerly and curtsied to my Mommy. My legs were very unsteady, but she pulled me to her and spun me around, taking in every item of my clothing. She caressed my petticoat, lifted it up and giggled at my bright red thighs. She asked Gemma if I’d been good and she told her that I’d been extremely obedient, but that she just thought that I needed a hard spanking. Mommy agreed and told me that she would also spank my naughty bottom now. I was quickly pulled over her lap, my knickers pulled down to my knees and my dress and petticoat lifted out of the way. Mommy took her time, softly rubbing my red thighs before tickling my sissy hole.
“I told you that he’d look like a very girly sissy and you’ve done brilliantly with him Gemma! He’s as pretty as a picture and I know that he wants to be dressed like this because he’s loving it! He’s perfect for dressing in knickers and petticoats, but he needs to be reminded that there’s a price to be allowed to be in our presence! Chris, or should I call you Chrissy now, you look totally ridiculous, but if I was to let you bathe and dress me later, you’d have to understand that you are without a chance of sexual contact! The only time I want to feel your nasty hands on my naked body, is when you wash, moisturise and dress me! You’re disgusting and I expect you to understand that I will never see you as anything more than a loser! Are you crying, Chrissy? You are, well I said he was more like a 3 year old girl and he’s showing us, isn’t he Auntie Gemma?”
I was horrified at Mommy’s vicious tirade and I looked at my Auntie for support, but she echoed Mommy’s humiliating talk. She told me that I was contemptible. She told me that I would never be allowed to spurt ever again and I should just forget about trying to be anything other than a little sissy girl. I whimpered, but then screamed when Mommy started to spank the backs of my thighs. I was beaten for what seemed like hours, but when I was pushed from Mommy’s lap I just sobbed and sobbed. Mommy looked at me with contempt and asked Auntie Gemma if she’d ever seen such a pathetic display. She stood up, dragged me to my feet and had me curtsey to my Mommy.
I was in shock, but obeyed and Auntie lifted my petticoats. My upper thighs, above the tops of my silk stockings were bright red with purple blotches. Mommy told me to bend over and show her my bottom. I obeyed, just like Auntie had taught me and I was displayed for her pleasure. She sniffed my knickers and told me that only proper sissy’s wore perfumed knickers. She seemed to glow with the sight of me in my French Maids uniform and she asked me if I was ready to serve her. I curtsied and she smiled at me. She produced the leash she used earlier, reached under my petticoat, inside my knickers and attached it to my chastity.
I was led along the upstairs landing and into Mommy’s bedroom. She pointed to a large door and asked me if I would like to see her bathroom. I nodded with trepidation and was dragged inside a lovely pale pink bathroom. Mommy pointed to her toilet and asked Auntie Gemma if I had earned the right to become a toilet slave. My Auntie hemmed and hawed, looking me up and down. She remarked that I was showing signs of being a truly submissive sissy, but clearly needed constant supervision and discipline. Mommy pulled me over to her pulled me to my knees and ordered me to take a closer look at her toilet.
“Mommy needs her nasty little sissy girl to be in no doubt that she is mine to own and the best way to demonstrate your desire to serve me is to become my personal toilet slave! So why don’t you show both of us just how much you’re willing to degrade yourself, to be humiliated and scorned! Lift up the lid with your naughty sissy mouth and lick my toilet seat! Let’s remove sissy’s pacifier and watch her clean my toilet with her tongue! Can you do anything more disgusting, Chrissy and still pretend to be human! You’re my property and don’t you forget it!”
I was to be totally humiliated in front of these 2 beautiful, dominate women and I was more than willing to obey Mommy’s perverted command. Auntie Gemma removed my Pacifier and caressed my cheek, telling me to be a good little sissy girl and do as my Mommy tells me. I bent over, my knickers on display and used my teeth to lift the toilet lid. The seat was right in front of me and I slowly licked Mommy’s toilet seat. She laughed and told me I was very naughty. She asked Auntie Gemma if she’d ever seen such a dirty display by a sissy and she told her no.
Auntie Gemma squatted down beside me and placed her hand on the back of my head. She slowly guided my journey around the entire seat, as Mommy called me a disgraceful little pervert. I was being humiliated at the most profound level, made to become nothing more than a toilet licker and my cock was leaking like a faucet. Mommy noticed and pointed it out to Auntie Gemma. She seemed amused at my display.
“Well you’re clearly enjoying you service to Rebecca’s toilet, your knickers are soaked and we’ll need to change you into some dry 1’s afterwards, but before that I’d like you to really humiliate yourself! Would you be willing to totally abase yourself and show us just what you’re willing to do in our service? You are, good, I want you to lift up Mommy’s toilet seat, with your teeth, reach your head inside the bowl, lick the pan and then drink some of the water! It’ll be completely disgusting, I’m sure, but you’d making me wet by doing it! You could satisfy any woman with your pathetic cock, but watching you lick that toilet is turning me on! In fact I’m just going to masturbate, watching you lick and drink!”
I could hear Auntie Gemma’s wet pussy, as she masturbated and couldn’t let her down, so obeyed my Auntie. I was desperate to spurt as my whole body shook with adrenaline and I reached into my knickers, to finger my bum. Mommy slapped my hand away, telling me to concentrate on my duties, but I felt her hand reach inside and tickle my bottom. We were quite a sight, I was dressed like a little sissy girl French Maid, licking a toilet, my Mommy was fingering my bum and Auntie Gemma was in the throes of a massive orgasm. Auntie Gemma pulled my head from the bowl and told me that I was a complete pervert, but she smiled as she said it.
Mommy seemed to be the most shocked at my performance, as she gently fingered my bum and I asked her, in a lisping little girl’s voice, if I’d done an adequate job. She patted me on the head and told me that I was in need of a strict and severe caning for doing such disgusting things in front of ladies, but that she would let me off if I got cleaned up quickly and prepared her for her client. I was whisked upstairs, to my room, by Auntie Gemma. I brushed my teeth, cleaned my face and reapplied my tear streaked make-up. When I walked out of my bathroom, Auntie Gemma was waiting, a pair of little girl’s knickers’ in her hands.
Made from double layered white bridal satin and edged with pink frilly lace, they were magnificent. She handed them to me and pointed to the front. ”MOMMY’S TOILET LICKER” was stitched on the front and obviously referred to my performance in Mommy’s bathroom. Auntie Gemma explained that Mommy had had them made especially and expected me to wear them this evening. In fact she hoped that I would be willing to clean her toilet later, after all I was clearly In need of further humiliation. I nodded my head and she grinned. She helped me into my knickers before we returned to Mommy’s bedroom.
“Chrissy, run me a nice hot bath, with lots of bubbles and hurry up! In 2 hours I need to be on my hands and knees, sucking cock and taking a second in my pussy! I’m getting spit roasted by a couple of massive black guys called Marlon and Clive! Best £500 fuck of my week! Gemma you’d love to spend some time underneath these guys getting fucked silly and making a few quid as well! Maybe I’ll bring Chrissy a present back, would you like me to collect my lovers used condoms? They’ll be filled with lots of creamy spunk and you could keep them as souvenirs!”
Was there no end to Mommy’s humiliations, as she giggled at her own suggestion and told me that I could start a collection of her punters used birth control. After all, I wouldn’t need to use any, as I had no chance of ever impregnating a woman. The both laughed at my lack skill in the trouser department and wondered if that was why I so easily took to wearing lingerie. Auntie Gemma entered the bathroom and asked me to come show Mommy my knickers.
I entered her bedroom to find her masturbating on her bed. She was using a large vibrator and was moaning. I looked up her skirt and saw her pussy for the first time. She was very wet, dripping wet to be correct and she asked me if I was wearing my special knickers for her. I lifted the front of my petticoat and showed her the message. She laughed and told me that I was in need of a little bit of encouragement. She patted the bed beside her and sat next to her, as she paid me no heed and fucked herself.
Auntie Gemma asked Mommy what she was wearing tonight and she pointed to a stack of bags at the end of her bed. Auntie Gemma opened a bag and a large pink box came out. It said La Perla and she asked Mommy if she could look. Mommy told to feel free and asked me if I would like to see her new lingerie. Red-faced and incredulously I nodded at such notice. Auntie Gemma passed me a pair of sexy black silk panties, low cut and a demi cup bra of the same style. I softly took them from Auntie Gemma and tried to stay calm.
“Maybe if you’re good for Auntie Gemma while I’m gone, you can play with my lingerie, when I return and maybe try them on! Would you like to wear some of my dirty panties, filled with my juice’s and 2 black men’s spunk? You would, ok then we’ll see and if you’re very good indeed, I’ll even let you remove them from my body! Go check on my bath, sissy and I’ll be with you shortly!”
The bath was almost ready and I returned to Mommy’s bedroom, curtsied to them both and tried to tell them that I needed help. It took a few minutes, but Auntie Gemma realised that I was in need of help, so she removed my pacifier and gave me permission to speak. In a clear, lisping, little girl’s voice I begged for the use of my potty to go wee-wee and p*o-p*o. Mommy giggled at my request and told me that I had her permission to go potty. She told me to fetch it and Auntie Gemma told me that it was in the bottom of my wardrobe.
I walked upstairs and found my potty, opaque pink plastic and very sissy indeed. I returned to Mommy’s bedroom to find them waiting for me. Auntie Gemma placed it next to Mommy’s sofa and sat down. She asked me to come to her and she pulled down my knickers. They were down around my ankles, as she helped me sit down on my potty and took my hand. Mommy reached down and lifted my petticoat out of the way, giving them both an unrestricted view of my evacuation. I was shaking and shivering, with shame as I tried to desperately go, but with both of my tormentors watching me with savage grins, I was intimidated. Mommy asked me if I would like to be alone and I begged her for the chance to be alone, but she was without mercy.
“Not a hope in hell, Chrissy! We both want to control your access to any type of a normal life and the best way to break you, is to control your toilet use! No more privacy, just a series of humiliating begging on your part and we will make you squirm in shame! Potty time, Chrissy, show us what a good girl you are and fill your plastic toilet! God your real a cry baby, aren’t you? Waterworks won’t save you now, so show us that you’re a dirty little sissy girl and fill your potty for us! Pathetic!”
I cried at Mommy’s tirade, but I was in no state to hold out any longer and lost control. With Mommy and Auntie Gemma watching my every move I wee-wee’d before letting a loud fart go and p*o’ed in my potty. I was mortified, as they laughed at me and asked if I was finished or did I need to go some more. I begged them not to shame me, but Auntie Gemma told me that she took great pleasure in watching me be humiliated, knowing that I both desired the feeling and hated it at the same time. She asked me if I wanted my bum wiped and nodded as they removed even that act from my control.
Mommy lifted my dress out of the way and Auntie Gemma wiped my dirty bum, with some baby wipes before pulling up my knickers and primping my dress. She returned my pacifier to my mouth tied it around my neck and stood me over my potty. Mommy asked Auntie Gemma if she’d ever seen so much p*o come out of a little girl’s bottom and I cringed as they discussed my p*o. Auntie Gemma even asked me if I wanted to have her take control of my toilet needs full time. She was adamant that she could come to my home 3 times a day and bring my potty. I looked at her with horror, but we were sent downstairs by Mommy to get rid of my mess in a basement wet room.
We returned a few minutes later to find Mommy inpatient for her bath. She ordered me to undress her and with trembling hands I removed each item of her clothing, until she was naked in front of me. With no regard to the presence of a man she seemed to be completely in control, in fact she asked me to pick up her dirty panties and fold them neatly or she’d have Auntie Gemma cane my naughty bottom. She walked into her steamy bathroom and slid into a warm scented bath. She pointed to the floor next to her and I knelt down. She passed me some soap and told me to wash her. Trembling I obeyed.
“I make you nervous don’t I Chrissy, make you feel all week and desperate to be under my control? Don’t you know by now that I’m being paid to treat you like this, make you suffer and cry like a little girl! Do you want it to end? It could you know, you could leave tomorrow and never contact me again, but you won’t will you? I’ve turned you into my bitch, haven’t I? Your Mommy’s little sissy bitch and you love it! Make sure you pay special attention to my pussy, I want to be clean for cock later and maybe you better do my bum as well! I love big cocks up my bum, spurting and filling me like a slut!”
I tried to control my breathing as I gently cleaned my Mommy’s sexy young body, her gaze on my hands, making sure that I didn’t take liberties with her person. She told me that I should shampoo her hair now and make sure to keep the soap from her eyes. I worked the shampoo deep into her dark hair before drying her hair with a big fluffy towel. She said she was ready to get out and I should dry her off. Dripping wet she towered above me, as I dried her body, her attention elsewhere and I was in heaven. For those of you who have never bathed a woman, you’ve missed out on an erotic experience like no other. To touch a woman, intimately, sensually, but not to have hope of her allowing you to be any type lover to her is totally maddening and I was shaking with desire.
Mommy walked naked into her bedroom picked up a hair dryer and turned it on. As she dried her hair, I prepare her lingerie and clothes. I picked out her deodorant and perfume before sitting at her feet. When she finished with the hair dryer she ordered me to moisturise her body. I looked at her with desire, but she sniffed and told me that I was beneath her. As rubbed in that greasy substance Auntie Gemma re-joined us and asked me if I would be willing to bathe and dress her later. I nodded my head enthusiastically.
“I needn’t have even asked, you’re obviously destined to serve women in a very unique way and the fact your cock is securely locked away, makes for a much more tractable sissy! Control a males orgasm and you turn him sissy, control its toilet use and you humiliate him, turning him into a toilet licker is the ultimate! Watching you drink Mommy’s toilet water was so good, so if I ask you to lick my toilet later and masturbate, you’ll be in heaven! Sexually, I’ve never met a person that I less wanted to have sex with, but when you show us that your dirty little slut, I get so wet! I just masturbated for the 3rd time today and I’m still horny!”
I was unable to contain myself anymore and dribbled my spunk inside my knickers like a whore. Mommy saw and smiled at my shameful state. She rubbed my damp knickers and asked me if I’d finished acting like a pervert in her proximity. I hung my head as Mommy told me that I was very naughty for dribbling in a second pair of knickers and I needed to be punished, after I finished her skin routine, she bent me over the end of her bed pulled my wet knickers down, picked up a stout cane and gave me 6 of the best.
Auntie Gemma watched as I was taught to control my sissy ways with a hard brutal punishment. Mommy dragged me over to her mirror and showed me the damage she’d done to my bottom. 6 livid marks criss-crossed my bum and I cried like a little girl. I was still crying as I perfumed, powdered and deodorized Mommy’s body. She’d left my knickers around my ankles, to remind me to behave like a good girl. For a few minutes, both I and a beautiful woman were pantie less, but I was in condition to do anything in fact, I was both humiliated by my state and in need of a hug, but I would have neither. Instead I dressed my Mommy.
“Put Mommy’s lingerie on, Chrissy and I’ll make you a deal. I’ll have Auntie Gemma use a very special device on your sissy hole and milk all that nasty spunk out of your swollen balls! You won’t spurt, but you’ll feel so much better with less spunk in you and she’ll make you feel like a nasty little slut! Now don’t pretend that you don’t need a nice milking, Chrissy, you’ve made 2 nasty messes in your knickers already and I expect more shameful acts when you bathe Auntie Gemma! She’ll be naked in front of you, you can look and you can wash her sexy body, but when you shamefully leak in another pair of knickers, she’ll cane you again, but double the amount! A dozen stripes or a nice girly milking instead, what will it be, Chrissy? A milking, good choice, Gemma use the special milking probe in Chrissy’s room and be sure to collect every drop! Why, sissy? You’ll drink up every drop when I get home and I’ll make you do it so slowly, like a slut and whore! Like me!”
Mommy’s lingerie was on, but she shooed me away telling me that I was to slow and she was running late. Auntie Gemma took me upstairs and picked out a pair of barely there knickers. Opaque pink glass silk, I was unable to hide my shame as I asked Auntie Gemma if she was really going to milk me. She giggled and told me that she’d love to, in fact she reached into a draw and pulled out the special probe. Made of very soft, thin pink latex, it was very bendy and long. She handed it to me and asked if I needed to restrained for my milking or would I be a good sissy and not try and touch myself.
Shuddering, I told her that I’d be on my best behaviour. She promised me that I’d be unable to control myself and she probably better tie me up. I was barely able to walk as she bought me into her room and prepared me for a milking. She tied my hands and feet to the 4 posts of her bed, with some of her dirty tights and stockings. She pushed a pillow under my bottom, giving her easy access to my hole. She picked up a glass from beside her bed and told me that I’d be filling it up to the top. She pushed the probe into a jar of Vaseline and very gently eased it up my bum. I writhed in sissy pleasure as Auntie Gemma probed and explored my bum. She looked at me through my spread legs and smiled.
“See you need to be restrained for your milking, didn’t you? God you’re a horny little slut aren’t you, but not to worry, Auntie Gemma will soon have that nasty spunk out of your big balls and into a glass, so you can drink down for Mommy later! Bet you feel so girly right now, don’t you? I’m loving this, Chrissy, loving making you squirm, but I’ll let you into secret, you’re going to dribble in a second! Don’t worry if you don’t feel like you’ve done a normal spurt, as this is so much better, no orgasm, but you’ll feel almost like a girl as you drain and I’m going to catch it!”
She bought me to the brink, over and over again, never letting me spurt, but milking my prostate with deft touches of her probe. In fact when Mommy came to say goodbye, I was begging her to please let me come. I was in utter despair at the feeling of being under the control of Auntie Gemma, so when Mommy sat on the bed beside me, I was close to hysterics. She leant down and kissed me on the cheek, in a parody of a real parent and asked me if I was suffering. I told her that I’d never been so horny in my life and I needed to spurt. She just laughed and said no chance. She told Auntie Gemma to slow it down even more, make me squirm and wriggle for her and when I was drained dry, show me just how much I’d filled the glass.
She lifted her short leather skirt, showing me her panties and hold up stocking tops. She said goodbye and told me that the thought of me suffering right now was splendid. She whispered in my ear to enjoy my milking, as it wouldn’t be happening again for a month. A month of blue balls and horniness, but I was nothing more than her nasty little sissy girl and deserved every moment of agony. I asked her if she would please do me a favour, she looked at me with stern visage and asked me to spit it out. I pleaded with her for a chance to see her meeting this evening. She looked at me quizzically and I asked if she would please film her taking to big black cocks, so that I could see what I was missing.
“That sounds like a great idea, Chrissy, but are you sure, I mean you won’t be humiliated to see me under the control of a couple of big black guys, taking their cocks in every hole and swallow all there spunk! Okay then, I’ll film it on my phone and we can watch it together, when I come home and when it’s finished you can drink down all that nasty spunk, dribbling from your pathetic cock! Waste not, want not, after all and you should be willing to do anything later! Enjoy, sissy!”
She slinked out of the room and I was left alone with Auntie Gemma, as she deliberately and cruelly, turned me into a quivering wreck. For nearly an hour she milked me dry and when she could no longer get a drop out of me, she showed me a nearly half full glass. A glass I would be drinking later. She left me tied up and went to put my slimy cocktail in the fridge. She returned a couple of minutes later, my potty in her hand and a smile on her face. She shushed me and told me to calm down, but she wanted me on my potty. I begged her not to be so cruel, but she was without an ounce of shame as she untied me. She helped me up and with shaky legs and no knickers, I was soon siting on my potty.
Auntie Gemma sat right in front of me, her legs resting on my shoulders as I lifted my own petticoat out of the way and to give her a clear view between my legs. She was playing with herself and I would be her live pornography. I was a living, breathing being, but when I asked her to please show me a little respect she laughed. She reminded me that she’d just got me off and now it was her turn. I told her that I was still incredibly horny and begged her to let me spurt. She giggled and spat in my face. Her saliva dripped down my face as she began to pant from her efforts. In fact she was very close to coming.
“It’s time, Chrissy, potty time, so be a good girl and go wee-wee for Auntie Gemma! Go on and afterwards I’ll dress you for bed, all frilly and girly before I have you lick my toilet clean! Oh god, you’re such a tease aren’t you, no wonder Rebecca locked your cock away for good, but don’t pretend that you don’t love watching me masturbate! Let’s do it at the same time, you wee-wee and I’ll orgasm! That’s a good girl, on the count of 3-2-1-go!”
As I wee’d in my potty, Auntie Gemma orgasmed a foot from my face, she was loud and very, very vocal. I begged her to please help me off my potty, but she just smiled and asked me if I liked using a potty. I told her that it was very humiliating and she told me that was the point. In fact, I was so in need of being degraded by her that I should be paying her as well. I looked shocked that Mommy wasn’t paying her and when I told her that I’d be willing to put her on a retainer to take care of my needs on a more permanent basis she asked how much. I asked her how much she made doing her day job.
“I’m a part time care worker and barmaid, so I bring about £400 per week home before tax, but if you make it worthwhile, I could easily become your fulltime Auntie! £5000 per week, a clothes allowance and free board! Sounds perfect, but you should understand that they’ll be no chance of hanky panky, just unrelenting teasing and humiliations! I expect to be waited on hand and foot by you and you’ll be dressed in the most girly outfits! No more pretence of being a make, just frilly knickers and petticoats! Give me 2 weeks to work out my notice and we’ll sissy and Auntie! Now be a dear and go empty your potty because I want to get you ready for bed!”
Dazed at the swift change that Auntie Gemma was making in my life, I nevertheless felt a strong desire to be in a relationship that made me into what I deserved to be. A dirty little sissy girl, so when I returned my potty to her I dropped to the floor, kissed her feet and begged her turn my life in to a humiliated nightmare, for her amusement. I begged her to become my ultimate temptress, to play mind games and I’d spend every day trying to please and serve her. I looked up at her and she smiled. She was clearly delight with my declaration and when I promised her £50000 signing bonus she squealed.
“Wardrobe will be key I think, lots of scrummy sissy dresses, lingerie and petticoats, but I don’t know what I she dress like. Do you have any preferences, sissy or should I just dress sexy? How about a theme, at least for most of the time, I could dress as very dominant nurse, you know latex and P.V.C. uniforms, thigh high boots and no panties! Lots of kinky medical play, enema’s and anal exploration, but also lots of mistress gear and naughty lingerie, maybe even a sissy school. I’ll be sure that your potty is always close at hand, for your number 1’s, 2’s and 3’s! A big sissy like you should milk in his potty don’t you think, your bum in the air, as milk your prostate and fill up your potty with your nasty spunk!”
She hugged me and told me it was time to dress for bed. She led me upstairs and told me to strip off everything while she got everything ready. I stood next to her, naked but for my chastity and stared at her choice. She’d picked a darling pink plastic opaque onesie, with a picture of a fairy on the front and a very frilly behind. She’d chosen less conventional lingerie, a stared at a large pink cotton diaper and frilly pink rhumba panties. Auntie Gemma was putting me in diapers. I begged her not to shame me anymore, but she was adamant. In case of naughty accidents, overnight, I would be heavily diapered and I should worry more about my onesie.
She picked it up and I heard the material crinkle. She warned that I wouldn’t be able to try anything when I’d be heard from 20 metres away and if I wasn’t convinced she showed me the opening at the behind. Pop open tabs allowed for easy access and she’d love to change my dirty diaper, in fact she bet me that I’d be very smelly come morning. She asked me if I liked my bedtime clothes and I told her I wasn’t sure. I asked her what Mommy would say when she saw my big fat diaper, but she laughed, called me silly and told me that Mommy had suggested it.
I was laid down on a pink P.V.C. changing mat and my grinning Auntie prepared to put me back into diapers. She poured baby oil on to my crotch and massaged my aching balls before slowly pushing 2 of her fingers in to my bum. She giggled and told me that baby obviously like it when Auntie played with her hole. She continued my fingering, as she powdered my bottom before picking up my diapers. She ran them across my bottom and I felt just how soft they were. Soft as a baby’s bum and I would be the baby. She lifted my behind and placed them underneath. I settled down and felt the incredible softness. She positioned the diapers and using Tinkerbell diaper pins I was once again little baby.
“Wow, they look perfect on such a big sissy like you and will definatly be making you into my frilly little sissy baby frequently! I don’t want you to worry, Chrissy, but you’re not wearing plastic panties, but Auntie Gemma has these lovely pink plastic lined rhumba panties just waiting for you! You can stop worrying about leaks while you have these on and I’m sure you’ll love just how frilly they are! See 7 rows of ruffles on the behind and around the leg holes and waist! Now lift up your bum and I’ll pull them over your diapers! Here you go, suck on your pacifier while I finish dressing you! God, I could just eat you up!”
I stood up and saw myself in the mirror. I was a grown man wearing a pink diaper and pink plastic rhumba panties, I was sucking on a pacifier and I was horrified. Auntie Gemma stood behind me and caressed my bottom, she giggled and told me that I was really cute, but I needed my lovely onesie to really feel babyish. She pulled it up my body, using lots of baby powder to ease the way and very quickly I was buttoned in my onesie. Auntie Gemma was clearly revelling in my humiliation and when she picked up my frilly tutu, I started to cry, she hugged me tightly and asked what was wrong. I told her that I looked ridiculous and she agreed with me. She asked me if I really wanted to lick her toilet clean and shamefully I nodded.
She told me that she only allowed diaper wearing sissy’s to lick her toilet, so I better shut up and get with the program. She fastened the tutu around my waist, before attaching a pair of wings to my back. She placed a pair of pink plastic mittens on my hands and I lost the ability to do much with my hands. She pulled my hair out loose and pinned a pink plastic garland of flowers in my hair. The last piece of my costume was pink glittery wand. I was in shock, but Auntie Gemma used the moment to full effect. She opened up the rear access, in my onesie, pushed her hand down the back of my diaper and once again fingered my bum.
“God you look pathetic! Fancy letting me dress you as adult baby fairy! What would people think if they could see you now, dressed like a fairy, sucking on a pacifier and his Auntie fingering his naughty bum! Do you think they’d laugh at you? I know if I saw you on the street dressed like this I’d point and laugh, so I guess I should do what comes natural! Go ahead and cry all you want, but I’ve had enough of your pathetic attempts to change my mind so let’s get you downstairs and licking my toilet!”
She frogmarched me downstairs, her fingers never leaving my bum for a moment, until we stood in her bathroom. She pointed to the floor and sank to my knees, gratefully, as Auntie Gemma pulled of all her clothes. She was nude and I was under her spell as she asked me if I thought she was pretty. I nodded my head, vigorously and she asked me if I would like to fuck her, just the once and lose my virginity. Again I nodded, but she was playing mind games again. She sneered and told me that I would never have a chance with any woman while I still wore diapers.
Telling me that I was not much of a catch anyway, but dressed as I was I shouldn’t even be talking to a woman as hot as she was. I looked at her with longing and she sneered at me. She pointed at her toilet and asked why I was stalling. I shuddered, leant over and lifted the lid with my teeth. The seat was brilliant white, except for a single pubic hair. She asked me if I would like to have permission to kiss her discarded pubic hair and shivering I nodded. She told me that I was very lucky to be able to see her pubic hair and even more fortunate to kiss 1. I puckered up and with Auntie Gemma looking on in kissed her pube. She gave me 3 kisses before she took it away, telling me that I should feel free to start licking. She knelt beside me, naked and I felt her hand making its way back inside the rear of my diaper.
“You’re a natural at this, Chrissy and I intend to spend quite a few hours each day, having you clean my toilet with your tongue! Every inch mind and 3 times a day, as well, you do want me to have a sparkling toilet at all times, don’t you? Well you’ll need to apply yourself and don’t expect to use it for your nasty evacuations, I’ll be having you use a nice potty, well maybe you’ll fill your diaper for me as well! Don’t worry Chrissy, I won’t tell anyone about your nasty problem, I might show them, but I won’t tell them and so what if a few of your neighbours help change your dirty bottom on occasion, they won’t laugh too much! You missed a bit, just there, good girl, Chrissy, but let’s lift up that seat and have you lick the porcelain as well! I think you should do the floor around the bowl as well, you know to clean up any splashes or mess!”
I was in utter sissy hell or heaven, I couldn’t tell, I just knew that I wanted Auntie Gemma to keep fingering my bum. She seemed almost lost in the action, as she made shudder with ecstasy. I was her glove and when she pushed 3rd finger up my sissy pussy I moaned like a slut. She asked what was wrong, but seemed to have forgotten all about her frottage of me. She had me lick under the seat, paying special attention to the hinges. I licked and licked as I was masturbated like a girl. I shuddered and Auntie Gemma whispered in my ear that I should shush or she would make me pay. She asked me if I’d like a caning, for her pleasure and to masturbate over. I shook my head, but she wouldn’t let up , asking me to please let her cane me.
I tried to tell her no again, but she slipped her fingers from my bottom and pushed my head down towards the water. She told me to lap up her nice water, like a good slut and told me that she was going to cane without my agreement because after all she was in charge. I sobbed as she dragged me into her bedroom, bent me over the back of sofa and pulled my diapers down. My bum showed through the hole in the rear of my onesie and shuddered at what I was about to take. She picked a short whippy cane and with no warning lashed my bottom. It was much less painful than Mommy’s caning earlier, but Auntie Gemma was taking her time. She hit me slowly, varying pace, angles and power. I looked back at her and she winked at me. Her free hand was openly inside her dripping pussy. She was getting off on my pain.
“I love punishing your bum, Chrissy and I think you should understand that I intend to be a very strict Auntie! No more playing around, once I take over your life, as I intend to discipline you frequently! Bare bottomed spankings will be the norm, but I’ll give you a really hard caning every day! Do you know why, sissy? Because I can, because I’ll own this perky bottom and I’ll take great pleasure in making you sob for a ladies pleasure! I’ll masturbate, as I beat you and that will be so fun, won’t it? Your pain is my pleasure and if you complain, I’ll just take you out for the day, to the mall perhaps, dressed in diapers and a very short dress, you’ll be on public display! Don’t think I won’t, Chrissy, I’ll strap you in a push chair, take you lingerie shopping and show every young girl just what’s inside your diaper! Pray that it’s only a dirty diaper and they don’t see chastity covered cock! I’m almost there, sissy, so feel free to bawl like a toddler because here comes the pain!”
She began really lay the strokes on and I hopped and sobbed in agony. It was soon over and she lifted me onto the bed and fixed my diaper and rhumba panties. She held me like a real baby before she allowed me to suckle at her breast. She giggled and told me that I clearly need to be in diapers, as I kept crying like a little one and now want to be breast fed. She tickled my cheek and made very disturbing baby talk, making feel very dirty and nasty. She asked me to fill my diaper and she’d ask Mommy to let my cock free for 20 minutes when she returned. I shook my head no, but she just told me that she understood, that wearing girls clothes and being milked made up for masturbating and if she was in my shoes she’d never humiliate herself for a wank.
She giggled and reminded me that she wouldn’t be the 1 who owned his cock once she moved in, Rebecca would still have that privilege and she wouldn’t be able to get access to it. In fact she was adamant that she would look into lock me away permanently. Perhaps a little superglue in the lock and they’d be no more begging for spurt’s. She whispered that it wasn’t important after all, she’d be happy till milk me once a year, on my Birthday, if I wasn’t naughty. She made it almost impossible to take her gentle reminders that I was at her mercy and if I was going to spend every day under her supervision from now on, I’d better obey her whims. She giggled and asked me to fill my diaper like a good girl and I could bathe her. She bought her left hand to my face and I could smell her pussy on her fingers. I nodded slowly, as she beamed at my surrender, she sat up pulled me onto my lap and told me to go potty.
“What a kinky little girl you are, Chrissy, fancy filling your diaper like a proper baby! It’ll be our secret though, I won’t tell anyone that you messed yourself, so don’t worry about that, but you should hurry up and do it! Don’t pretend that you don’t need to go, I can feel your wriggling bottom on my lap, so suck your pacifier and let it out! I’m so pleased that you can be so open around me, not many men can wet themselves in front of a woman the met only 11 hours ago, but as soon as I saw you, I could tell! That’s it Chrissy show Auntie Gemma what a good girl you are!”
I couldn’t hold out and in seconds, I filled my diaper with lots of wee-wee. Auntie Gemma, giggled and asked me if it was as good as spurting. I didn’t understand, so she explained that Mommy had already promised that I wouldn’t be allowed out of chastity for a minimum of a year. She considered me to be far too naughty and if I thought I had a chance of using my cock again, I’d be using prostitutes and pretending to be a real man instead of a sissy. She’d tricked me again and just looked at her with horror. I had a wet diaper, but Auntie Gemma would only change me when Mommy returned home so I could expect to be very dirty and smelly by then. She pushed me from her lap and told me to draw her bubble bath.
Whimpering and with a very soggy diaper I drew her bath and waited for her to enter. When she did she had a very large baby bottle in her hand, filled with milk and tipped with a rubber teat. She removed my pacifier and told that she wanted me to drink it. I sobbed that I was sorry and please could she stop being so horrible. She hugged me, her naked breasts pushing into my chest and her wet pussy against my wet diaper. She told me that I was very naughty and was I need of some very strict and humiliating moments if she had any chance to make something of me. She told me that I was being silly and if I didn’t drink my milk, she’d make me spend all night in my dirty diaper. I sobbed and she stroked my hair telling me that I would all be better soon. She lifted the bottle to my lips and held it there till I finished every drop. She patted me on the back before removing my mittens. It was bath time.
“I want you to clean every inch of my body, Chrissy and make sure to clean my holes properly! Hurry up sissy I haven’t got all day and neither have you! Mommy will home in about an hour and I want to downstairs waiting for her when she returns! Wait till you see my lingerie, you’ll be so envious of my panties and stockings, but you’ve clearly need to be regressed to a more submissive age, haven’t you? No more decisions for you just diaper changes and sucking your bottle for Auntie Gemma! Don’t worry though, I’ll still give you a big hug and sooth you when you get scared, but remember to be properly submissive when Mommy returns! She likes to spank naughty sissies and when I tell her that you’ve wet your diaper, you’ll be in real trouble! I bet she spank’s you over and over again or maybe she’ll cane you or if she’s really upset she’ll drive you out to a park, chain you to lamppost, hang a please fuck me sign around your neck and drive off!”
I begged her to stop teasing, but she giggled and told me to be quiet and pay attention. She thought she had heard something and just then the bathroom door opened and in strode Rebecca. She burst out laughing as she asked Auntie Gemma if had been a good baby or a bad baby. She looked at me with pity and I thought for a moment that I had gotten through to her, but I was without a friend in this room. She pointed to my visible diaper and asked Mommy to check out what I’d done. Seething she pulled me to my feet, opened the flap at the rear and sniffed my diaper. The smell of cold wee-wee was evident and I begged to be changed. Mommy told me to follow her and took me upstairs to my room helped me out my onesie. She laid me on my changing mat and soon had me naked. She cleaned me up with baby wipes and the powdered my bum.
She spanked my bum really hard 4 times and looking through my legs asked me if I was deliberately being naughty. I pleaded that I was a good girl, but she smacked me 4 more times. I begged her to stop put she told me that I needed a jolly hard spanking and that she would administer it right now. Mommy smacked my naughty bottom and made me cry. She had me suck on her other hand, telling me that I had just about lost any chance of being returned to a normal life. I told her that Auntie Gemma had agreed to become my live in Auntie and I was fortunate that such a beautiful woman was willing to put up with my perverted life. She asked me if I would like to be diapered again, but dressed in a frilly girls dress for the rest of the night. I nodded and Mommy asked if I would be willing spend 1 evening a week at her home as her Adult Baby French Maid. Diapered and wearing a pinafore, I would have the honour of cleaning her toilet and hand washing her lingerie. I begged her to allow me to be involved in serving her in any way she deemed appropriate.
“Licking toilets is perfect for a dirty little sissy like you and having you on your hands and knees using your tongue to clean my toilet seems just right! I mean you’re obviously obsessed with toilets, you’ve started wearing yours, haven’t you? Right let’s put you in a nice soft diaper and some cute plastic panties, shall we? These are lovely, aren’t they, all little girls dream about wearing such frilly panties under their party dresses, but not many boys get the chance, do they? Now bum up sissy and let’s pin on your toilet! Very nice, but not complete yet, so spread your legs so Mommy can put your plastic panties on and make you completely waterproof! I love the picture of the duck on the front, but I don’t think the dress and petticoat I had in mind will hide just how big a diaper you’re wearing! Good job only Mommy and Auntie Gemma are here or you’d be so embarrassed!”
With my plastic panties on, I was soon dressed in a ridiculously short dress, style like Little bro Peeps dress. Made from shiny powder blue silk and dripping with white lace, I was the total sissy for my Mommy. The petticoat lifted the skirt horizontal and my diapers were on full display. Frilly white silk and lace ankle socks, protected my feet from the black patent leather Mary Jane’s. My head was covered by a massive blue bonnet, tied on with a big floppy bow under my chin and I held a wooden shepherds crook in my white lace fingerless glove covered hand. Mommy opened a draw and pulled out a very girly box, she passed it to me and told me to open my new pacifier. It was hideous, made from soft pink plastic and the teat was made latex, shaped like a cock, 3” long and 1” wide. I looked at Mommy in shock, but she just smiled and told me that I needed to learn how to suck cock like a good sissy and since I spent most of my days sucking a pacifier she’d decided to combine both activities.
She pulled a pair of pink leather baby reins, from within my wardrobe and fastened my into them telling me that a little baby bondage was long overdue. She asked me if I’d liked being tied up when Auntie Gemma had milked me earlier and I shook my head, as Mommy slowly pushed my cock pacifier into my mouth and fastened the ribbon in a pretty bow. Mommy asked me if I had been loose during my milking if I would have able to take. Blushing I shook my head and she guessed that a pathetic little pansy like me needed to be restrained during a long hard milking. She took my reins and bought me back to Auntie Gemma’s bedroom. Mommy told me wait there while she went and spoke to Auntie. I heard Mommy talk and a peal of laughter. Mommy came out and told me to help Gemma.
“Don’t be shy, Chrissy, Auntie Gemma look at her brave sissy baby! Wow, Mommy’s made you into a very cute shepherd and are those diapers even bigger than the 1’s I had you wear earlier? They are you know, but you’ve demonstrated that we can’t trust you to be a big girl, so you’ll have to be diapered from now on! Don’t be sad, Chrissy, I’m sure in a few months, a year at most you’ll be ready for some nice girly knickers and using a potty! Bet you never thought you’d miss that would you, but I bet you’d love to be on it right now, doing a p*o-p*o for Auntie Gemma and Mommy, but instead you get to fill your diapers and wait for 1 of us to change your bottom! God you’re pathetic aren’t you, get my towel and dry me, hurry up I want to show you my lingerie!”
We were soon in her room and she passed me her clothes. Pair of black, silk hold up stockings, red 6” patent leather knee high boots and a massive strap on cock. 8” long and 2” wide Auntie Gemma would look dangerously erotic and every inch the dominant she was. A spray of perfume, some deodorant and a little help with her strap on and she was ready for anything. She hugged me, her cock jammed into my belly and hands feeling my huge diaper covered bottom. She took my reins in hand and led me downstairs, into the living room and straight into a 3 way conversation. Mommy wasn’t alone. She was talking to 2 other women and I gasped as I recognised them both.
The first was my former secretary from the accountants that I had worked at before my windfall. Her name was Ms. Prendergast, her manners were almost Victorian and dressed very conservatively. In her late 30’s and unmarried, I’d always assumed she was a cat lady, right up until I walked in on her with a teenage assistant named Honey. Ms. Prendergast was dressed in her lingerie, very tight corset with silk stockings and high heeled ankle boots. Her breasts were free and pierced and her pussy was bare, well except for Honeys tongue, which was deep inside. Honey was naked except for a dog collar and leash, which Ms. Prendergast was using to control what I took to be her teenage slave. She was calling Honey a dirty little strumpet and telling her that when she got her home later, she’d be whipped for her flirting. I ducked before being spotted, but from that point on Ms. Prendergast loomed large in my fantasies.
The second was only remain relative, Jenny. She was technically my step-sister so I didn’t much contact with her after our parents divorced. She was younger than me, but was the first girl to find out what I found erotic. When I was 18 and she was 15, she walked in on me dressed in her Mothers wedding dress and full bridal lingerie underneath. Just as she walked in I spurted in her Mothers bridal panties and destroyed our relationship. I hadn’t seen her since her Mother’s funeral 5 years before. After the service I turned up at the wake at her home and she pulled me upstairs and pointed to a pile of boxes. She told me to take them with me and never darken her door again. She disappeared and when I peeked inside I found all my Step-Mother’s clothes, lingerie and make-up. I took them and fled, humiliated.
Auntie Gemma pulled me into the room, a huge grin on her face as I was presented to everyone. Mommy took my reins and led me over to both ladies. They were looking at me in shock, but when I was introduced to them, wide grins broke out on their faces. Ms. Prendergast lifted my petticoat and gasped at my diapers and plastic panties. She asked Mommy if I was dressed this way for a bet and she explained that I’d been a very naughty boy, so I’d been punished by her and her friend, she told them that I’d been caught stealing panties from their clothes lines and instead of being reported to the police, I’d agreed to spend 1 year locked in a chastity device and to be feminized. I looked at both women and I could see that they accepted the lie they’d been told. Jenny looked at me with revulsion.
“Still stealing women’s panties, Chris, I always expected to see you dressed in a dress again one day but this is just too perfect! I caught my step-brother in my Mother’s wedding dress and lingerie, playing with himself, like a total pervert and spurting his nasty spunk Mother’s panties! So you’ve finally submitted to a course of strict discipline and training, I see, but I must know, does he use his diapers? He does, well I’m not surprised at all, you’re clearly getting your just deserts and I would like to thank you both!”
I wanted the ground to open up beneath me as I was put in my place by my step-sister and a very happy looking Auntie Gemma took my hand and whispered that I needed this. I needed to be exposed and ridiculed and I should revel in the moment. She suggested I apologise, but I shook my head at the idea. I knew Jenny would never forgive my trespass, but when Auntie Gemma suggested that I should lick her shoes in submission to her rightful anger I nodded. She removed my pacifier and at the last moment I remembered the cock I was sucking on. Jenny giggled as my drool covered pacifier entered the light of day and she asked me if I liked to suck cock. Red-faced and in my lisping little girls voice I asked my step-sister if I could show her my gratitude for revealing my kinky past. She smiled and asked what I intended. I asked if I could be allowed to clean her shoes, with my tongue and let her see that I was nothing more than a nasty sissy. She nodded and watched as I sank to my knees and licked her shoes.
I felt a hand on the backs of my bare legs, the evidence of my numerous punishments clearly visible and I shuddered at the scope of my exposure. It was Ms. Prendergast who’d noticed my welts and asked my Mommy what I’d done to deserve such discipline. Mommy told that I received frequent physical chastisements and deserved everyone. She explained that I’d begged for a bare bottomed spanking earlier after I’d dribbled my nasty sissy spunk past my chastity device and into my little girl’s knickers. Jenny asked what a chastity device was and Mommy explained that it prevented me from got hard on’s. She giggled when Auntie Gemma told her that I was now imprisoned in the most painful and humiliating way possible. I was unable spurt and I’d had my dignity destroyed by filling my diapers like a real baby. Jenny reached down, caressed my plastic covered bottom and said that I should be very happy to serve such strict and dominant women. She asked if I’d ever told them about stealing her Mother’s clothes after her funeral and pretending that I’d given them to him instead. Once again I was lied about but when Mommy asked if I had any defence for such a wicked crime and I shook my head, like I knew she wanted me to, she promised to punish me severely.
I was hauled to my feet dragged over to the sofa and across Mommy’s lap. She pulled my plastic panties and diapers down, exposing my bottom. She called me a dirty little thief and told me that I would be spanked for my punishment and for the satisfaction of the women present. Mommy invited Jenny and Ms. Prendergast closer, as she promised to make me cry like a little girl. Auntie Gemma pushed my cock pacifier deep into my mouth and tied tightly. I was to be publically punished and I felt my heart race in shame. Mommy asked Jenny how many smacks I deserved and she said 10. I thought how lucky I was to such a low number, but Mommy told her that I regularly took 100 or more. Jenny squatted down beside my face and looked me in the eye as she told my Mommy to punish me for as long as she deemed reasonable. I knew I would be humiliated, but when the first smack hit my bottom tears welled in my eyes and sucked even harder on my cock shaped pacifier. Jenny whispered in my ear.
“Time for you to suffer, Chris and I for 1 will enjoy every moment of your spanking, at the hands of your Mommy! Tears in your eyes so soon, but don’t worry we’ll all enjoy seeing you blubber and cry like the little girl you resemble! Does that cock taste nice, Chris? Do you like to suck real cocks and take it in your bum? You must be gay to dress like that, what you’re not and fancy women! I’m surprised! Fancy being dressed up in a little girl’s dress, diapers and sucking on cock, like a slut, as I watch! Revenge is sweet, just like those darling plastic panties and lovely diapers! Would you mind if I put you back into your diapers when your punishment is over? You do, well I don’t think you get a vote do you? All you have to do is lie back and watch, as put your red bottom in your diapers and have a close look at your imprisoned cock! I promise not to laugh, well maybe a little, but you should be relieved to lose your spurts! No more nasty hard on’s in Mother’s panties and or your diapers! Chin up, Chris and make me proud!”
I couldn’t hold back anymore and I burst into tears, crying for Mommy to stop, but only a muffled moan passed my pacifier. Ms. Prendergast asked Mommy if I was a frequent pantie sniffer, because in her experience, men who stole ladies panties were nasty pantie sniffer’s and liked to dress in women’s lingerie. Mommy told her that I was an aficionado of dirty panties and spent most days up to my elbows in the sink hand washing their lingerie, I was allowed to sniff and even lick the items of intimate apparel as I couldn’t get a hard on through my chastity device. Mommy even had me wash her used tights and stockings before letting me rub them on my balls. I kicked my legs and blubbered as I was taught to understand my place, at the feet of women and not as there equals.
Mommy pushed off her lap and landed in a heap at her and Jenny’s feet. She asked if she might be allowed to re-diaper me and Auntie Gemma thought it was a great idea. She asked me if I minded and I shook my head in the negative, but she told Jenny to carry on. I had no say in anything to do with my life. Jenny rolled me over and exposed my chastity covered cock to the room. She stroked the plastic and I shivered. She looked me in the eye and asked me if she’d like her to play with my balls. I shook my head, but she laughed and did it anyway revelling in my submission. She asked my Mommy if I was allowed any kind of relief and she told her all about my milking at the hands of Auntie Gemma. Jenny asked just how it felt to be used like that and not get any sense of satisfaction. Auntie Gemma explained how satisfied I was when was all over and she’d drained me. She told them about the glass I’d filled and wondered if they’d like to see my efforts.
As I was fondled, by my step-sister and tried to stop crying Auntie Gemma bought the results of milking to show everyone. Jenny gasped when she saw how much spunk I’d leaked and Ms. Prendergast asked why it had been kept. She grinned and told how I’d promised to drink every drop in front of her and Mommy this evening, but wondered if I’d like to have my step-sister feed it to me. I shivered as Jenny beamed at me and told me that I had better get ready for a protein shake. She took the glass and carefully removed my cock pacifier before bringing the glass to my lips. I looked at her with horror as she pinches nose so that when I open my mouth to breath, she can dribble some of my congealed spunk down my throat. I gag as I’m force feed my on spunk, with everyone laughing and my Mommy stroking my face. Mommy tells me to open wide and I’m forced to suck on my cock pacifier. Jenny diapers me and pulls up my plastic panties.
“There you are Chris, all safe in your diapers and plastic panties again! Ah, don’t worry your pretty little head, we all understand why you drank your own spunk, but do you understand? It’s about power, we have it and you don’t! I bet you would love a nice hug from me wouldn’t you? A naughty sissy like you needs a hug every so often and I’ll give you 1 in a minute, but first I’d like to show Ms. Prendergast what a cute ducky you’ve got on your panties! Isn’t it lovely and so perfect for a baby’s panties, so why don’t you give me a nice big hug and I’ll let you imagine being close to an actual woman!”
Jenny hugged me and Auntie Gemma patted me on bottom. I was passed over to Ms. Prendergast and she looked at me with utter contempt. She clearly loathed me on general principle, she was a lesbian and looked at me pretend to be female and took offence. She took hold of my reins and pulled me close. She stroked my bonneted head and asked if I had lots of girly dressed, I nodded sucking on my pacifier as she asked to see them all. I turned to Mommy and she nodded. I led the way up to my room, with Ms. Prendergast looking up my skirt and rubbing my scarlet thighs. We entered my room and I pointed to my wardrobe. For a moment I was nearly a real girl, showing off my dresses to another woman and expect her pick 1 out, but I was in for a rude surprise.
“What a disgusting collection of frilly concoctions! No real woman would be caught dead in anything as completely feminine as these things! Do you really believe that any woman would wish to dress up like this and pretend to be something she’s not? No and I’ll tell you straight, I expect to be made to understand why you’ve allowed yourself to be controlled this way at all! Did you think I didn’t see you that day when my slave was apologising for her misdeeds. She looked at another woman, in my presence and without permission, but you’ve offended me much more seriously, Chris! I’m the woman here and I expect you show just how much you desire to be allowed to spend time with me! Show me just what a sissy you are and mess your diaper for me! Drop a load in your diapers and change your sissy bottom! Maybe the ladies downstairs won’t notice your diaper change, but I’ll just have to tell them won’t I? It’s for your own good, lying to your betters is very naughty and I expect your cooperation!”
I stood all red-faced and shaky legged as my former secretary, ordered me to mess my diapers, for her satisfaction and my humiliation. I tried, but I couldn’t go with her watching me like a hawk, so she suggested that I squat and try harder. I obeyed and after a few minutes felt a shift in my bowels. Ms. Prendergast asked me if I was going to shit my diaper and I nodded, just as Auntie Gemma entered with Jenny right behind her. I panicked and lost control, my bowels opened and filled my diapers in seconds. A very recognisable smell filled the room and panicked again. More of my p*o-p*o filled my sagging diaper. Ms. Prendergast grinned at my humiliation and in a loud voice announced that I’d shit my diaper. Jenny stared at me in disgust, but Auntie Gemma asked me if I’d emptied my bowels into my very own mobile toilet. With a sob, I nodded and looked at her with the hope that she’d send the other women away and change me in private.
That definatly didn’t happen and I was soon on my changing mat, legs in the air, dirty bottom on display and being watched by 2 very happy women and 1 who looked horrified. Jenny asked if I did this often and Auntie Gemma told her that I was a persistent bedwetter and needed the safety of a diaper, even before my punishment. As Auntie Gemma wiped away my p*o-p*o, Ms. Prendergast squatted down beside me and told me that I’d done a pretty good job. She asked if would be willing to spend some time away from here, at a small exclusive fetish club she attended. She told me that I’d be the centre of attention if I messed my diapers on the dance floor, with dozens of people watching as she changed me. I shuddered at the thought, but she persisted and asked me if I would humiliate myself for her amusement. I nodded my head, as she looked at my chastity covered cock and laughed.
“The place is all female, no penises allowed, but I’m sure if you show the door staff that you’re safely locked away, they’ll make an exception! You can were your best party dress and I’ll show you off to all my friends! Dozens of very gay women, with little use for men in the first place and you’ll have to show them you’re not a threat! I’ll hold your hand and invite everyone to gather round as you humiliate yourself and show us just how far you’ll go in your attempt prove that deserve to have your sex life returned! If had the option, you’d never leave chastity, your cock only for wetting yourself and when we milk you twice a year!”
I shuddered as Ms. Prendergast made me feel like a loser. She asked Auntie Gemma, if I could attend a social function her 1 evening. She asked her where I would be going and she explained that she’d love to take me clubbing and have me fill my diapers in front of dozens of her lesbian friends before changing me right there and then. Auntie laughed and said it sounded like fun and she’d be happy to let me spend the night in another woman’s company, as long as I promised to behave. She said that if I disobeyed her or any of her friends, she should feel free to discipline on the spot. Look just how much I’d been made to suffer when I’d been smacked in front of the 4 of them earlier and a caning wouldn’t go amiss either. Mommy entered my room and looked at me with derision, my p*o covered bottom still being cleaned. She asked Auntie if I deserved to be punished for messing myself and with a very serious face she look through my legs and told me she was very sorry but I needed to be punished for my disgusting behaviour while we had company.
“Nothing less than a juicy dozen strokes of the cane, will do and I’m loathe to give her the satisfaction of my cane for the second time today, perhaps 1 of our guests could be prevailed on to meet out a strict punishment! Even better, why don’t you both cane him, 1 on each side stroking 1 buttock at a time! Such a well-deserved punishment should include a little bondage as well, so we’ll tie the sissy spread eagled and completely naked form the waist down! A nice double caning for such a naughty sissy!”
I looked at Auntie in horror, but she just smiled and carried on with cleaning my dirty bottom. Mommy asked Jenny and Ms. Prendergast to follow her. I was alone with my Auntie and she laughed. She told me that she’d slipped an industrial strength laxative into my milk earlier and I’d had no hope of resisting its effects. I was undone again, but she told me to cheer up and get ready for a double caning. I shuddered as she slid a baby wipe into my crack and told me to stop being such an anal slut. I was shocked by her accusation, but she scoffed at my denial, pointing out that I’d almost fainted when she milked me this afternoon and every time she fingered my bottom I almost melted on her hand. She frigged my bum and I shuddered like a virgin taking cock for the first time. She pronounced me clean, stood me up and told me it was time for my caning. She lifted my petticoat and tutted at the sight of my cock. She picked up my dirty plastic panties, with the duck on the front and had me step into them telling me that I should thank her for her kindness.
I curtsied and she took my cock pacifier out with a plop. I begged her to allow me to visit the lesbian club with Ms. Prendergast and humiliate myself for her, but would she please attend as well, as I would love for her to watch as I’m taken to task by a very cruel woman. I explained that she was a dominant lesbian and had several slaves, if she could watch me humiliated by the most submissive of women, I’d be overjoyed. She smiled and told me she love to see me used that way. Auntie Gemma took hold of my reins and led me down to Mommy’s bedroom where 3 ladies were waiting for me. Mommy looked regal as she took me from Auntie and pointed to her bed. She used 4 pairs of her dirty tights and tied me face down, my plastic pantie covered bottom peeking from under my petticoat. Mommy tugged them down to my knees and lifted my dress and petticoat out of the way. Ms. Prendergast stood on my left, Jenny on my right, both of them in just there lingerie and I could see a damp patch on each of their panties. Mommy rubbed my bottom possessively.
“Time for a much needed punishment sissy and I’ll feel much better when you’re caned by these 2 women! An hour ago, they had no clue as to just how perverted you are, but after filled up your diaper in front of them, they need to give you a very hard punishment! Ms. Prendergast will cane your left buttock and Jenny your right, they’ll each give you a dozen strokes and I expect you to thank them for each strike! Fail to do it and we’ll start from the beginning! Now they have both agreed that you should have the distinction of seeing them in their lingerie, during your punishment, but don’t get any ideas, they just want you to pay for your naughty accident upstairs! Feel free to cry and blubber, after all you’re an utter cry-baby, aren’t you?”
Each of my ladies came into view and I waited for the first stroke to land. Jenny hit so hard started crying immediately. I thanked here and spied her free hand inside her panties. She was openly masturbating and she wasn’t the only 1. Ms. Prendergast was panting as she caned me and masturbated. I looked back and Mommy was watching my beating with a smile on her face and hand in her panties. My spirit’s soured as I understood that my pain and humiliation was exciting them sexually and I was mesmerized by the thought. I thanked each stroke, but I never took my eyes from Jenny’s masturbation. I was balling my lungs out, my nose was running and my bum was on fire, but at that moment I longed for more. More strokes of the cane, more humiliations, more mind games and more teasing at the hands of Mommy, Auntie Gemma, Jenny and Ms. Prendergast.
The final stroke landed and screamed that I needed my potty. Auntie scrambled for my portable toilet while Mommy cut me loose and warned me to not spill a single drop of my nasty stuff on her floor. I was sweating buckets, but Auntie came to my rescue bringing my potty just in time and lifting my petticoat out of the way so everyone could watch my shameful evacuation. All 3 of my masturbating women continued their work, as Auntie held my hand and nibbled on my neck. She seemed to be teasing me, when she told me that I was in need of a real punishment later and asked her what she meant. With a straight face she asked me if I would like to go for a stroll later, she’d love for me to feel the breeze up my dress and the chance that I’d lose control outside and she’d have to change my diaper outside was driving her wild. I looked her in the eye and told yes, that I’d do anything she asked of me. I told her that I wanted her to move in to my home as soon as possible, so that she could make me into her perfect little sissy girl.
“The first thing I want to have you doing, is some very public humiliation! I’m talking long drives into the country for pub lunches, you dressed like a little sissy girl and a very visible diaper on you bottom! We’ll tip the owner a couple of hundred quid and I’ll very publicly destroy you! I’ll bring along a high chair and a big bib and feed you with very messy food, have the waitresses watch you fill your diaper and just when the pong, becomes too strong, I’ll announce in a very loud voice that you need a diaper change! No way will you be able to hide just what a pervert you are and I’ll love every moment of your shame! Or we could go shopping for lingerie together, at small exclusive boutiques or maybe bridal stores! While I’m trying on designer lingerie, I’ll leave you with which shop assistant will take you and I’ll give you plenty of laxatives right before, Chrissy! You’ll have no choice but to fill your diapers in front of complete strangers and I won’t be there anymore because I’ll sneak out and leave you to fend for yourself! I leave you with a diaper bag and you’ll have to pray that someone changes your smelly bum because I won’t return to collect you for an hour! An hour at the mercy of stranger, you’ll be in heaven won’t you and I’ll have you tell me all about your adventure while I masturbate!”
I was quietly sobbing, as I imagined becoming this kinky and inventive young woman’s plaything. She pointed at Jenny’s thrusting hand and asked me if I’d ever imagined that my pretty blonde step-sister would be standing front of me, in her lingerie, masturbating over my humiliating acts and knowing that I was unable join in. I begged her to please keep me in chastity, if it meant she would continue my much needed humiliation and babifacation. I told her that I wished that I could have her smiling face look at me through my legs, as she wipes my dirty bum and puts me in super soft diapers.
In a matter of moments, all 3 women orgasmed in front of me and I was whisked away by Auntie Gemma, to empty my potty and dress me in fresh diapers and new dress and lingerie. My massive diaper was covered by plain opaque plastic panties and over them were sheer white tights, with sparkly stars. A bright pink tutu was around my waist and shiny pink top completed my ballerina costume. Auntie passed my some shoes and I begged her to pick something easier to walk in. Shiny black patent leather, they had 8” heels and were designed to make my weight rest on my tip toes. They are called ballet shoes and were horribly painful foe prolonged use. Auntie told me that she required that I be her pretty sissy ballerina for an evening stroll together.
She sent me downstairs, while she covered her lack of clothes up. Mommy was chatting to Jenny when I arrived and she excused herself and pulled into a big hug. Smiling she pointed to the floor in front of her and ordered me to lick her shoes. I obeyed with delight as I served my step-sister, as a submissive sissy. When Auntie Gemma joined us, a log leather coat covering her lingerie and strap on cock, she asked Jenny to stay in touch with her. Gushing that she’d love to, she asked my Auntie if she ever needed a babysitter for her sissy step-brother she was available. I looked up at Jenny as I licked shoes and she offered to make me suffer for my past misdeeds towards her. I kissed the tips of her shoes
It was Wednesday and Auntie Gemma was moving in with me today. I’d spent the last few days getting everything ready for her arrival and I hoped I’d got everything perfect for her. I’d spent nearly £100000 on clothes, lingerie, specialist furniture and hundreds of accessories. I stood in my porch, waiting and I wasn’t disappointed when she arrived. Dressed in tiny denim shorts a gold bikini top and 5”strappy high heels, she was simply stunning. I dropped to my knees and kissed her feet in greeting, she pulled me up and told me to fetch the rest of her things.
I carried Auntie Gemma’s belonging’s upstairs and put them in the master suite. Since she’d agreed to take on a very much fulltime approach to our relationship, I wanted to show her that she ran the house and I was her servant. I heard her come up behind me and check my diaper under my loose tracksuit. She sniffed my bottom and declared my clean and dry. I thanked her for agreeing to such a strange job offer and pointed inside. She gasped at the room and when I told her that it was hers now she gave a great big hug, her large breasts pushing against my chest. I opened the changing room and watched her eyes pop out when she saw all the designer clothes and lingerie, I’d bought her.
“Someone’s angling for sissy of the year, but don’t imagine you can buy me off, Chrissy, I’m not going to let you off a single humiliating act and when I see you red-faced and crying like a little girl I know I’ve done my job! Now I want you out of that horrible tracksuit right now and into a baby dress and petticoats! No more waiting sissy, I’m going to dress you like a fairy and then give you a nice long hard spanking, followed by an enema and an outing this afternoon! There’s plenty to do, but show me your nursery this instant!”
I headed deeper in to the house, pulling off my tracksuit, till I was dressed in some pink pull up diapers. Auntie tutted and asked me why on earth I would ever wear such horrible diapers in her presence. I explained that when I needed to pass as an adult male, for business and personal reasons, I needed a diaper I could wear under male clothing and not appear out of place. Auntie told me that my excuses were pathetic and she wouldn’t stand for such laddish behaviour. I would wear at least 2 cloth diapers and very crinkly plastic panties from now on. I was hers and I asked her to forgive me. She chuckled and told me that I’d be punished soon. I opened a set of double doors and led my Auntie in to my nursery.
I’d had it designed as the ultimate fantasy nursery and every inch of space was packed with my special items that my Auntie would use to tease and humiliate me. She spent about 20 minutes exploring the space before she told me to strip. I blushed and obeyed her sensuous command. She looked me up and down, her gaze hawk like. She asked me if I had ordered any uniforms for her and I pointed to a door across from the entrance. She told me to set out a selection of diapers, plastic panties and supplies for her to use. I waited for about 10 minutes after I completed her orders and I wasn’t disappointed. She’d picked a very tight satin Nanny Costume, black silk stockings and black 6” patent leather shoes. She’d applied a bright red lipstick and lots of perfume. She winked at me and in a stern voice told me that Nanny would soon have her ickle sissy in some super soft diapers, but she didn’t tell me that she’d have me in pain so soon. She grabbed me by my right ear, twisted and dragged me over to my changing table.
“Nanny is very cross with your naughtiness this morning and I’ll have you in a sissy dress very quickly, Chrissy! No more waiting let’s diaper you and hide your pathetic cock deep inside a super soft diaper! A big wetter like you needs more than 1 diaper, so I think you should have 3 diapers today, they’ll be massive and I bet you’ll be on display for me! How about these plastic panties, blue for a boy, isn’t it but with this amount of frills on the behind they scream sissy! Spread your legs and I’ll powder you bottom, I love the smell of baby powder, don’t you? It’s so sexy and when I rub it into a sissy’s crack, he’s mine to control! You belong to me, don’t you Chrissy? You’d do anything I wanted, take any punishment, any humiliation and all because I diaper this girly bottom! Lift up your bottom and let’s pin you in your soft sissy prison, they’re so nice aren’t they and let’s pin them on! Powerpuff girl diaper pins and some plastic panties to keep all the smelly stuff inside! There we go, Nanny’s diapered herself a sissy baby and I bet you’d love a nice dress to wear now, so let’s go and pick you 1 out!”
Nanny took my hand and I asked her to find me a really girly dress. She smiled at me asked me why. I lisped that I would like to show her just what a pervert I can be and would she please make me sorry I’d ever been born. She giggled and at my earnest response but, told me to be quiet, it was time for her to pick my dress. Literally hundreds of dresses hung against a long wall and Nanny whistled at the choice. Asked me if I should wear a party dress or something much more juvenile, I whimpered that I’d look much better as her little baby girl she nodded and pulled a pale blue silk sailor dress from the rack. Edged in shocking pink lace, I would be Nanny’s to own. She pulled the dress over my head and pulled my arms through the massive pink lacy sleeves. She buttoned me in and placed a shocking pink sailor’s cap on my head. She asked if I needed a petticoat with this dress and in a hoarse whisper I begged her to petticoat me.
“Well if you’re sure, let’s find you a lovely lacy petticoat and make Chrissy the sissy sailor walk the plank! This is perfect for this dress, very fully white lace with lots of pretty pink bows or how about this one, it’s very stiff and will really lift up your skirt and show off those lovely diapers? Oh let’s not decide between them. How about both of them together and you’ll have twice the fun! First petticoat of the day and its very pink, isn’t? Pink’s a very girly colour, but let’s really make you stand out from the crowd; a prissy second petticoat and you’ll be in heaven! Wow that’s lovely isn’t it, the first 1 is very sexy, but the second lifts up you skirt horizontally! No hope of disguising what you’ve got on is there, diapered, petticoated and wearing your dress, let’s find you some socks and shoes!”
We walked over to a large pink chest of draws, filled with tights, stockings and little girl socks. Nanny choose a pair of knee high pink silk socks, that had a large blue ribbon at the top, she tied them into a big floppy bows and I asked her for some pretty shoes. A large collection was next to where she stood and she reached down and passed me a pair of pale blue patent leather Mary Jane’s with 2” heel. She asked me if I needed any make-up and I begged her for some glitter lip gloss, telling me that my wish was her command she sat me down at my massive vanity table, coated my lips with masses of sticky lip gloss before spraying me with a bottle of Nursery Nights perfume. It smelt of baby oil, powder and a very strong flowery overtone. I looked so sissy and I asked my Nanny if I could have a very hard spanking for being such a total sissy. She smiled at me and nodded that I was clearly begging to be spanked. She pulled me towards a high backed chair and d****d me over her lap.
I was to be spanked by my Nanny and begged her to make cry like a girl. She rubbed the backs of my legs, teasing her hand inside my diaper and back out over and over again, till I sobbed that I couldn’t take anymore. She asked me if I was sure because she was going to really hurt me, for my own good and her enjoyment. I begged her to spank me and she became all business, in moments my diaper and panties were around my ankles and she had total access to my bottom. I was at her mercy and she knew it. I felt raise her arm and tensed myself, but she was playing games with me and instead of a hard spank, she rubbed her fingers in to my bum. She tickled the puckered hole with the end of her little finger and I writhed on her satin coved lap. It took me a little while to notice but after a few minutes I was completely sure. In a hoarse whisper I asked her if she was wearing anything under her dress.
“Only stockings, Chrissy, otherwise I’m naked and loving it! Take a look at my legs sissy! My pussy juice is running down my legs! I’m so horny, sissy and I need a big thick cock inside me, but as you no longer have a cock, I’ll just have to take out my frustration on your bottom instead! Let’s begin, shall we, now feel free to cry and kick your legs as much as you like but I’m going to spank you 150 times this morning, very hard and very quickly! So much for being my sissy sailor, in a minute bawling like a naughty little girl and I’ll be so very impressed with you! Most women want big strong strapping men, but I love fem boys who’ll dress in lingerie and suck cock, even when they mess there diapers! You’re my perfect man; well I use the term very loosely!”
With no warning she laid into my bottom raining down smack after smack. I tried to escape her terrible rhythm, but she dragged me back to the centre of her lap and started on the backs of my thighs. Right where my buttocks ended and my legs began. I pleaded with her to stop, but she laughed at me and increased her pace. I was her sissy and she revelled in my submission to her. I screamed and blubbered, but she ignored all my cries for pity. When she stopped, she breathily asked me if I’d enjoyed my punishment as much as she had. I looked at her with incredulity and she kissed me on the lips, darted her tongue into mouth for a moment and stroked my cheek tenderly.
She told me that I’d been very brave and she’d been impressed with how well I’d taken her spanking, but I could expect nothing else, as she was sure that I would be next to useless without strict and severe chastisement. I asked her if she really thought I was brave and she giggled at my question, telling me that I was a very brave sailor and it was her job to make me into the best sissy anyone had ever seen. She asked me if I’d fuck her, as she needed a jolly big cock in her pussy, right this minute. I begged her to unlock my chastity and I’d do my best to give her a right good seeing to.
“I didn’t mean that, Chrissy! That would be disgusting, your cock is only good for wetting your diapers now and you should accept that you’re never getting out of chastity! If I fix your diapers and plastic panties, I could put a nice big strap-on over your diapers and you can pretend to be a real man! Would you like to fuck your Auntie, Chrissy? You’ll be locked safely in your diapers, but I’ll have the satisfaction of a thick cock inside of me and you’ll be able to fuck like you’ve always wanted to! You could bend me over this chair, lift up my dress and do me from behind! I need you to be a good sissy for Auntie and do as I ask! Please!”
I was horrified at the thought of this latest assault to my last remaining sense of manhood, but Auntie Gemma looked at me with such a little girl pout, I couldn’t say no to her bizarre request. When I told her that I’d do it, she gave me a great big hug and said I was her favourite sissy baby. She pinned me into my diapers and pulled up my plastic panties, telling me that she’d give me a big cock, to wear over my diapers and I could pretend it was my real cock. With a squeeze of my arm she guided my over to a packed shelf, with dozens of sex toys, lube and a selection of strap-on. She asked me to choose which of the cock’s would be inside her pussy and told me that bigger was definatly better. I looked at the choices and spotted a large pink strap-on, even the belt was pink and I pointed to my choice.
“A pink strap-on for my sissy sailor to fuck his Auntie with, it’s perfect and it’s very big, but is it thick enough? I’ve had a lot of cock and I’ve got a very well used pussy, so I better check! Give it to me and I’ll just have a quick try! Would you be a dear and lift up my skirt, Chrissy? Your being so good today, I’ll have to give you a very special treat later and have you show me just what lingerie you’ve bought me! Oh that’s nice and thick! You’ll be able to fill my pussy and give me a proper fuck! Let’s get some lube and you’ll be ready to make me orgasm!”
She was smiling as she had me step into the pink strap-on and tightened the belt. She lifted my petticoat out of the way and asked me if that cock was hard for her. I nodded and smiled, took my hand, guiding me back to her spanking chair and bent over the seat. She pulled her dress over her waist and her soaking pussy was right there, waiting for my cock. She looked back at me and begged me to stick my pink cock in her pussy and fuck her. I smiled as I realised that for once I had the power and asked her if she’d ever been fucked by a sailor before. She giggled and told me she’d been spit roasted by 2 Marines, but I was her first sailor. I told her she was dirty slut and that I would soon be deep inside her sopping wet pussy.
I lubed my cock, positioned myself behind Auntie Gemma, grabbed her hips and pulled her onto my hard cock. She grunted, as I sank myself deep inside of my strict mistress and asked her if I could be allowed the honour of fucking her. She looked back and told me to shut up and do it. I began to build up a rhythm and forced myself into her. Faster and faster, I fucked my Auntie. She was like a wild thing as we made love, in the only way possible for a chastity wearing sissy and I begged her to take me like this. She was angry at my interruption, telling me that I was her sissy and she would decide when I would lose my anal cherry. She promised to use this strap-on when she did fuck me and I would understand just how big it was. I pounded away, until Auntie Gemma screamed in orgasm and sank to the floor in front of me. She looked up at me and reached up, took my cock in her hand and put it into her mouth. She gave me a pretend blow-job, licking her pussy juice from my cock and deep throating it.
“You’re such a naughty, sissy aren’t you? Fucking your Auntie and pretending to be a real man, but don’t forget that your cock is locked away in diapers, like a sissy should be! Your nothing more than a convenience, I could have just masturbated, but I allowed you the illusion of fucking me! Now let’s have you in your proper position, on your knees and licking my shoes! That’s better, you love the taste of my dirty shoes, but don’t forget the stiletto’s, sissy! Suck them, go on suck my stiletto’s and I’ll give you a very nice lunch! I spotted a lovely high chair and some baby food in the kitchen earlier! Auntie will strap you in and feed her little sissy baby, give you as many bottles of lovely milk as you can drink and burp you! I’m going to fill you with lots of very soft baby food and watch you try not do a very big p*o-p*o in your diapers!”
I looked at her with wide eyes and in a simpering voice asked if I could be breastfeed like a real baby. She told me not to ridiculous, she wasn’t lactating and expected me not be silly. I told her that I’d bought a very naughty apron, with holders at the right place and she could secure 2 baby bottles in the holes. She laughed and ordered me to show her. The apron was hanging on a hook beside my crib and I pointed to it. Auntie Gemma grabbed it and held it up. Made of shiny white latex and knee length, it had the phrase “Dinner Time” on the front. She put it on and looked at me with a very stern expression. She asked me if I was k**ding, because if I wanted her to use this for my feeding, I would have to be very good and do something nasty in my diapers. I begged her to wear it and I promised to do anything she asked.
She told me to go and prepare 2 bottles of formula, while she set up an enema kit. I was red- faced, as she told me I would have to fill my diapers with contents of a nice soapy enema, to be treated to such a kinky lunch. She told me to hurry up and she’d be ready in 10 minutes. I headed to my kitchen, my behind waddling from the extra-large diapers I wore and prepared my lunch. When I returned, Auntie Gemma was grinning like a Cheshire cat and dragged me to a medical table, with stirrups at the end and straps to tie me down. She removed my diapers and plastic panties, telling me that she needed unrestricted access to my bottom. She sat me down and strapped me in, putting my feet in the stirrup’s and asked me if would like a pacifier to suck on. I nodded my head and she produced a cock pacifier for my mouth, tying around my neck.
“It’s time baby’s first enema and I’m going to fill both your holes with cock! Look at the nice dildo that came with the kit, it’s very big and it will fill your bum to bursting, but I want you to take it like a good girl! The trick is plenty of lube and steady pressure, but don’t worry if it doesn’t feel like it’ll fit because all sissy’s bums can take real big cocks! Now let’s see if you’re ready, is your bum lubed and all slippery? Yes it is! Are your leg’s spread and open? Yes they are! Time for Chrissy’s first enema then!”
Auntie Gemma tickled my hole with the slippery tip, teasing me outrageously and made me blush like a little girl. She knew me so well and I longed for her to use me like a dirty little girl. She tickled my balls, stroking them and asked me if wanted her to milk my prostate with her big dildo. I nodded and she smiled, telling me that I had no choice and she would make me dribble all over my enema table. She was teasing me, making me shudder at her touch, as looked at her beautiful face. Auntie Gemma leaned in close to my crotch and blew on my chastity covered cock before taking the plastic into her mouth and sucking on it. I was being given oral, as she slowly pushed that dildo inside me and moaned like a slut. She was overloading my senses and I couldn’t take it. She pulled away and licked her lips.
“You taste like baby oil and stale pee, sissy! It’s lovely, but I don’t want you to imagine that I’ll be sucking your cock again, well maybe if you open up completely and take my dildo! You need to understand that I expect you to obey me and when you don’t I’ll have to punish you harshly, but you already know that don’t you? You belong to me now and I’ll treat you as I see fit! Your bottom is mine to fill, with cock, my fingers and warm soapy water, so don’t resist my demands, Chrissy! Take every inch and I’ll put your cock in my mouth, lick your chastity and make you feel so good! That’s better it’s almost in, just another inch and you’ll be totally filled! I’ll just pull it out, very slowly and push it back in! I’m fucking your bum, sissy and you love it don’t you? Auntie’s little baby girl is such an anal slut and you can be sure that I’ll do this every day, strap you down and fuck your bum!”
I was bright red, sweat dripping, as moaned into pacifier and took her cock. She spanked my bottom and blew on my cock, all the time fucking me deeper and deeper. She was in complete control of me and I needed to spurt. She pulled her dildo from my bum, suddenly, with a plop and slapped my very hard. She strode to my side and untied my pacifier, pulling it from my mouth. She told me that I wasn’t trying hard enough and she was not impressed with efforts. I begged her not to stop and she asked me if I was sure. She was very earnest, as she asked me to be sure that I wanted her cock in my bottom and a nice big enema. I told her that I needed her to finish me off and I was trying my best, but she was making it so difficult do my best when she was teasing my cock. She was not amused and in a cold voice told that she owned my cock and if she wanted to put it in her mouth I had no say.
I asked her to pop my anal cherry and I was very sorry to be so dense. I promised to take every bit of her cock, but I was a virgin and was feeling very scared. In a whisper, I told her that I didn’t want her to think that I was gay and I burst into tears. She laughed at my confession and told me that I was such a silly girl. She knew I wasn’t gay, but I was a sissy and I needed to understand that sissy’s bums were there to be filled. She stroked my face and I looked into her eyes, in total submission, as I told her that I loved her. She just smiled and blurted out that I didn’t expect her to understand, but I was hers. I promised to always put her wishes and desires, ahead of mine and I wanted to show her my commitment.
“You’re so sweet, but I already know just how much you’ll do for me, Chrissy! I mean, just look at what you’re taking in your bottom for your Auntie! Maybe if I tell you that I’ll be bringing back some of my boyfriends to the house, from time to time and I’ll let you help me get ready for my dates! Just think I’ll be taking my boyfriend’s big cocks, while you’ll be waiting at home; diapered, in your crib and imagining everything I’m up to! Don’t worry though, I’ll fill you in on all the sexy details when I get home and we can pretend that it’s a bedtime story! Auntie understands that little sissy girls can’t be left on their own, though, so you’ll have to have a babysitter for the evening! Your step-sister, Jenny, offered and I’m sure she’ll love the chance to renew your relationship!”
The thought of Jenny babysitting me while my Auntie Gemma went out and fucked real men was just what I deserved. I asked her if she would let me pick out her lingerie and clothing for her dates, my face blushing red and she told me that I would have to be very good. I told her that I would be the perfect sissy baby girl for the honour of serving her and could I please be allowed to bathe her for her dates as well. She smiled and said that I was precious. She pushed her cock all the way up my bum, took my chastity covered cock in her mouth and sucked deeply before releasing it. She grinned and said that I needed to be brave, as it was enema time.
She attached a long plastic tube to the hollow cock in my bum. It ran up to a large red bag, hanging from a metal stand and had a tap near the top. She pointed to the bag and told me that she’d be opening the valve in a moment. I sighed and asked her if she would hold my hand while I took my first enema. Auntie Gemma nodded and licked her juicy red lips. She pulled over a white wooden stool, placed it next to the head of my bed and sat down. She took my hand into her well-manicured, delicate fingers and squeezed. She bent down and whispered in my ear.
“Now get ready, this will feel a little weird, but you do want to be a good girl for Auntie, don’t you? I’ll go slowly, just a bit at a time and let you get used to the liquid, but you’re going to take every drop for me! Here goes, sissy’s first enema and Auntie’s so proud of her sissy! That’s it open wide and I’ll fill your bum with lovely warm soapy water! I’ve even added some lovely flowery bath salts that should bubble and pop inside your bottom! You should see the look on your face, it’s a picture of emotions and I love it! There’s nothing better for an Auntie to witness than a mixture of shame, humiliation and desire on the face of her charge! That’s enough for now, Chrissy.”
Auntie Gemma stopped the flow and reached down, gently massaging my swollen belly, making me whimper and beg her not to. She laughed, telling me that she was helping me and I should be grateful for her actions. She explained that she was forcing the liquid deeper, making room for the remainder of the enema and giggled that I was such a pantywaist. Auntie Gemma stroked my face and looked at me so tenderly, her eyes bright and clear. I was lost in her gaze, as she continued her massage and I forgot everything, but her.
She asked me if I was ready for some more and I nodded, her eyes locked on mine. She was pleased, I could tell and she opened the valve once more, took my hand in hers again and lifted my petticoats out of the way. My cock was dripping, like an old tap, my spunk running down my smooth whit thighs and pooling on the waterproof table. She was delighted at the sight and deliberately took my very full balls in her free hand and squeezed them. I shuddered at her touch, her teasing of me was artful and I begged her not to stop. Her grin was ecstatic and she bent over, her hair tickling my shoulders and chest before kissing me on the centre of my forehead, in a loving manner.
“Little sissy’s who milk while taking their enema’s, need to be humiliated and controlled for their own good, don’t they? I’m taking you out after lunch, for an outing at the convention centre in town and you’ll be so empty inside your diapers! No nasty p*o-p*o in your bottom and no nasty spunk in your balls, either! Don’t be scared about everyone seeing you, though, Chrissy because it isn’t going to help 1 little bit! You’ll be on display for all to see and I’ll be eating up every ounce of your humiliation! Just the thought of it is making me wet and we’ll have to nip in to the baby changing room at some point for me to masturbate! Don’t worry though, I’ll be giving you a nice treat as well, I’ll change your wet diaper and let you lick my hand clean afterwards, won’t that be nice?”
I begged her not be so cruel, but she was having none of my cheek and promptly stopped her teasing of my balls. She slapped the insides of my thighs, very hard and told me that I was in no position to expect any kind of special treatment, at her hands and she was in charge. She slapped me hard across the face and screamed at me that I should beg her to humiliate me publically, for her amusement and my shame. She seemed transformed from the caring and gentle young woman, of a few moments ago and I was very frightened. I was at her mercy and I had no one to blame, but myself. With a simpering and apologetic tone, I begged her to shame me publically.
In a second, she turned from strict, severe dominant and in to happy Auntie Gemma once more. She sat down next to me again, turned off the valve and massaged my massively engorged belly. She carried on like nothing had happened, telling me that I was nearly finished with my enema and she would so give me a nice feeding. She giggled and reminded me that I would have the distinct pleasure of suckling from the bottles attached to her apron. She told me that I was very lucky to have such a caring Auntie and not many sissies were as lucky as me. She stroked my face and whispered in my ear.
“Chrissy, I’m going to feed you sitting on my lap, like a good girl, but I want you to know that I expect you to fill you diaper for me, while your Auntie suckles and gives you her milk! You’ll feel so nasty, as I laugh at your messing and I want you to know that I’ll love your submission to me! Imagine filling your diaper, on your Auntie’s lap and humiliating yourself, but that’s what I desire from you! Your cock doesn’t turn me on, but every time I see that look of shame, I melt inside and you do want to please me, don’t you? You do, well then we’ll just have to hurry up then, so open wide and I’ll finish your first enema!”
Auntie Gemma was all business, as my enema was completed and she tidied the equipment away. She was very insistent that I not spill a drop of that liquid, from my bottom or she would take great pleasure in using a very long bull whip on my behind and have me clean up the mess before starting all over again. I was sweating like a teenager buying his first condoms, as Auntie Gemma helped me down, supported me over to my changing table and helped me up. With a practiced ease, I was diapered in 3 pairs of very thick pink cloth diapers with 2 absorbent pads inside and pinned up with 2 pairs of blue bunny rabbit pins. Auntie Gemma added a set of massive clear plastic panties and finished off by replacing my blue frilly panties over the top.
She helped me up and together we waddled over to a full length mirror. She turned me around, showing me my massively diapered bottom and told me that I’d soon be filling them for her. She kissed me on the lips and caressed my upper thighs, cooing that I was a very naughty sissy and I should be ashamed. She had me stand next to her, as she positioned those 2 formula filled bottles, through the holes and got ready to feed me my lunch. She bought us back to the mirror and asked me if I thought she was beautiful. I nodded my head, my belly gurgling and told her that she was a vision of dominant woman-hood.
Auntie Gemma took my hand, led me over to the high-backed chair and sat down. She guided me on to her satin covered lap, preened my dress and petticoats before asking me if I was hungry. I told her that I was starving and she told me that dinner was served. She lowered my head down, onto the first nipple of her bottle and in a very hoarse voice told me to feed on her milk. I sucked on that teat like a sissy possessed, my eyes glued on hers and my belly straining from all that liquid. I was in sissy baby heaven, as I was allowed to breastfeed, at my Auntie’s pretend breast and she was slowly laughing at my performance.
“What a display, Chrissy and I hope you understand just how pathetic you look right now! You’re a disgrace and I’ll be telling all the ladies we meet, on our outing this afternoon, all about this! You’ll be sure to answer any questions they have about your perversions and I’ll be sure to explain that you need me to inflict them on you because you’re such a dirty little girl! They’ll be plenty of young ladies and more mature women there, as the centre is hosting a wedding dress exhibition! You’ll be surrounded by dozens of stalls, filled with wedding dresses and oodles of sexy lingerie! Just the place for sissy’s first outing and I’ll be extremely happy if you buy me some darling lingerie! If you pick out lots of very expensive lingerie for me, maybe we could have a fashion show when we get home, eh? I’ll parade and model every piece, while you watch and suck on a lovely penis pacifier! Auntie Gemma will even let you pick up and put every item in her lingerie draws, like a good girl! Such a nice treat, for such a naughty girl, but I’m happy for you to show my lingerie the respect it deserves and don’t pretend you won’t love it!”
I was in shock, as Auntie Gemma verbally teased me and I was unable to answer her, as I sucked on her full breast. She cooed and gently eased my mouth of her first bottle, lifted my face and licked a drop of milk off my chin. She clearly loved my degradation, but she reminded me that I had forgotten to do something and I should stop stalling. She laughed, her voice light and sexy, telling me that I would have to mess my diapers, if I wanted her other bottle. I tried to explain that I was embarrassed, but Auntie Gemma was not impressed and told me that I had promised to humiliate myself for the right to drink her milk and I had better fulfil my pledge. She looked at me with real intensity, her face inches from mine and licked her lips in anticipation. She obviously wanted to take in every moment of my embarrassing action and I just let go of every part of my ego.
I farted, loudly and emptied my enema filled bottom into my diapers. I was crying, as Auntie Gemma laughed in my mortified face and I was so ashamed. Her I was, a 40 year old man, dressed as a little girl and I was filling my diaper on a beautiful woman’s lap, like a baby and she was amused by it. Auntie Gemma lowered my head down onto her other bottle and I took solace in the activity, as she was making me her total sissy baby girl. I was unable to stop crying as Auntie Gemma had me drink down every drop of her milk, all the while she was softly laughing and caressing my legs. She stood me up, took my hand and led me over to that damn full length mirror.
“Well that was a very pleasant feeding time, don’t you think, Chrissy? I was a little hesitant about feeding you this way, but it was very erotic for me and I look forward to making it a more common practice! There is 1 thing I have to ask you though and I hope you don’t take it the wrong way, but can you smell p*o-p*o? I’ll just check your diapers and make sure! Well, they’re absolutely brimming and I’m so happy that you felt comfortable enough to use them in my presence! You must want to show me just how much you belong in diapers, if you’re capable of messing whilst sitting on my lap and I’m delighted with your progress! Do you want to see your messy diaper, well turn around, bend over and I’ll lift your petticoats out of the way and you can inspect them!”
I was helped in to position and as I looked into that mirror, I truly began to appreciate the mess I’d filled my diapers with. They had started out as the largest set of diapers that I’d ever worn, but now they were almost twice as big. In fact I was surprised that they were able to handle the load. Auntie Gemma was rubbing my bottom possessively, her hand a sign of her utter ownership of me and I was made to feel like a real baby, as she told me that she would be changing me in a few moments. She asked me where my bathroom was and I pointed to a door across the room. She headed straight for it and told me to join her in a few minutes, after I spent the time experiencing just what I’d done and what I would be doing in my diapers from now on.
I was left alone, standing in front of a mirror, my dress and petticoats up with my full diapers on display. I stood up turned around and lifted my petticoat out of the way, to take in the sight of my full diapers from the front. I was so ashamed at what I’d done, I was still crying at my reflection, but I had been in denial about my desires for so long and now there was no escaping the truth. I was a sissy baby girl. I couldn’t believe just how ridiculous I looked right now, but I felt myself becoming turned on and I wasn’t ready for it. Not many people become aroused at the feeling of messing there diapers, but I was obviously 1 of them and I needed my Auntie Gemma right now.
I waddled across the room, the smell of my diaper following me and entered my specially set up bathroom. The whole room was tiled with large white tiles and fitted with shiny stainless steel equipment. There was no toilet, no shower, just a large bath, a massive double sluice sink and large waist high changing station. It looked like something you’d find in a N.H.S. hospital and was completely water-proof. Auntie Gemma was sitting on the edge of my bath, hot water and bubbles slowly filling it with her dress up around her waist and her hand inside her pussy. She looked at me through hooded eyes and told me to stand in front of her. Auntie Gemma told me that I had made her wet and she intended to masturbate, as she took in the sight of me with a full diaper and that I should thank her.
I thanked her, my voice cracking with tears and begged her to please allow me to tell her something very rude. She nodded at me, her face red with arousal, as she continued to play with herself and I had better hurry up. I told Auntie Gemma, with a sense of utter surrender, that my dirty diaper was making me horny and would she please punish me for such lewd behaviour. She smiled and told me that I was a disgrace that I was unfit to be in the presence of a woman like her and I deserved to be caned for my admission. She looked at me with scorn and told me that I was a pervert in need of correction, but that I was to wait until she had finished her wank.
“Do you understand why Mommy took the step of locking your cock away, for good, now Chrissy and why I intend to very publically humiliate you? A real man doesn’t become aroused when he has an accident, a real man doesn’t rush to tell the nearest pretty girl about it and a real man doesn’t cry as he’s told off, by his Auntie! In fact, I’m going to tell your step-sister, Jenny all about this latest disgraceful admission right now! Does that phone on the wall work? Good, put it on speaker phone and dial Jenny at home, this instant! Don’t pretend that you do not love every minute of this, sissy, but I know just what will really make you cry for me and having Jenny know about this is just the ticket! Now, sissy! I’ll carry on wanking; while I tell Jenny and you can listen in!”
I called Jenny’s home number, praying that she was out and when it reached the 8th ring, I started to breath more easily, but I was out of luck today. My step-sister answered her voice cheerful and asked who was calling. Auntie Gemma told her that both she and her nasty step-brother were on the line, her voice rough from her excitement. Jenny was thrilled to hear from Auntie Gemma and asked if she wanted her to babysit, but I wasn’t allowed to let her finish, as I was instructed to explain just how I was dressed and what I’d done in my very smelly diaper. I was sobbing, as related my condition to a very attentive listener and told just what I’d been up to this morning,
Jenny seemed very happy to hear all about my experiences, at the hands of my Auntie, but when she hissed at me to tell her what I’d just admitted to her, I was reluctant and begged not to be made to tell. Jenny asked me if it was very naughty and I told her that I was so ashamed, but please would she not make me tell. Jenny laughed and in a very matter of fact tone, informed me that I was to be totally honest or when she babysat me for the first time, she would bring several of her friends with her. Auntie Gemma grinned and told her to go ahead, I’d be delighted to meet some new ladies who could embarrass me and maybe even change my diaper. I looked at her with horror, but she grinned and told me that I better explain right this minute or she’d ask Jenny to arrange an Ann Summers party for 20 of her closest friends and I’d be the evening’s entertainment. With a very tearful voice, I told my step-sister that my dirty diaper was turning me on and I had just told my auntie all about it.
“That is a very naughty and rude thing to tell your Auntie, Chrissy, but I’m sure that it’s normal for nasty sissy baby girl’s, who have their cocks locked away in chastity, to be aroused by their dirty diapers, because they want to be wicked and ashamed! In fact, I bet you’ve been dripping your unclean spunk, in to your diaper all morning and I’m disgusted by attitude! When I’m in your presence next, I’ll cane your bottom for dribbling and don’t think I’ll go easy because I’m your step-sister! I’m outraged at your demeanour and I mean to correct it very quickly! Now then, I’ll be going, as I need to masturbate, rather badly, after hearing about your first morning and you don’t need to listen in! Gemma, call me to set up a time and I’ll be delighted to help out!”
With a click, Jenny rang off and left me staring at my Auntie. She told me that I was making it very difficult for ordinary ladies to stop themselves from masturbating, at the sight and explanation of my total humiliation. I was ordered on to my knees, my diaper straining under the pressure and to lick my Auntie’s stiletto heels. My submissive act was the final straw in Auntie Gemma’s dam and her orgasm exploded right in front of me. I continued my directive, until she recovered and pulled me to my feet, telling me that she would be changing my smelly diapers now. Firstly she helped me out of all of my clothing, except for my sailor’s hat and my diapers and plastic panties.
She stood me over a large potty, made of clear plastic and decorated with a white prancing unicorn on the front. She told me to squat and get ready. Auntie Gemma pulled on elbow length latex gloves, the kind a nurse might wear and a white rubber nurse’s mask, a big red cross on the front. She giggled at me and told me that I had been very naughty, but she would change my diaper because she wanted me to be nice and clean for our outing later. With a swift pull, Auntie Gemma tugged down my plastic panties and diaper. There was a loud plop and a horrible smell, as enema emptied into that potty. With a sense of glee, I was verbally humiliated once again and I sobbed at my shameful state.
“Well that’s a very full diaper you were wearing, Chrissy! Can I expect future occurrences to be as satisfying for me and totally humiliating for you? Ohh, you looked so mincing in your little sailor suit, earlier, but a nice juicy enema, followed by a disgusting mess in your diaper and your putty in my hands, aren’t you? Now I expect your best behaviour when we go out later and any resistance to my instructions will be punished by 3 additional enemas, when we return home! Now there’s no use in trying to pretend that you didn’t expect this, is there? You bought all of these wonderful toys and clothes for us to use and when you accept that fact you’ll stop crying! Now, step out of your messy diapers and I’ll rinse you down with some water! You thought ahead when you made this a wet room and all the nasty p*o-p*o coming off your bottom will go straight down this drain in the floor! For that brilliant idea, you can suck on your penis pacifier and I’ll clean you up!”
I was hosed; baby wiped and inspected until Auntie Gemma was satisfied before she lowered me into the waiting bubble bath. She removed my sailor hat before pulling a large opaque pink rubber bathing hat onto my head, protecting my wig and proceeded with a very intimate baby bath. Auntie Gemma was relentless, she scrubbed every inch of me with a very soapy flannel, paying particular attention to my chastity covered cock and balls. She hummed a tune, under her breath, as she flipped me up onto all fours and cleaned my bottom. She squirted a large dollop of Johnson’s baby bath on to her latex covered fingers and gave me a deep cleaning of my bum.
I moaned, as I sucked my penis shaped pacifier, while I was fingered by my Auntie and she gave no sign of noticing. When she added a second finger, I whimpered and she tutted me, telling me that I’d had much bigger things inside me earlier and that I shouldn’t complain now. I was expertly teased by that happy young woman and when she finished, I was barely able to obey her order to step out of the tub. I was handed a large My Little Pony towel and instructed to dry myself, as she needed to clean up some mess. Auntie Gemma emptied my potty, down the sluice sink and washed it clean, leaving it to dry on the side. She then pulled a mop and bucket from a cupboard, filled with hot water and bleach and handed it to me.
I was ordered, naked for shame, to mop up the mess my enema filled diaper had made on the floor and then empty the bucket before putting it away. When I was finished, Auntie Gemma passed me my potty and ordered to inspect it. I told her it was spotless and she grinned, telling me that if I was so sure, that I wouldn’t mind licking the inside and making sure. I looked at her in outright horror. She wasn’t joking and I was made to kneel in front of her, look her in the eye and beg her for permission to lick my potty. She laughed.
“What a depraved thing to beg your Auntie to do! I’m flabbergasted that a sissy baby girl, under my supervision, would ever be so shameful in her desires, but who am I to stop your nasty tongue entering your potty and licking it! I expect you to do a perfect job, Chrissy, every inch covered and no shirking! Go on, I’m watching and don’t think I don’t understand your perversions, sissy! Your Mommy will want to be told about this and I expect you to demonstrate for her when you next meet! What a naughty sissy!”
I was without a frame of reference, as Auntie Gemma turned everything that she ordered me to do, back on to me and made it seem as though I was the 1 who wanted to do these humiliating things. As I licked my potty, my strict tormentress, looked down at me with delight, as she was witness to my cleaning and I wished for her to give me a chance to recover. She declared me finished, took away my potty and pulled back out in to my nursery. She dragged me to my changing table and I was dragged up before she tickled my balls. I was incredibly horny, but the only release I’d been allowed since I’d been locked in chastity was a milking and I needed a spurt. Auntie Gemma knew this and continued her teasing of my balls.
She asked me if I would like the option of being allowed a very special treat on either my birthday or Christmas. I sucked on my pacifier and looked at her quizzically. She told me that she’d spoken to my Mommy and between them; they’d decided that once a year I’d be released from chastity and under strict supervision, I could masturbate to orgasm. I moaned at her announcement, but as ever there was a catch. I would have to get the approval of all 3 of my guardians, namely Mommy, Auntie Gemma and Jenny. If 1 of them disapproved, I’d continue my chastity regime for another year and have another 365 days without spurting.
Auntie Gemma poured baby oil onto her hands and lifted my ankles up before pushing them back around my ears. My bottom was exposed and I was soon violated by a slippery middle finger. I was told that if I agreed to my birthday, which was only 2 months away, she’d take great pleasure in having me masturbate into a pair of her expensive silk panties, but in a very public place. She hadn’t made up her mind, but she thought either the changing rooms of Victoria’s Secret, in the local mall or in the ladies toilet at a male strip club. She smiled and in an offhand comment told me that, I’d be on display either way.
My Mommy on the other hand wanted it to be at Christmas, with her dressed as a very sexy Satan Claus, sitting on her knee, telling her what I wanted and with Jenny dressed as a thigh booted pixie. She’d have an enormous cock strapped around her waist and I’d have to suck it before I was bent over Mommy’s lap and fucked by my step-sister. When I’d been well used and abused, they would dress me in a lovely sissy party dress, a nice girly coat and attach my reins. Within an hour, I’d be at a little fetish club that my Mommy knows and my masturbation would be the highlight of the cabaret show. In front of dozens of strange men and women, both submissive and dominant, I would be un locked and ordered to fill my Mommy’s dirty panties with my spurt.
“You’d have exactly 5 minutes to spurt before we’d lock you away for another year and laugh at your predicament! No hard on’s for so long and then such a short time to perform, in front of everyone and no hope of any privacy! We’re hoping that you’ll say yes to our suggestion and maybe I’ll even let you look up my skirt why’ll you rub, I won’t be wearing panties, Chrissy and I’ll be totally wet for you! Auntie Gemma’s pussy right in front of you and your hard cock in your hands! All we ask is that you buy us each a diamond engagement ring! Don’t look so shocked, I thought you understood that we both like money and the quickest way to get it is through marriage! 1 of us will walk down the aisle and become, in the eyes of the law, your wife, but in truth we’ll continue as your Auntie and Mommy!”
I shivered at Auntie Gemma’s and Mommy’s plans for my future. I looked at Auntie with hunger, as she removed my pacifier and asked me what I thought. I sobbed in pleasure and begged her not to tease me so much, that I knew that neither of the 2 most wonderful women I’d ever met would ever marry a loser like me, even for half of my fortune. Auntie Gemma laughed and explained that nothing would change; they’d be keeping me in diapers, humiliating me for the amusement and having sex with lots of other men instead of me. She pointed out that I was in need of a committed relationship, even such a perverted 1 and they were willing to take control of every aspect of my existence.
Auntie Gemma’s fingers were magic and when she slipped a second inside me, I was unable to resist her. I begged for permission to marry her, promising to love honour and obey her. She laughed and asked about Mommy. I told her that I was forever grateful for Mommy’s discovery of my true nature and for her introduction to her, but I craved her. I was lost inside a world of humiliation and submission that she had created, but I longed to be her's forever and would she please agree to marry me.
“That’s so very nice to her, Chrissy, but I think you’re fibbing to Auntie and you just want to string me along, hoping that I’ll release you from chastity, on our wedding night and you can escape! You won’t, well maybe I’ll say yes, but only if I can have your decision on your birthday or Christmas treat! You pick me, sissy, well that’s very well done and I’ll be planning your surprise between now and then, but I think we should get ready for today’s outing now and it will be extra special now, won’t it? Remember that we’ll be attending a wedding dress designer’s convention today and we can pick out your dress for our big day, can’t we? I won’t need 1, as I’ll be dressed in morning dress, top hat and tails, but I want you in a very big and feminine gown for our wedding! I’ll call Mommy and Jenny, after I get you dressed, as they’ll want to enjoy our news and help with the choices of dress!”
I was in ecstasy, as Auntie Gemma, blabbered on about just what a cute bride I’d be for her and how much she was looking forward to trapping me in a marriage of convenience and getting hold of half of my money. She pulled 2 large white cotton diapers out and placed them next to me, next was a set of 4 pink piggy diaper pins and a pair of opaque pink plastic panties followed. Auntie Gemma powdered my bottom and with a moment of intense desire, diapered my bum. She pinned me tightly inside and followed with the plastic panties. She gently rubbed so more powder between my legs before helping me down and leading me over to the racks of baby dresses. She asked me to pick a very sexy dress just for her and if she liked my choice, I’d be allowed to choose her lingerie and clothing. I asked her if she would allow me the honour of kissing each item of her clothes and she smiled before nodding.
I spent the next few minutes going from dress to dress, but I was drawn to 1 in particular. Made from white bridal silk, with yards of frothy sheer white glass silk forming the sleeves and edged in pale pink lace, I was sure that Auntie Gemma would approve. When I showed her my choice, she asked me if I thought it was girly enough for such an important day and would I be able to make enough of a statement. I told her that I would be utterly humiliated to be seen in public wearing such a sissy little girls dress and with a very stiff petticoat my diapers would be on display. She giggled and agreed, telling me that I’d done well and she would love to see Jenny’s face when she caught sight of me.
I asked Auntie Gemma if she would allow me to pick out an appropriate petticoat as well and smiling she assented. I chose a very stiff lace net petticoat, white and pink like my dress which was covered in pretty pink bows. I asked her if my opaque plastic panties would be able to cope with such a stupendous petticoat and she laughed, telling me that she had some special rhumba panties waiting for me in her room and she’d be pulling them up my legs, over my diapers for everyone to see. I looked at her with such red face that she asked me what was wrong. In a small voice, I told her that I was so much in love with her and wanted nothing more than to please her forever.
“Chrissy, you say the most darling things to your, Auntie, but I want you to be under no illusion about how you please me! The more I humiliate you the wetter I get and the thought of seeing you in this dress, in public and Mommy and Jenny by our sides is like crack to me! I’m an addict and you’re my d**g! So let’s stop lolly gagging, pick out some stockings and a frilly garter belt before I have to masturbate again!”
Auntie Gemma passed me a pair of sheer white silk stockings, with a seam and a pattern of pink roses running up the legs. The garter belt was white silk, dripping with pink lace and had 8 tabs, each of which had a pink rose at the end. She passed me a white and blue bridal garter, dripping with lace and designed to be worn at mid-thigh. A pair of pink cotton little girls socks were next, the tops edged with white lace and ankle high. A pair of simple black patent leather Mary Jane’s, finished off my leg wear before she asked me if I would like a nice baby bonnet to wear.
I nodded and asked her if she would choose a very girly 1, as I wanted my step-sister Jenny to laugh at me and she’d love to see me absolutely humiliated. Auntie Gemma beamed and told me that she’d seen just the thing earlier. She left me standing there for a few moments before returning with a glass silk and lace confection. It was massive, several feet across and made to be noticed. Auntie Gemma asked me if I was sure and red faced, I told her that I would look ridiculous and I hoped that she’d make me feel very ashamed to wear such a frilly bonnet. Auntie Gemma told me to apply lots of perfume, some glitter lip gloss and wait for her return.
A few minutes later, Auntie Gemma stood in front of me, a full bottle of formula in 1 hand and a pair of rhumba panties in the other. She passed me the bottle and told me to drink up while she showed me the panties I would be wearing. Made of sheer pink glass silk, yards of which formed ruffles on the bottom, it was the front that held my gaze and made Auntie smirk. The whole front was see-through, but for the phrase “AUNTIE’S SISSY!” stitched on the front and telling everyone the truth. I was Auntie Gemma’s sissy.
“Now then girly, let’s have you dressed for your outing and we’ll start with these delightful rhumba panties! I had them made especially for this day, when you became my bride to be and understood just what it entails, lots of public humiliation! You won’t be able to hide your perversions for much longer and the first stranger who gets an eyeful of these panties will be in no doubt, will they? You’re a diaper wearing sissy baby girl and the entire town will know soon! It only takes 1 gossip, 1 big mouth and your disgusting secret is common knowledge, I’ll be laughing at every cringe and frown on your face as you display just what you’re really like! It makes me wet!”
Auntie Gemma had me step into her special panties, she pulled them up my legs and nestled them into place, making sure that my diaper was tucked away. Next was the garter belt which she deliberately had me wear over my panties, explaining that a lady wore them underneath her panties, so that she could pull them down to use the toilet, but as I was wearing my toilet there was no need and she would change me as needed. I sat on a small stool, as I gently rolled my silk stockings up my legs and attached the garter tabs. Auntie Gemma had me straighten the seams, looking over my shoulder, using the floor length mirror and asking me if I understood why my seams needed to be straight for her.
I told her that making myself pretty for her and wearing stockings, with seams was a way to demonstrate my desire to be totally feminised. If I was punished for having a wonky seam, I would be mortified, as I wanted to show the world my utter emasculation at the hands of her and could she please do me the honour of spanking the tops of my thighs, above the stocking tops, until I performed this task to her satisfaction. With a delighted laugh Auntie Gemma, spanked the tops of my legs, just as I was attempting to straighten my seams and she was revelling in my failure. Every time I got close, 1 of her slaps would jar my leg or knock my hand and I’d have to begin again. It took 5 minutes to do and by the end, my thighs were throbbing and glowed lobster red.
I sat down, put on my socks and Mary Jane’s before Auntie Gemma picked up my petticoat. There is no feeling, no item of clothing or humiliating task, that brings a sissy and her mistress closer together than when she petticoats him. I was red faced and looking at her with a pounding heart, as I stepped into that stiff lace concoction and It was soon tied around my waist, sticking out, horizontally. Auntie fluffed my petticoat and asked me if I’d prefer going out like this, no dress, just diapers, lingerie and my petticoat. I begged her not to shame me so and for once she relented, telling me that she was dying to see me in my dress. She picked it up, unbuttoned it and had me step inside.
“Wow, what a dress! It’s perfect for shopping for your wedding dress, Chrissy and I’m so happy you chose it! I think you should tell anyone who asks you, at the convention centre that you picked this dress for yourself and your pretty petticoat to! I’m sure everyone would be equally enthralled to hear about your choice of bonnet, but don’t forget to be on your best behaviour, so it’s Miss for all the young ladies and Ma’am, for all the mature women! Feed your arms through the sleeves, that’s it, they look so sexy, I love you in oodles of frills and this is beyond anything you’ve ever worn, isn’t it? Bet your having all sorts of little girl fantasies come true right now and I want you to know that, I’m right here, dressing you and letting you know that I understand! When I was a little girl, I loved my party dresses, petticoats and frilly knickers, my Mother would dress me like that for special occasions, but you’re lucky enough to dress like that all the time, aren’t you? Petticoat tickling, garters straining, diapers super soft and all your missing is your bonnet, isn’t it? Turn around and bow your head and we’ll complete your ensemble!”
The bonnet was positioned over my wig, my bunches hung from the bottom and I was turned around so that Auntie Gemma could tie a nice big bow at the back of my neck. Auntie Gemma primped and preened at my outfit, until she turned me around and displayed me in the mirror. I was simply distraught with the sight that greeted me in that mirror, it couldn’t be me, but when Auntie Gemma reached under my petticoat, inside my diapers, for a wee-wee check, I was bought back to reality with a bump. I looked like a sissy wet dream and I asked Auntie if she would please spank me, as I was feeling very spacy and needed to bought back to earth. With a laugh and a swift tug, I was over Auntie Gemma’s lap and under her hand.
Once again, she didn’t bother removing my diapers and plastic panties, choosing instead to concentrate on my upper thighs. I asked her why she always picked that spot and she told me that with my short dresses and petticoats, everyone could see that I’d been chastised. The thought that every eye on me would see that I was nothing more than her slave and that she disciplined me regularly, excited her. Sobbing and with my legs kicking a storm, I begged her not to stop and make sure that it was obvious that I’d been spanked by her. She told me that it would be her pleasure and she laid into me with a vengeance. I was a wreck when she pushed me off her lap and lifted her Nanny’s satin dress off to stand in front of me in just stockings and stiletto heels.
Auntie Gemma asked where my reins were, I pointed and soon found myself strapped in, being led to my former bedroom. I was asked if I preferred my old bedroom or my new nursery and with a little bit of trepidation, I replied that my new nursery suited me much more than this room ever did. Inside I was ordered to run her a bath and then return, so that I could choose her lingerie and clothing. I hurried and was soon deep inside Auntie Gemma’s pantie draw, my eyes as wide as saucers and licking my lips. I decided that panties weren’t needed, I mean the way her pussy dripped around me they’d be drenched in minutes. I picked a very stiff black satin and lace corset with 6 garters attached. Sheer black silk stockings, with a Cuban heel and pretty bows at the back of the ankle, were dangerously erotic in my eyes. I picked up numerous bras, but I couldn’t decide, so I opted for none.
The shoes were 6” stiletto heels, bright red and simply delicious. I wanted my Auntie to look sophisticated, so I laid out a sheer white silk blouse and red power suit with very short skirt and red leather elbow length gloves. I’d just finished, when Auntie Gemma returned, naked, but for the towel wrapped around her head, in a turban and covering her red hair. She inspected my selection, for a few moments and then asked me why no panties or bra. Looking down, I lisped that she didn’t need them and she’d be much more erotically charged going commando underneath such a short skirt. She giggled and said alright, but told me to kiss her lingerie now while she did her make up.
“I’ll feel like a right slut with no panties on, Chrissy, but if that’s how you want your soon to be married partner appearing in public, I won’t argue! Maybe I’ll meet a hunky bloke while were there and I can slip off to the toilet’s with him and have a nice anonymous fuck! Don’t cry, sissy, you won’t be alone, your Mommy and Jenny will be there and they’ll look after you, while I’m being filled with cock and you should feel free to wet your diaper! I’m going to fuck someone and I want you to know that you deserve to be virgin still! When were married, I can promise you, that you’ll die a virgin, as I won’t let that nasty bit of meat anywhere near a woman! The only fucking you’ll be doing is when I strap on a cock and force it in your bum! The look on your face, darling, its divine!”
I looked in her mirror and I was open mouthed at her latest assertion, Auntie Gemma was going to publically humiliate me, have me choose my own wedding dress and then she was going to pick some guy and fuck his brains out. I told her that it would be for the best, as I was sure that she needed a big cock after the morning she’d had and I pleaded for the right to ask her one night stand if he’d do me the favour of fucking my fiancé. She laughed out loud and promised me that I’d get the chance. I helped Auntie Gemma dress and when she was ready; I was astounded at her dangerous sexuality. She led me to my front door and opened the cloakroom next to it. Sitting there was an adult sized push chair. Made of aluminium tubing and with a pink Hello Kitty picture on it, I was strapped inside. Auntie Gemma picked up what was obviously my changing bag, filled to the brim and with “SISSY’S DIAPER BAG!” on the side.
Auntie Gemma asked whose car we should take and I told her that I’d thought of that. She picked up the keys I indicated and wheeled me around to the 6 doored garages at the side of the property. Sitting there was a very special van, like a Pope mobile the rear was made of open glass, with nowhere to hide and the front compartment had tinted windows. It was a vehicle with 1 function and 1 purpose, to expose the rear passenger to everyone. Auntie Gemma laughed and told me that I was in for a real treat, as she lowered a rear ramp, wheeled me inside and strapped my push chair in to special fittings. She retreated and locked up the door, I was alone for the first time in hours. Auntie Gemma got in and started the engine, a small screen coming to life at my feet and showing hardcore sissy porn. The intercom crackled to life and I was asked if I was ready. I was shivering in fear and begged her not to publically humiliate me, but she laughed at my crude attempt.
“It’s all a little late for begging, Chrissy! You should have thought through just what public humiliation entails before you bought such a marvellous van, for us to us and enjoy together! Now the convention centre is pretty close and we’ll be there soon, so don’t worry if you panic and do wee-wee! Even in this van, you and I will be the only ones to know, well at least until we arrive and I show Mommy and Jenny your disgraceful wet diaper! We’ll soon have changed and in to the exhibition though, so everyone can see! Chin up, darling!”
We set off and was in a total panic, I was about to be outed publically, but not as something as so societally acceptable as a homosexual and I was horrified. I was to be shown as that strange creature, the sissy and not just a lingerie wearing butch guy, who was just playing, but an utterly vile sissy baby girl. As we left my long drive way and entered traffic on the main road, I was turned into an object of ridicule for total strangers. A coach full of lads pulled a long side of us and I was turned into a sideshow for their entertainment, when Auntie Gemma’s voice told me to lift up my petticoat and show the nice boys my panties. I was horrified, when she ordered me to look each them in the eyes and either wink, blow them a kiss or lick my shiny lips. I felt an inch tall, as these lads were given a show.
They pulled off soon after, but we were quickly entering town and heavy afternoon traffic. I was surrounded by buses, vans and cars, all of the passengers having a long look at me. Most seemed disgusted, a few curious and a couple outright lecherous. 1 enterprising van driver held up a sign asking if I needed a diaper change. I screamed as Auntie Gemma laughed, she’d lied and my diapers were on view to all. I lost control and in a moment of utter humiliation, I wet my diapers like a little girl and started to cry. My Auntie must have smelled blood because she was asking me why I was crying and when I stayed silent she accused me of wetting my diapers. I tried to stay silent, but she told me that as a punishment, for not lasting until our destination, she would take the ring road. Twice as long and lots of traffic lights, pedestrian crossings, I would have hundreds of eyes looking at me and some of them would be able to see the wet patch through my sheer rhumba panties.
“Has my darling fiancé had a nasty accident in his diapers? Not talking are you, well I can tell, you’ve gone wee-wee in your own wearable toilet and do you understand why we decided to put you in diapers? Nasty sissy’s like you can’t be trusted that their toilet training will survive such intense humiliation and we were correct, weren’t we Chrissy? 1 little drive through town and your unable to control you most basic bodily functions, are you? Well the first thing to do when we arrive is find your Mommy and Jenny, tell them about our wedding plans and then get you changed into some clean, dry diapers and show you off!”
The next 15 minutes were a blur, but I was at least able to stop myself from humiliating myself further and when we pulled onto the convention centre car park, driving around the back, I thought I was being spared a grand entrance, but the wedding designers were using the smaller rear hall. I waited a few minutes, but Auntie Gemma was in no rush to get me off of display and inside. The reason became obvious shortly, when my Mommy arrived being driven by my step-sister Jenny. They pulled right next to us and they all got out, hugging and greeting each other. I was noticed by Jenny first and it was she who opened the rear door and entered. She stood beside me, crouched down and lifted my petticoats, taking in my lingerie, the message on my rhumba panties and the wet patch inside my diapers.
“Well you’ve been busy, haven’t you? Filling your diapers with a nasty enema, this morning and when you’re Auntie takes you on an outing you lose control and wet yourself! My own step-brother, nothing more than a diaper wetting sissy and if your Mother could see you now, do you know what she’d say, Chrissy? She’d tell you that you deserve everything that’s been done to you and everything that will be done! You look beyond what any woman ever think of dressing like and wait until everyone inside gets an eyeful! You’ll be the talk of the town and I’ll make sure that all the stories Gemma has been telling me get out, you know the really depraved creepy stuff, so that you’ll be a laughing stock!”
I was sobbing, as Jenny unbuckled me, wheeled me down the ramp and onto the car park. Auntie Gemma locked up, my diaper bag over her shoulder and a spring in her step. We entered a foyer and crossed to an information desk. A young girl, perhaps 20, blonde and cute looked up, doing a double take. She tittered, as Auntie Gemma asked her where the baby changing room was, as she needed to change her baby’s wet bottom. I cringed, but the looks on the ladies faces were angelic, as I was subtly humiliated in front of this stranger. She introduced herself as Louise and asked if I’d really wet my diapers. Mommy explained that I’d lost control and messed myself on the way over. She grinned and leant in, whispering into Louise’s ear. She stared at me even harder and commented that you’d never know what was lurking inside my diapers without an explanation. She pointed across the foyer and we headed over.
Inside the room it was reasonably spacious, with a sink and a large metal changing table, at waist height. Auntie Gemma unstrapped me from my push chair, while Jenny sorted out fresh diapers, baby oil, powder and dry plastic panties. Very similar to what I was wearing under my rhumba panties. Mommy pulled my petticoat up and Jenny lifted my legs to access my bottom. She was swift and in seconds my damp derriere was being inspected. As Jenny cleaned my bum with baby wipes, Mommy was asking about my lobster coloured thighs. I was asked why my Auntie had punished me and whimpered that I was a naughty sissy. Jenny had oiled her hands, using the left to coat my balls and the right to lubricate my bum. Auntie Gemma grabbed my ankles and lifted them around my ears, giving Jenny complete access to my hole. She teased me and asked me for the truth. Was I going to marry my Mommy or my Auntie? Red faced I said Auntie.
“Congratulations, Gemma, half of my step-brothers money is yours for the taking, but you’ll be continuing his babifacation I hope? That’s excellent news, as I love to see Chrissy dressed like a girly and humiliated for our pleasure! When you called earlier, I had to sign off to masturbate, I do hope you understand, but when you explained that he’d p*o-p*o’ed in his diaper, I needed to wank and I came 3 times! I’ve never been so sexually charged and by spending time with my step-brother, wearing a little girls dress and changing his wet diaper! Gemma would you take over for me, I’ll just nip next door and have a quick rub! What! Do it her, with Chrissy watching, isn’t that close to i****t? Well I suppose as were not blood related and you’re sure he’ll be embarrassed that I’m wanking over him! Ok then, here goes!”
Jenny lifted her skirt, pulled her red silk panties out of the way and began a hard, fast wank, right there my bum being powdered and pinned inside my fresh diapers. As I had my fresh plastic panties pulled up my legs and positioned to prevent any leaks, Jenny orgasmed and I looked at her in shock. My prim and proper step-sister was clearly a slut in training, so when Mommy approached her, drew her into an embrace before kissing her deeply, their tongues en-twining and losing themselves. I was stood up and helped into my rhumba panties, had my garter tabs attached and helped to straighten my crooked seams. By the time we left the changing room, my 3 dominants were once again the vision of female beauty, while I was a joke. At the reception Louise had been joined by 2 more young ladies and they were giggling, as my situation was revealed.
Auntie Gemma thanked the receptionist for her help and told her that my wet diaper was gone, replaced by a clean dry one. She asked Auntie Gemma why I was dressed this way, was I being punished and using a diaper like a little girl. She laughed and explained that I had asked to be treated this way; in fact they were here to find me a wedding dress for my forthcoming nuptials. They couldn’t believe anyone would marry a loser like me, so when a real beauty like Auntie Gemma explained that she was marrying me, they were flabbergasted. I was made to listen, as Mommy explained that it was purely a matter of getting my money and there would be no intercourse to consummate the marriage, as I was locked away in chastity, for my own good and that Auntie Gemma would continue to sleep with as many guys as she wanted. Louise laughed, calling me a sissy cuckold and a diaper wetter.
“He’s exactly that, you know a sissy cuckold and a diaper wetter, but there’s more isn’t there, Chrissy? Tell the young ladies about your sex life before we locked you in chastity! It’s true, our sissy’s never had fucked a woman and he never will now! So the easiest way for your fiancé to get satisfaction is in another’s bed, isn’t it? Her in sexy lingerie, taking cock in every hole, a complete slut, while you’re at home filling your diaper and imaging her being pleasured over and over again! Don’t cry, after all you’ve always wanted this haven’t you? Wanted to be humiliated by strong, dominant women and turned into a whimpering sissy, for their satisfaction! Now let’s head inside and find you a dress!”
Leaving a stunned silence behind us, Jenny pushed me through some large doors and into a well lit room. It was very large and was half filled with stalls and masses of women. Looking carefully, I only spotted about 8 or 9 men, out of the 100 or so occupants. The first few minutes passed without incident, but when we approached the first stall, we were spotted by an older lady, who elbowed a much younger lady in the arm and pointed at me. We arrived with both ladies smiling like sharks. Mommy asked if they could make made to measure designs and patterns, as we needed a very special dress for a very special wedding. Asking who the dress was for, Auntie, Mommy and Jenny turned to me and the2 ladies burst into laughter.
They asked if I was a man inside my very pretty dress and Mommy told them I had never been a man, not really, but there was a cock locked away in chastity, deep inside my diapers and was not needed. I was so ashamed, as Auntie Gemma explained that I was filthy rich and she was marrying me for my money. The older lady remarked that was a very sensible idea and more women should follow her lead. She asked me directly, if I liked my pretty dress and I lisped that it made me feel like a real girl. When people laugh, it’s usually a communal jovial experience, but I was the butt of this joke and was teary-eyed, at the on-going humiliation. The older lady introduced herself as Marie and the younger woman as Becky. She asked if we’d like to step inside and view some of the options available.
The curtained off space was packed with racks of wedding dresses and boxes of the most delicate, sensual lingerie meant for the wedding night boudoir. My dominant ladies sat down with Marie and launched into a deep conversation about what they wanted my dress to look like. Becky approached me and looked me up and down. Mommy turned and told to feel free to get hands on, as I was under their control and wouldn’t resist any woman’s touch. Becky reached under my petticoat and lifted it out of the way, exposing my diapers and chuckling softly. She asked me if I was in need of anything and I whispered that I was thirsty. She asked Auntie Gemma, if she could get me a drink, but she reached into my changing bag and handed her a full bottle of formula. With a smile, Becky asked me to open wide and drink all of my formula like a good girl.
“That’s such a lovely dress, Chrissy; did you pick it out, yourself? You did, well you’ve got exquisite taste and your bonnet is simply gorgeous! If I ever have a little girl, I’d dress her ultra-feminine, just like this and she’d love it, well till she reached 3 years old and outgrew it! You clearly haven’t grown up, to dress like this and still be in diapers, but I wonder, you don’t still use them do you? You do, well I have to tell you that’s alright, sometimes accidents happen, don’t they and you’ll be very safe inside such big diapers, won’t you? I wonder if my boyfriend isn’t right for diapers, you see he loves it when I bring home samples of lingerie, from the shop and dress him in them! He gets a very big stiffy in frilly knickers and he fucks me, but spurts in seconds! Maybe he’ll last longer if I dress him as a little girl, in diapers and petticoats!”
She was very earnest and Auntie Gemma over heard, she told the young girl to check my diapers and I begged not to be shamed. Auntie Gemma just laughed and told me to beg Becky to give me a diaper check. In my lisping voice, everyone listening intently, I begged Becky to give me a diaper check and she smiled. Lifting my dress and petticoat out of the way, she reached down the front of my rhumba’s, into my plastic panties and entered my diapers. She was grinning at my discomfit, but when she found my chastity covered cock, she seemed bewildered and I told her that Mommy had locked my cock away. She recovered quickly, asking me how often I was released and told her never. Her eyes twinkling, I was asked if that wasn’t incredibly frustrating and I nodded. She tickled my balls and asked why they seemed so small.
I told her in a hollow voice that Auntie Gemma had milked me this morning, while giving me an enema and I’d shamefully leaked all over my enema table. This made an impression and I felt her reach deeper into my diaper, to explore my bum. So far we’d been whispering to each other, the others conversation loud enough to disguise most of our discussion, but in a loud clear voice, Becky asked me if I liked it up my bum. The room hushed and all eyes focused on me. I remembered Auntie’s warnings to obey any lady we met and I obeyed her command. I lisped that I loved it up my bum, that I loved be fingered by Auntie Gemma and had been fucked with a big dildo, as well under her authority. Becky laughed and told me that she didn’t believe for a second that I was telling the truth and demanded proof. Mommy told me that I should defend the honour of my mistresses and I should prepare for examination.
Jenny prepared me, removing my diapers, plastic panties and rhumba panties, till I stood in a small room with 5 fully clothed women and I was bare ass naked. I was on the floor, lying on my back, on my changing mat, my feet in the air and a bottle of baby oil beside me. Mommy passed Becky some latex gloves and she pulled them on, tightly and knelt down next to me. She was wearing a light summer dress, short, with a yellow flowery print, sheer white tights and beige 6” stiletto heels. She was very much the girl next door and I responded to her very submissively. She took hold of my ankles and inspected my chastity covered cock and my bottom. She asked me if I’d ever gotten hard in my chastity and I explained that I couldn’t, that even a slight engorgement was painful. She asked Mommy where she’d gotten my chastity, telling her that her boyfriend needed 1 urgently. Mommy told her, as Becky poured oil all over my bum and coated her right hand. I was open, but Becky asked Jenny and Auntie Gemma to hold my legs wide so that she could get total access. I was spread for a fingering. A fingering from a woman that I’d met just 15 minutes ago.
“Now then Chrissy, let’s see if you really are an anal slut or if you’re a big fibber! Now I’ll start with my index finger and see if it fits! Wow, your bum is so soft and welcoming, but maybe it’ll be scared by a second finger, hmm? That’s it Chrissy take 2 fingers like a good little sissy and we’ll all be so impressed, won’t we ladies? This naughty sissy baby has 2 of my fingers up her bum and she’s squirming like a horny slut, all frilly and lacy, but we know that he needs to wear diapers, just like a real little girl! You mess your diaper’s, don’t you sissy? Fill them with wee and p*o, like a dirty girl and your friends clean and change your bottom, putting you into fresh diapers! I’d love to change your wet diaper, sissy, I’d clean your bottom, oil you up and finger you till you begged for something bigger, but I’ll just show everyone, here comes finger 3, that’s a good girl! Look Chrissy’s taking 3 fingers up her bum and I’m sure we’d all like to give her a big round of applause!”
I was given a slow humiliating round of applause, as I was bought over and over again, to the edge of spurting, her fingers massaging my prostate. She asked me if I was ready to spurt and excitedly nodded. She looked deeply into my eyes and said very good. With no regard to my dignity or my impending orgasm, Becky deliberately re-diapered me and pulled up my plastic panties, then my rhumba panties before strapping me into my push chair. Crouching in front of me, her hand resting at the top of my thigh, caressing my stocking tops, she asked if I was feeling better. I shuddered and told her that I was so close, begged her to finish me off and make me spurt for her. She laughed and said that this was much better, I was wound like a spring and any little humiliation or chastisement would fell so much more intense. She told Auntie Gemma that I was hot to trot and would be very submissive for a while.
Auntie Gemma laughed and tested the assertion. She asked me to tell everyone, what I’d begged her to do with my potty and then carried out in front of her. She’d promised not shame me with this story, but she was grinning evilly, as I begged her not make me. Jenny told me that I’d better confess my dirty little secret or she’d take me out to reception and pull down my diapers, drag me over her lap and spank me right there. A bare-bottomed spanking, in reception, with the 3 young receptionists’ watching as well as whoever else is around or 1 little story for 4 eager ladies to enjoy. Teary eyed, I explained that I’d begged Auntie Gemma to lick my potty clean, after she’d washed it, in front of her and I did. I was so ashamed and begged to be punished for such a dirty act. Becky took my hand and in a calm soothing voice told me that I was very brave to admit to such a naughty, disgusting act, but I needed to be punished immediately. I nodded at her and she smiled.
She unstrapped me once again, stood me up and bent me over at the waist. She lifted my dress and petticoat up, displaying my scarlet thighs; she was gently rubbing my punished flesh and telling me that she was going to add to my lovely glow. She asked Auntie Gemma if she could punish me for being a nasty perverted potty licker and she was adamant that I needed sterner correction than a spanking. Marie asked if a wooden paddle would be suitable. She dug inside a pile of lingerie and pulled out a 3’ long, 8” wide and 1” thick paddle with half a dozen air holes in the head to allow greater velocity. Mommy clapped her hands and asked Becky to paddle my bottom, for being a dirty potty licker. As Jenny once again removed my diapers and bought my bottom on display, Becky had me kiss the paddle.
“Now then Chrissy, I’m going to enjoy this very much and I’m sure everyone her is in agreement with this discipline! Begging your Auntie to lick your potty clean and then doing it right in front of her! Absolutely disgraceful, but we’ll give you the chance to redeem yourself, instantly, but I should tell you that this will hurt you dreadfully and I’m sure you’ll cry out in pain so I’m going to gag you! No need to disturb all the ladies looking at wedding dresses, by listening to you screams of agony, so open wide and chew on these! Marie’s delicate French knickers, a perfect gag for your discipline and perhaps a little restraint as well! Jenny and Marie, would you each take 1 of Chrissy’s arms, pull him tightly across the desk and make sure he takes every stroke! There’s 5 ladies present, 5 ladies you’ve offended, so how about 50 strokes with the paddle? I could always give you 60 if you prefer? No, well 50 it is, ready?”
I was struck, very hard across my bottom, my eyes bulged open and I shuddered. I was in for a real beating and I couldn’t stop it. Becky was without pity, striking me over and over again, without rhythm or warning. I was screaming into my gag before I’d even realised that she’d gone again. She was very strong and I was delirious from the pain, but I spotted Jenny’s fingers under her dress and inside her panties as I was beaten. She was masturbating to my pain and she wasn’t the only 1. Both Auntie Gemma and Mommy were wanking, their legs spread and dresses up. I was close to fainting when she reached her 50, but I wasn’t allowed relief, instead Becky told me that I would take 20 more for being such a naughty tease. I tried to speak and Jenny removed my gag. I told her that I’d gladly take 30 more, but could I please have another pair of dirty knickers to suck as these were clean. Mommy laughed, pulled her knickers from around her ankles and passed them over.
I was beyond pain as I took those additional 30, for my ladies and for my disgraceful behaviour today. At the end, Becky had me kiss the paddle before she re-diapered me yet again and led me around to each lady, to suck on her stiletto’s and promise to be a good girl. We left that stall 10 minutes later, looking much like we did on arrival, but for my sore bottom and some well satisfied ladies. We headed deeper into the room and Jenny spotted a lingerie stall. Every piece was vintage 1950’s Betty Page style, all panty girdles, corsets, silk knickers, silk stockings and massive stiletto heels. Jenny was smitten by the display and we entered the booth. A stern woman and a young black man were selling the vintage lingerie; she introduced herself as Miss Leanne and her friend as Errol. She seemed un surprised at my appearance.
She asked Jenny if she liked her designs and she said very much. She asked what they were looking for today and Auntie explained that I needed a wedding dress for our special day, but that maybe the Maid of Honour, pointing at Jenny and the Best man, pointing at Mommy, would like some very fancy lingerie for under their clothes. Auntie seemed very flirty and wanton, it dawned on me that she was attracted to this young black man, but he was open mouthed at her agreeing to marry someone like me. She laughed and explained that it was a marriage in name only, so she could access half my money, but she would continue acting like a single woman. She winked at me and I took it as a cue to fulfil my promise from earlier. In a quiet voice, I asked Errol if he’d like to fuck my fiancé, as was a diaper wearing sissy baby and I’d had my cock locked up in chastity.
Miss Leanne snorted at my plea and told me that I was obviously sincere in my request, but Errol shouldn’t be rash. Maybe he’d be willing to fuck Auntie Gemma, if I bought Jenny and Mommy some of her vintage lingerie and promised to ask her permission for being so disgusting in her presence. I opened the little purse Auntie Gemma had given me, pulled out my platinum American Express and asked her to ready every item in Jenny’s and Mommy’s sizes and I’d buy them all. Errol looked at me with utter contempt, told me that he thought my fiancé was not all that, but maybe he’d agree if I told him about how good she was in the sack. My face fell and Mommy explained that I was still a virgin and would never be allowed to enter a woman, sexually. Miss Leanne stared at me with hooded eyes.
“I love virgin sissy girls, all pent up and locked away for their disgraceful urges, but they’re usually much younger! How old is this 1? 40 well, you’ve fallen on your feet haven’t you? No chance of spurting, but wearing sissy dresses is much better, isn’t it? Don’t worry, Errol’s more than enough of a man for your Auntie, but are you enough of a sissy for me, as he won’t go near her pussy without my say so! If you tell you’re Auntie that Errol is a real man and makes you feel inferior to him, before begging her to please fuck his big black cock! After that, would you please beg, Errol to take pity on your horny fiancé and please cuckold you, I’ll be some way towards granting your wish! It’s so refreshing to hear a sissy trying to seduce a real man for his mistress, but maybe if you offer to help them fuck each other, as a, well as a fluffer! You could strip Errol naked, get on your hands and knees before using your mouth to get him rock hard! You do want her to have a very big hard cock don’t you? Well this is the best way and I’m sure she’d appreciate you guiding his cock into her pussy before you leave! Once it’s buried deep in her your useless and should come and tell me all about it! Go ahead, sissy!”
In a tiny voice, I obeyed Miss Leanne and shamefully repeated her words, 5 people hanging on every word. When I finished, Errol laughed and told me sure, he took Auntie Gemma’s hand, pulled her into an embrace and kissed her, passionately. His hands cupped her bare bottom, through her dress and remembered that I’d insisted that she be pantie less. Auntie beckoned me over, took my hand and we headed behind the curtains, to a small open space, being used as a stock room. Errol continued his rough treatment of Auntie Gemma, but she seemed to love it. The fondled and kissed for a while before Errol turned to me and said it was time. I removed his shirt, shoes, trousers and finally his briefs before sighting his cock. It was huge and I gasped, Auntie Gemma was surprised as well and wondered if it would fit her pussy. Errol laughed at her and told to shut her slutty mouth, he was in charge and she shouldn’t forget it.
Auntie Gemma was clearly enjoying obeying this alpha male and when he told her to remove her suit and blouse before masturbating for him she was quick to do as he commanded. Errol pointed to the floor in front of him and smiled, his cock twitching. I’d never found any man sexually attractive and Errol was no different, but I’d promised to get Auntie Gemma laid and she expected me to do anything required of me to make it happen. I bought my mouth up to his cock; he grabbed the back of my silk bonnet covered head and forced himself down my throat. Auntie Gemma told me that I’d never looked quite so sexy and I should hurry up, she needed a hard fucking. Errol was fucking my face, forcing his cock deeper and deeper; all the while I gagged and choked.
Errol pushed me away and I looked at his monster, my saliva coating it and shivered at the thought of it entering Auntie Gemma. Errol told me to stand with my legs either side of her head, holding each ankle and spreading her open. Errol sank to his knees, placed his cock at her entrance and told me to put it in her for him. She begged for more lubrication and he had me spit on her pussy. She was scared, I could tell and when she asked about birth control he just laughed, telling her that he on rode bareback and she should be hoping that his spunk knocked her up. He asked me if I’d raise his black bastard for her and do so like a good sissy. Sobbing, I told Auntie Gemma that I’d be so proud for her to get pregnant by another man and I’d be so grateful to able to raise the c***d. She told me that was very good, but it was time. I slowly guided Errol’s cock into my fiancé pussy. Her face showing pain and I begged to be allowed to stay and watch. Errol told me to fuck off and come back when he was finished. I left the room to the sounds of flesh slapping flesh and deep moaning. I stood behind Miss Leanne and waited for her to notice me. She turned.
“Here you are and what a good job you’ve done sissy, I don’t know many sissy’s who’d become a fluffer for his fiancé, but you’re special, aren’t you? Did Errol treat you like a whore and fuck your face? He did, well maybe your Auntie didn’t see? She did, well that’s unlucky, and so she knows that you’re a cocksucker, but she wouldn’t use that against you, would she? Maybe she’ll invite some of her boyfriends around and have you entertain them before they go on a date! You on your hands and knees, cock in mouth as they chat about their plans and ignore you completely! She wouldn’t be that cruel, sissy? She would, well I’m very sorry that I had you suck Errol’s cock then, I’ve obviously opened a door that should have stayed closed, but I’m sure you’ll learn to love sucking cock and if you don’t, well who cares, you’re a sissy and nobody will bat an eyelid!”
I stood there, humiliated beyond believe, as I listened to the savage fucking happening 10’ away and I begged Miss Leanne to let me by, but she shushed me and had me listen harder. They were getting louder, as Auntie Gemma was crying in ecstasy and I longed to be able to do that for her, but I was unable, so I just listened. For 15 minutes, that savage fucking entered my mind and chilled me to the bone. When it final ceased, Miss Leanne told me to go on in and help Auntie Gemma. Errol was dressing and paid neither of us any mind, I knelt by my sweaty mistress, her hair dishevelled and her make up running and very quietly told her she looked very beautiful to me right now. She smiled and asked me if I was feeling alright and I tried to explain, just how much the sound of her fucking another man had affected me, but she smiled and told me to help her stand.
Her corset needed tightening and her stockings were ruined. She told me to ask Miss Leanne for a pair of fresh stockings and a mirror for her to fix herself. I obeyed and returned quickly, a packet of barely there, seamed, Cuban heeled silk stockings and a mirror. Auntie Gemma fixed her makeup, as I removed her laddered and torn stockings before replacing them with new 1’s. I was behind my Auntie, straightening the seams, when Miss Leanne entered and joined my Auntie, ignoring me, as I fiddled with the silk. Miss Leanne asked Auntie Gemma if she’d enjoyed her fucking and she very crudely explained that Errol’s cock had filled her to the brim and she needed to have it again. Miss Leanne explained that she owned Errol’s cock, after he wagered his manhood would bring her off and he’d failed miserably. She seemed to want something from Auntie, but she was very reluctant to say so in my little girl’s voice I asked Miss Leanne if I could do anything to secure the services of Errol’s cock for my Auntie.
“There’s an idea that I’ve had for some time and Chrissy here could be perfect for it, in fact he’d be a real star, but it would mean complete and total exposure of his sissy life! No going back after this, just spending everyday as the slave of capricious and demanding women, but you need to agree right here and now, no backing out and no escape! Gemma I’m going to expose, Chrissy’s life on the internet, chronicling his trials and humiliations as movies and pictures! I’ll charge perverts to get off on her servitude, keeping all the profits and in exchange Errol will fuck you once a month! 1 night, all night and he’ll even do you in the bum as well! I’m sure a slut like you would enjoy being buggered, as you’re bent over your sissy’s cot, moaning as your filled to the brim and he’s left to watch, your slave and my money maker! I’ll have a contract drawn up and he can sign it at your wedding reception, Errol’s first night could your wedding night and I’ll babysit, Chrissy, live on pay per view!”
I promised and we left that back room with a sense of accomplishment, I’d managed to get her a massive cock once a month and she’d found another way to have me humiliate myself. We re-joined Mommy and Jenny, they were surrounded by bags and they promised to show us all there purchase’s later. Mommy strapped me in my push chair, while Jenny gave me a big hug and told me that she was very proud of her sissy step-brother. Becoming a cocksucker, showed her that she really did need to be in my life once again, to enjoy my degradation and even add to it. She promised that she had a surprise for me and did I want to know just who would be joining us shortly, while I’d been assisting out back, she’d called her daughter and invited her to join us. Jade was 19 and studying psychology at university. Apparently I was a fascinating case study in submissive deviant behaviour and she’d begged her Mother to let her meet me and this was the perfect moment.
Jenny whispered in my ear that I should tell Jade all about my recent cocksucking adventure, making sure to explain that I wasn’t gay, but nothing was taboo if my Auntie Gemma ordered me. Jenny reached inside my diaper and gently massaged my bladder, making need to pee. She looked at me and asked if I’d like Jade to change my wet diaper, I nodded and she told me to tinkle or she’d have nothing to change when she got here. I tried, but failed miserably, begging Jenny not be mad and that I’d wet my diaper very soon. She grumbled stood up and picked up her lingerie filled bags, just like Mommy and Auntie Gemma took my hold of my push chair. We left Miss Leanne’s stall and headed to the far end of the room, with every eye on me and laughter echoing in my ears. We found 1 stall all on its own and called for help. A very petite Asian woman, dressed in a form fitting blue silk dress and 5’ black stiletto high heels welcomed us and asked how she could be of service. Mommy explained that I needed a custom wedding dress as soon as possible and could she help us.
She looked me up and down, taking in my attire, especially my diaper and asked if the sissy baby wanted a really humiliating dress. She looked at me coldly and told me that I’d be so worried about wearing the dress she had in mind that I’d wet myself. She reached down and patted my diapers, telling me that she’d make sure that I’d need a much bigger diaper under her dress. It would be every sissy’s dream of a wedding gown, but I’d need a real willingness to listen and obey my intended as she would be the only 1 with the key to unlock my dress. Auntie Gemma told her that she would be marrying me and she wanted to see me all in white, for my wedding day, as I was still a virgin bride after all. The Asian wedding dress designer sniggered and asked me if I was still a virgin, I nodded yes and she smiled at me with contempt at my predicament. Jenny explained that she wanted a long sheer veil included floor length and decorated with crystals. Mommy looked at me and smiled before telling the woman that I should have a very frilly set of petticoats, perhaps more than 1 and they should be very stiff and drip with lace. The Asian lady giggled and asked me if I’d like 4 huge petticoats, under my dress. I nodded, just as our newest guest arrived. Jade, Jenny’s blonde daughter waved at her Mother and joined us.
She was very pretty, quite tall and softly spoken, dressed in designer jeans, stiletto heels and a white off the shoulder loose knit jumper. It was so loose knit I could see her bra through it and she was clearly trying to make an impression on me. She ignored me till last, Jenny introducing Mommy and Auntie first and even telling her that we’d found someone to make my wedding gown. Jade squatted beside me and asked me if I knew who she was. I told her that she was my step-sister’s daughter, Jade and that she’d asked her Mother to introduce us. She giggled and told me that I’d missed the point, that she was something much more important and she was looking forward to spending time being the niece of a sissy baby girl. She whispered in my ear that I’d better have a wet diaper because she was really looking forward to changing me. She unstrapped me, stood me up and gave a very big hug, her breasts rubbing mine, her perfume filling my nose and her hands crinkling my diaper covered bottom. I was unable to stop myself and I wet my diapers. Jade felt me slump slightly and my diapered bottom warm. She looked me square in the eye and asked me if I’d wet myself. I sobbed yes and begged her not to shame me. She giggled and told me that she’d want to do something like this for a while.
“Excuse me everyone, but I thought you should know that Chrissy has wet her diapers! Fancy losing control, like that, when she’s getting a nice friendly hug from her niece! Do you think we should all check out her messy diaper, ladies? Yes, well if we could just ask this lovely lady if we could use her backroom as a make shift changing station, we’d all be all be very grateful, wouldn’t we? Lead on then and let’s see just what’s happening inside these very full diapers!”
The Asian dress designer introduced herself as Miss Wei and beckoned us, all; inside her feminine filled space and pointed to a small platform in the centre of the room. She told my niece, Jade, to use it as a changing table and asked the others to sit in the seats surrounding the dais. I would be on display for this latest public diaper change and I revelled in the shame of it all. Jade took my diaper bag from my Auntie Gemma, removed my changing mat and laid it on the platform. She patted the plastic mat and asked me very seriously to lift my dress and petticoats out of the way, so that she could inspect my diapers. She bent down and sniffed my behind. I cringed as she announced that I hadn’t done a p*o-p*o, but that I was very wet. She smiled and asked me if I was a regular diaper wetter. I nodded, utterly humiliated by her seeming tender nature and flummoxed by her caressing my arm.
With a delightful touch, Jade, checked every item of my clothing, asking her Mother if I was dressed like this all the time and receiving an affirmative, she whispered in my ear that I was a very lucky sissy. She gently positioned me on my back, my legs in the air and my diapers on show. She never stopped caressing my upper thighs, still red from my punishment and asked if I’d been a naughty sissy baby. I lisped that I had been taught that I needed regular chastisement, for being so perverted and I was appreciative of such deserving lessons. Jade reached inside my diaper bag and removed all the items she would need to change my dirty diaper, showing me a pair of divine prissy baby blue silk and lace rhumba panties. She passed them to Miss Wei and asked her if she thought I would look good wearing them, she smiled and told Jade that she was sure that I’d be the frilliest little sissy baby at the show today.
Jade lift my legs, holding them up by my silk covered ankles and proceeded to strip my panties, dirty diapers and exposing my bottom to all the ladies. Auntie Gemma pointed to my chastity covered cock and told Miss Wei that I’d been locked away for my own good. Jade seemed pleased at the sight of my cock under control and asked me if I was very frustrated at my confinement. Humiliated and fawning at her direct question, I told her that I was better off locked away and begged her to not be so shaming. She laughed and told me that I loved it and asked me not be ashamed at her questions. She pulled out some wipes and began to clean my dirty bottom.
“Chrissy, you don’t think we understand that wearing sissy baby clothes, naughty lingerie and big soft diapers, is better for you than making spurties, like a big boy! It’s all you desire, isn’t it, to be humiliated and degraded by strong dominant ladies, while wearing silk and lace? I think you should tell us that you want to be locked up forever, with no hope of release and teased relentlessly! Go on, tell us and I’ll tickle your throbbing balls! Maybe I’ll even push a finger in your bum, like a pretend cock and finger your nasty hole, while everyone watches and laughs!”
In a lisping voice, I obeyed my young niece and gave away my dignity, once again. I was the object of mirth for those 5 ladies and I didn’t care a whit, because my niece had fulfilled her promise and was gently frigging my bum. She poured baby oil onto her hand, eased her middle finger into my hole and in front of my audience, pushed it inside me. I sighed at her intrusion and whimpered when she added a second finger, slowly thrusting in and out. Jenny sat on the platform, next to my head and asked me if I liked her daughter. I gasped and told her that Jade was very lovely. She smiled, lifted my face up and kissed me on the forehead before telling me that I was correct. Jenny asked me if I’d like Jade to be my bridesmaid at my wedding, but I should know that she’d want to bring a few of her friends from university and they’d have to see me dressed like a total sissy.
Right at that moment, Jade, added a third finger and I was her’s. In a panting voice I begged Jade to be my bridesmaid and asked her to invite whoever she wanted to my wedding, as long as it was alright with Auntie Gemma. Jade looked over to Auntie Gemma and she just said to feel free to invite anyone she wanted to. Jenny laughed and told me that I’d love all her daughter’s friends, especially the twins. I looked at her and she winked, telling me that it would be a surprise on the day. Jade frigged my bottom with gusto, her mother looking on and I begged for a milking. She pulled her fingers out quickly and I gasped from the speed of it.
“I don’t think you need a milking right now, Chrissy! In fact, I think you’d be much better behaved if you were feeling particularly impassioned right now! I’ll just powder your bottom and get you inside these lovely soft diapers! Don’t cry, silly, you do want me to diaper you, don’t you? Well then, let’s have no more silliness and maybe I’ll spank you later, instead! That would be much sexier, for me, than watching you milk and you do want to please me, don’t you? That’s settled then, bum up and I’ll diaper your bottom, then!”
My niece pinned me inside 3 pairs of massive pink cloth diapers, covering my powdered bottom before lowering my stocking covered legs and asking her mother if I needed any plastic panties to prevent leaks. Jenny giggled and explained that I was a very heavy wetter, so she should definatly have me in some plastic panties. Auntie Gemma suggested a pair of opaque baby blue plastic panties with a ducky on the front and told her where to find them. I was once again on display, as Jade lifted my legs and pulled on those very c***dish plastic panties. They were very crinkly and made a great deal of noise, as I was stood up and told to show everyone my panties and I obeyed. I was mortified, as all the ladies crowded around, felt up my bottom and commented on the fact that I should thank my niece for diapering me so nicely.
Timidly, I followed my order and Jade smiled at my delivery. She asked me if I’d like her to put my frilly rhumba panties on and when I nodded; she picked them up, opened them wide and told me to step into them. She pulled them, slowly, up my legs and settled them over my massively diapered bottom, making sure to tuck everything underneath them and I sobbed at the shame of it all. She asked her mother for a pacifier, as I was such a cry baby and she was fed up of hearing my whining. In moments I was sucking away, standing next to my niece, her hand in mine and her perfume in my nostril’s. She told me that I was a very dirty little girl and I should have my bottom spanked for making such a disgusting noise. I was unable to control my emotions, as I’d been teased and humiliated so expertly, but my degradation wasn’t over.
Auntie Gemma asked Miss Wei if she’d measure me for my wedding dress now and I was once again helped up onto that platform. I was intimately gauged for my ultimate feminisation and I was made to feel like a complete sissy by that intimidating Asian woman. Not an inch of me was unchecked, as she touched me up like a cheap whore and I took it. She noted my measurements on a small notepad, with a pencil and tutted all the time. When she reached inside my diapers and fondled my chastity covered cock, I shuddered but Mommy just told me not to be such a wuss. When it was finally over, I was strapped back in my push chair and made to watch as Mommy, Auntie Gemma, Jenny and Jade went through a much more normal measuring session. Jenny and Jade sat beside me took my hands in theirs and whispered in my ears, as Mommy and Auntie Gemma gave Miss Wei a detailed description of my dress. I wasn’t allowed to hear.
“It’ll be such a surprise on your big day, won’t it? We’ll be able to see just how much of a sissy baby bride you’ll be and I bet you’ll love it! You’ll be so girly and prissy, but that’s what you need us to witness, isn’t it, Chrissy? I can’t believe just what a sissy you are, I thought mother was joking, but she was understating it, wasn’t she? You’re a diaper wetting sissy baby girl and I think it’s just lovely to see, don’t you, mother? No pretence at masculinity, just a surrender of your sexuality and a nice big diaper! You’re almost pretty in that dress, Chrissy, almost a real girl, but not quite and everyone who’s seen you today knows that you’re really a man! So suck your pacifier and we’ll hold your hands while we wait for your Mommy and Auntie!”
For 10 minutes I was made to watch as my wedding dress design was finalised and I was gently teased by my step-sister and her daughter. When Auntie Gemma and Mommy joined us, they looked at me with hungry eyes, telling me that I would look so pathetic in my dress, but that they just wanted me to know that I deserved it. Telling Miss Wei to use my credit card to pay for the clothing, I was soon being wheeled out of the backroom and into the convention hall. It was obvious that the show was wrapping up, as there were very few people left inside and several of the displays were in the process of being taken down.
Auntie Gemma kissed Miss Wei on the cheek and asked her how long until the dresses would be completed. She looked at with a toothy grin and said 2 weeks, as I’d paid extra for speedy delivery, but that the maid of honour, bridesmaids and grooms suit would be finished sooner. They exchanged cards and we were off, back through the room and out into reception. With no delay I was pushed outside and found myself in the back of my van. Auntie Gemma locked the push chair in place and closed the back doors, leaving me on display, as the ladies talked for a while. The group broke up, with hugs all around and waves goodbye to me.
Auntie Gemma got into the front of the van started the engine and turned on the display at my feet. I was looking at a view of Auntie’s panties, straight up her dress and I sobbed at the sight. Her voice came over the speakers and she told me that we’d be off in a minute, but she needed a quick wank. I watched as Auntie Gemma masturbated her fingers a blur and I wanted to spurt so badly. It was over in moments, her orgasm loud and long, as she explained that I’d been such a turn on all afternoon and she’d been dying to come. She pulled away and we headed home, the direct way, but I had no chance of hiding. The whole of the back was light up and in the early evening darkness; I was on display even more than earlier. We pulled on to my drive and were soon inside my house.
“Alone at last, Chrissy and it’s our first night together! What should we do? Maybe a nice evening meal, followed by a movie and an early night! I think that’s just the ticket after such an eventful first day, but first let’s get you bathed and into something more relaxing! Maybe you’ll be willing to help me choose a pretty outfit for me to wear this evening and then you could dress me in it, as well? You’d like that wouldn’t you and I’m willing to let you, but first things first, you need a nice hard caning, don’t you? Don’t be silly, your bottom is aching for my punishment, so let’s have you in your nursery and bare-bottomed for my cane!”
I was rushed along, Auntie Gemma dragging me through the house and into my nursery. I was un-strapped, led over to my cot and ordered to put my face into the mattress. My dress and petticoats were lifted out of the way, my diapers, plastic panties and rhumba panties pulled down around my knees. I looked back at Auntie Gemma, her face a picture of disdain, as she told me that I better not wee-wee while she caned me or that she’d have to tell everyone that I was unable to control myself for 10 minutes without shaming myself. I nodded and she smiled before heading over to the rack of punishment implements, choosing a long, thin cane and returning to stand behind me, slightly to my left. She bought the cane down on my mattress, next to my head, making me jump and displaying just how powerful her blows would be.
Auntie Gemma shushed me, lifted that cane and struck my bottom really hard. I screamed through my pacifier, the shock massive, but I had no chance to recover, as she struck again and I almost passed out. In quick succession, Auntie Gemma gave me 4 more strokes, each harder than the last, until I sank to the floor and sobbed uncontrollably. She left me there for a few minutes, busying herself with things around the nursery and I welcomed the unexpected kindness. She stood over me; I turned and without a trace of shame, licked her shoes. She seemed to be happy at my submission, but soon grew tired, lifting me to my feet and stripping naked with no regard to modesty. I stood in front of her, naked but for my chastity and she giggled, telling me that she loved to see her sissy in all her glory.
“Now then, let’s have you in the bath and clean for our evening, but before that do you need to go potty, Chrissy? You do, well then let’s start with a nice full potty and we’ll go on from there! Now sit down, Chrissy and I’ll hold your hand while you go wee-wee! I hope you understand while Auntie had to cane you, but you were so silly this afternoon for all those ladies and it was clear that you should be punished for your disgraceful display! What do you mean, you didn’t do anything! Your joking aren’t you? You wet yourself, twice and had to have your diapers changed, so don’t pretend that you didn’t misbehave! Now let’s see a nice full potty and we can forget about it all!”
I want wee-wee, as Auntie Gemma looked on and clapped at my performance. She pulled me off my potty and into a warm bubble bath, proceeded to wash me all over, paying particular attention to my chastity device and bottom before pulling me out of the bath. I was dried and powdered all over before being dragged into my nursery. Auntie Gemma pulled me over to the clothing rails and asked me if I saw anything to wear for a girl’s night in. I pointed to a darling babydoll, made of pink glass silk and edged with pink lace. Auntie Gemma held it up and asked me if I was sure, as I’d be unable to hide anything from her in this outfit. I nodded, red faced and she dressed me in the 2 piece outfit without diapers. She laughed when I asked her why I wasn’t being diapered and she told me that I was sweet to want to be diapered, but that I would be using my potty this evening.
She choose a pair of 2” heeled pink fluffy slip shoes and a pair of hold up white nylon stockings. She helped me put them on before she put a pacifier in my mouth, tied behind my head and led me back into the bathroom. She pointed to my potty, told me to clean and dry it before heading to the kitchen to prepare a light meal for her. She would join me in half an hour; I should be waiting for her at the table. I quickly complied and rushed until I was finished with a couple of minutes to spare. I’d prepared a light vegetable risotto and poured her a large glass of red wine. I knelt on the floor next to her chair as she walked in and took my breath away. She was naked, except for a sheer black net, trimmed with satin and a pair of red 6” patent leather stiletto shoes. She was exquisite and when she looked down at me I was lost in her gaze.
She smelt fresh from the bath, as she ate my meal in near silence, only broken by the clink of metal on plate and her appreciative sighs of enjoyment of my food. She finished, reached down, patted me on the head and told me that it was time for my evening meal. She strapped me in an over-sized high chair, my arms strapped down and my body unable to move. She placed a bottle of formula in the microwave, opened several cupboards before pulling a large jar of chocolate spread out and placing it in front of me. Auntie Gemma asked me where my bibs were and I pointed to a pile behind the door. She picked a frilly yellow 1, with a picture of a large duck on the front and tied it around my head. She removed my pacifier, collected my bottle and opened the jar. Using a large metal spoon, Auntie Gemma scooped up a large blob and pushed it into my mouth. About half of it went in but the rest went all over my face.
“What a mess you’re making, Chrissy! You’re clearly a real baby, aren’t you? Not only are you unable to control your bodily functions, but you’re even losing the ability to eat like a grown up and I’m disgusted with you! Sissy baby girls who don’t eat nicely get there bottoms spanked and you’re going to be over knee right after we’re finished here! Now open up and drink all your formula, while I get another glass of wine and take some photo’s to send to Jade! Look over here and smile, Chrissy, your niece will love these shots of you and I hope she shows all her friends! Don’t worry though, as I’m sure she’ll explain that you’re her uncle and well deserving of such treatment! Maybe they’ll be coming to our wedding and you can explain to them that you were spanked for being such a naughty sissy!”
Auntie Gemma took a dozen photo’s, with her phone and emailed them to my niece Jade. She texted back a big smiley face before I was cleaned up, un-strapped and helped down. I was bought over to Auntie Gemma’s chair, laid over her lap and soundly spanked over my see-through knickers. She only gave me 6 smacks, but I was still very sore from earlier caning and I sobbed like a c***d. She pushed me off my lap and pointed at my potty, telling me that I should hurry up and use it before I got to pick out her clothing for this evening. I went quickly, the shame not so much, as Auntie Gemma looked on and glared. I was ordered to take the full potty to my bathroom, empty it, clean it and then join her in her bedroom.
5 minutes later I was knocking on her bedroom door, my former bedroom door, and my potty in hand and waiting for her permission to enter. Auntie Gemma called through the door and I entered her bedroom, knelt before her and waited for instruction. She removed my pacifier, asked me to stand and choose her lingerie for the evening. I looked at her open-mouthed and begged her not to change a single thing, that she looked stunning and it would be my honour to have her by my side in such a fabulous outfit. She bent over and kissed me on the lips, her tongue darting in my mouth, briefly and caressing my tongue. She lifted my face in her hands, looked me in the eye and smiled.
“Very good choice, Chrissy, as I love being almost completely naked in front of you, knowing that you can’t do anything about it and teasing you remorselessly, it’s just so much fun! Now how about heading downstairs and watching a movie together. I’ve chosen 1 that I think you’ll love; it’s called Sissifaction and Humiliation! It’s all about a naughty young man who’s dressed up like a French maid by his mistress and made to do some very nasty things! It star’s a very lovely lady called Maitresse Madeline and I think you’re partial to her, aren’t you? Yes, let’s head downstairs and watch this on the big screen, while you sort my dirty lingerie, for washing afterwards! Here you are my used panties, bra’s and everything else, ready for your inspection and handling!”
Auntie Gemma passed me a large bag, over flowing with her unwashed lingerie and took my potty from me. She headed out of the room and I followed close behind, being treated to the view of her magnificent behind, through her sheer peignoir. She looked back and told me that I should feel free to gaze at her bottom, like a pervert, as she wanted me to know just what I’d never have, even after we were married. I looked at her with unashamed desire and she glowered at my desire. We entered my home cinema, the massive 80” ultra hd screen at the front of the room and I was ordered to connect to the web. She took the tablet off me that controlled the set up and bought up the site Divinebitches. I was already a member, so in seconds we were watching the film and I was in heaven.
Auntie Gemma had me sitting beside her, cuddling her and with my head resting on her shoulder. She reached down, inside my knickers and stroked my chastity covered cock. She licked my ear and asked me if I had seen this before, I nodded and she whispered that she thought so and had I spurted to it before. I nodded again and she seemed unsurprised telling me that those days were long gone and I could expect only humiliation from now on. Auntie Gemma pointed to her dirty lingerie and asked me if I expected them to sort themselves out. I sank to the floor, opened the bag and bought them, ashamedly, to my face and sniffed the open bag. I glanced back at Auntie Gemma and she just smiled at me, so I buried my face deep inside and inhaled every aroma.
I admit it, I am a dirty little sissy pantie sniffer and long may I be 1. I started lifting out each piece of lingerie, with reverence and love, glancing back at Auntie Gemma for guidance, but she’d become engrossed in the movie. Her hand was slowly rubbing her pussy, her legs wide open and resting on the arms of the chair. I was torn between watching her masturbate or worshiping her dirty lingerie and like the sissy I am, I embraced my perverted side and sniffed, licked and folded every item. In fact it didn’t even register when the movie finished and Auntie Gemma turned her attention to me. She asked me if I’d almost finished my task, as she wanted me to help her get off, as the movie had finished to soon and she wanted to orgasm. I looked at her, as she reached down and removed my pacifier. She pointed to my stack of her lingerie and ordered me to pick my favourite item. I picked a pair of her used knickers, full cut and red silk.
“Like them, Chrissy, well why don’t you put on a little show for me? Pull down your knickers and put mine on, go on, put your Auntie’s knickers like a good sissy! That’s so much better honey; you look like a real femboy now, imagine dressing in your future wife’s knickers and right in front of her as well! Tell you what why don’t you suck on some of my used tights, the crotch area, where my pussy and bum were, go on do it sissy! That’s a good girl, lick Auntie Gemma’s tights and I’ll just wank! You make me so wet you know, wetter than any of my boyfriend’s ever have, but it’s not because of your cock, you know? It’s because your just so wanton and depraved, aren’t you? Pull your chastity covered cock out of my knickers and rub 1 of my bra’s over your balls, that’s it, show me how much you worship my lingerie and I’ll let you kiss my bottom, like a real slut!”
Auntie Gemma exploded in orgasm, as I stood in front of her, caressing her dirty lingerie all over my body and showing her that I am hers utterly. She told me to finish sorting her lingerie, while she flicked through other movies on Divinebitches. I was soon finished and asked Auntie Gemma for permission to hand wash her lingerie and with a barely intelligent grunt, I curtsied and left the room. I headed for the laundry room and its massive gleaming sink, more than big enough for all of Auntie Gemma’s lingerie. I entered the room, placed the sorted pieces of lingerie on the counter and turned on the hot water taps. I wanted warm water, not too hot, as the fabrics were delicate and I didn’t want to damage them. I soon had a sink full of warm soapy water and was happily hand washing Auntie Gemma’s lingerie when she entered, stood behind me and rubbed my bottom.
I’d changed out of her lovely knickers and was once again wearing the matching pink pair of glass silk knickers belonging to my baby doll. She licked my earlobe and continued her gentle caress of my bottom while I pretended not to be completely turned on by the closeness of her. She whispered in my ear that I was doing a good job with her lingerie and I should be proud of my ability to care for such beautiful items. She kissed my shoulder, as she reached inside my knickers and very lightly tickled my bum, making me shiver at her intimate touch. She asked me if I liked it when she tickled my hole and I told her that it was very nice, she laughed and told me that all sissy loved it up the bum. She was teasing me, making me tremble with desire for her, all the time I was cleaning her lingerie and that was the point. She was attempting to make associate sexual pleasure with the act of cleaning her lingerie.
She asked me if I needed to go potty and I nodded, red faced and embarrassed at her question. I was still ashamed of using my potty in front of her and she knew it, taking every chance to further my degradation to her. She pointed to the floor and I knelt down in front of her, my eyes catching her as she asked me to wait there while she fetched my potty. I was still there when she returned and soon found myself sitting on the plastic monstrosity, my knickers around my ankles and my hand in hers. She stroked my face and told me that I was her naughty little sissy girl, she asked me to go wee-wee for my Auntie and I did.
“That’s a good girl, Chrissy, make wee-wee for Auntie and you can kiss my bottom, like I promised earlier! On the cheek and on your potty behind me, like a darling sissy baby girl and don’t think I won’t love it! You’re a very lucky girl, to get the chance to touch my flesh with yours and you should beg me to spank you for the privilege! That’s what I like to hear no fill your potty, that’s it and now for your treat! Pucker up, Chrissy and kiss Auntie Gemma’s left buttock and now the other 1, good girl!”
The following 2 weeks, leading up to mine and Auntie Gemma’s wedding, was a series of humiliations and frantic organisation. Mommy had decided that the ceremony and the following reception should take place at my house, utilising the large back garden and the erection of a large tent. The event would be officiated over by a friend of Mommy’s who was willing to accept such a strange situation. Caterer’s from out of town would set up the food, buffet style and then leave us to our fetish wedding, no the wiser. About 30 guests had been invited and I had little say, other paying for everything though. My days were filled with the constant teasing and degradations, at the hands of my tormentors.
My mornings started with Auntie Gemma waking me up in my cot, my diapers soaking and in desperate need of a change. With a smile on her face and without any sense of delay, she’d have me stripped and cleaned. I’d be naked in front of her, but for my chastity device and she’d take great pleasure in verbally humiliating me. Her favourite then was my total inability to go through the night without wetting myself and she’d ask me if I was doing it on purpose. I tried to explain that I couldn’t help it, but she’d just laugh at my attempts to apologise. Auntie Gemma would lead me over to my gyno table, strap me in, my legs spread in the stirrups and give me a massive soapy enema.
“Time for Chrissy’s enema and we both know how much you love the feeling of your cock nozzle in bum, so open wide and I’ll fill up your waiting hole! That’s a good girl, your Auntie loves to see you take every inch of this monster and maybe if you beg me to fuck your sissy bottom, I’ll wear your favourite apron for morning feeding time! The special 1 that you got me, with the holes for bottles and made of very soft rubber, so any spills can be easily wiped away! No, that’s not good enough, sissy really tell me just how much you want this cock up your bum, in a loud lisping voice and I’ll fuck you properly! Much better, Chrissy, so here comes the cock, all lubed and stiff!”
Auntie Gemma slowly pushed my cock nozzle, up my bum, taking great pleasure in my sighs of titillation and asked me if I loved being filled up. I nodded at her direct question and she told me that I was total slut. She commenced with a hard, fast, fucking of my bottom, all the while she tickled my balls and called me names. I was dripping like a faucet, my spunk all over my thighs and the table. She stopped suddenly, just as I was about to reach some kind of release and she opened the tap, letting the warm soapy water enter my bowels. My first enema had been erotic, even tender, but this was matter of fact, as I was left to take every drop of that liquid, while Auntie Gemma ran my bath and laid out my clothes.
When every drop was inside of me, she unstrapped me, helped me over to my plastic potty and watched as I emptied the foul smelling water into the receptacle. I was made to carry it into the bathroom, clean the potty and stand for a hosing down before entering the bubble bath. I was soon being scrubbed by my near naked Auntie, her hands caressing all my most sensitive places and I asked her if she was cross with me, as she seemed distracted. She squeezed my thigh and told me not to be so silly; she was just thinking what we could get up to today. She asked me if I would enjoy a little shopping trip, to find her some lingerie for our wedding day and I looked at her with chagrin. I was to be publically displayed once again and she seemed not to care.
“Of course I care, Chrissy, I care very much that you should be exhibited, around town, for as many people to see as possible and I’ll love every moment of your humiliation! Don’t cry, you’ll be the frilliest little sissy baby girl in town and I bet everyone will think so, too! You’ll just have to grin and bare it though, as I make the rules around her and you obey, don’t you? Now I’ll just check your bottom for any lingering mess, get on all fours and I’ll push a couple of fingers inside! That’s a perfect sight for a sissy’s Auntie, her baby girl accepting her fingers like a champ and being all squiffy about it!”
Auntie Gemma fingered me for a while, humming a tune under her breath and making me into her finger puppet. When she dragged me out of my bath and towelled me dry, I was the happiest little sissy baby girl in the world. She wasted no time in dragging me into my nursery, putting me in 3 pairs of massive lemon diapers and pinning me up. She pulled a pair of opaque plastic panties up my legs, tucked the diapers inside and lifted me to my feet. She had me half way through the house, dressed like this, as she explained that she’d finish my dressing after my breakfast. I was in the kitchen in moments, Auntie Gemma headed out of the door telling me to make her breakfast while she dressed.
20 minutes later she returned, dressed in a 1950’s style red chiffon dress, ankle length, with petticoats at the hem and sheer black silk stockings on her legs. She tottered on 5” black stiletto heels and wore her hair up. Around her long neck was a long string of shiny pearls and she looked like a housewife from an old Hollywood movie. I gasped at her appearance and she twirled like a little girl, asking me if I liked what I saw. I told her that she was mesmerising and she smiled before giving me a big hug. Auntie Gemma towered over me and my face was at the level of her breasts, so I was treated to a face full of perfumed cleavage. She released me and I served her bacon and eggs. She ate, daintily, looking at with her deep soulful eyes and asked me if I was hungry. I nodded and she told me that I’d soon have a very full belly.
She finished her meal, put 2 bottles of my formula in the microwave to warm and put on that totally ridiculous feeding apron. She fitted the bottles to the apron, led me into the living room and on to her lap. Auntie Gemma presented me with a rubber teat and I opened wide, sucking down all that warm goodness. She smacked my thighs, very hard and told me to hurry up, as she’d spank me until I finished my meal. I was beaten remorselessly, as I fed and I sobbed at the shame of it all. She wouldn’t even allow me access to the second bottle until I told her that I wanted another enema, this evening before bed, as I was a very naughty girl. She giggled and promised me a very big enema before letting me start on the second bottle.
“I do so love to spank you, Chrissy and have you wriggle on my lap, your legs kicking and your eyes watering! Auntie knows best and you need some very sore thighs, for our outing, to remind you whose boss! Now, I think 6 more and you’ll be well set, so wriggle for me, Chrissy and it will soon be over! That’s a good girl, bawl like a 2 year old and show me just how pathetic you truly are! You can’t even handle a little spanking without showing me you’re a loser and I want you to know that I’m disgusted with your display, this morning and I expect you to be contrite afterwards, so on to your knees and lick my shoes, like a good sissy!”
After that dreadful beating, I had no chance to recover, as I knelt in front of Auntie Gemma and licked her shiny shoes. I was afforded a view right up her skirt and petticoat, to her stocking tops and beyond. She patted me on the head, tenderly and slowly lifted the hem of her dress, showing me her black silk French knickers. She told me that I was a nasty little pervert for looking up a ladies dress and that I should be ashamed, but she continued her display. She was teasing me, making me desire her, and all the while telling me that I was naughty for doing it and shaming me for my feelings. I was unable to look away, as she pointed out all the lace on the leg holes and told me that they tickled her thighs.
I asked her about her petticoat, wondering why she was wearing such an obviously sissy item of apparel and becoming tongue tied at her glare. She told me that in the 1950’s, most well to do women wore petticoat’s and only since then had frilly little sissy like me had co-opted the clothing. She dropped her dress, stood up and told me that it was time for my dressing. She led me to my nursery, sat me at my vanity and handed me a pair of very frilly lemon silk knickers, with white lace ruffles on the bottom and a phrase on the front. It read “AUNTIE’S DIAPER SLAVE” and she held them open for me to step into. I was once again dressed in the most feminine and shameful of knickers, by my Auntie and she laughed at my reticence. She asked me if I thought that they were pretty enough for a big pansy like me or should she pick a different pair. I simpered and told her that they were very lovely and would she please allow me to wear them for her.
I stepped inside those frilly knickers and lost myself in the feeling of silk and lace. She secured my knickers in place, tucking my diapers and plastic panties beneath them before passing me a pair of white silk and lace ankle socks. I sat down, pulled them on my feet and waited for my shoes. They were tiny silk ballet slippers, lemon once again and I tied them onto my feet. Next was a very frilly bra, white with lemon lace and stuffed with Auntie’s dirty tights. She helped me with my bra, teasing my nipples and snapping the strap at the back before pointing at my petticoat. Unlike her sophisticated thing, mine was short, massive and covered in tiny lemon bows. Yards of very stiff netting gave it body and when I stepped into it and she tied it around my waist I almost fainted with feelings it produced in me. She reached under my petticoat and rubbed my bottom, possessively.
“I love to see my sissy fiancé, in his petticoat and ready for his pretty dress, all girlish and ready to play! So let’s have you stood in front of me, arms up and I’ll lower it onto your waiting body! Not many boys get to dress in such darling clothes, but you’re a special case, aren’t you? You need to be dressed like a little girl and Auntie Gemma will always oblige your naughty desires! Isn’t it lovely, Chrissy and it’s just for you! I bet the ladies in the lingerie shop have never seen such girly dress and they’ll be shocked when they realise a boy is wearing it, but I’ll be sure to tell them that it’s alright, as you can’t help being a pervert! Now arms down and I’ll do up the buttons, smooth the dress and give you a lovely hug!”
I was engulfed in her embrace, the feeling of the dress and petticoat making me totally submissive to her desires and wants. She pulled me over to the floor length mirror, presented me and giggled at the look on my face. I was just so frilly and when she told me that I was ready for my make up, I begged her to give me a very sissy look. She told me that she knew just the 1 and after 10 minutes of work she had me check it out. She’d made me look like a doll, my face white and my cheeks blushing red, with a small lipsticked pout, I was horrified. She laughed at my shock, telling me that I’d asked for this and maybe I should have thought about exactly how I’d be humiliated by her. She picked up a pair of white lace fingerless gloves, had me put them on and told me that all little girls needed to wear a hat when they left their houses.
She placed a small straw boater hat on my head, a lemon ribbon around the body and pinned it to my wig. Auntie Gemma giggled and told me that I looked like a real 1950’s little girl, that I was perfect for our shopping trip and that it was time to go. I was led to her bedroom, where she put on a pair of white leather gloves and a black wool calf length coat before picking up my diaper bag. We headed downstairs, to the cloakroom, where she had me put on a clear plastic Mack, with ducks on the front and strapped me into my push chair.
20 minutes later, we were pulling up outside the lingerie shop, on the high street and I was petrified. The journey had been traumatic, but what was about to happen was much worse, as Auntie Gemma took ages to get out of the front of the and get me out. A small crowd had formed, about a dozen women and c***dren, as well as a few men. When I was left on the pavement, as Auntie Gemma locked up the van, 1 of the c***dren approached me and lifted up my dress, pointed at my diapers and told her Mother what I was wearing. The crowd seemed appalled at my display and I wanted the ground to swallow me up, as the young girl asked why a grown man was wearing diapers and a dress. Auntie Gemma grinned at me before addressing the hostile group.
“Chrissy has been a very naughty boy and pretended for years that he was a real man, so when I found out that he was a big fibber, I decided to punish him for being a liar! This sissy gets to wet his diapers all the time now and use a lovely potty when were at home! Dressing like a little girl is totally humiliating for him, but that’s what he deserves, doesn’t he, everyone? See Chrissy, all the nice people agree that you deserve to be dressed like a little girl, but maybe I should tell them about how much you begged me to petticoat you today and how you cried when I told you that I wouldn’t do it! Chrissy cried and begged so much that I relented, so let me show you his frilly petticoat and his darling knickers underneath, as well! Oh my, have you wet yourself darling, well I had better get you inside and change your dirty diaper, hadn’t I? Wave goodbye to your new friends and let’s go lingerie shopping!”
I entered the lingerie shop to a cacophony of laughter, my face bright red and I was sobbing softly, in shame. Auntie Gemma whispered in my ear, that I’d been very good and I should be happy that I’d brightened the day for so many strangers. After all, she remarked, laughter was the best medicine and I’d made such a spectacle of myself that they’d be giggling for days. I looked at her with despair, as I was pushed through the displays of lingerie and parked at the desk near the back of the store. Standing there was a smiling young lady, perhaps 25 and well dressed. She came and stood in front of me, her breasts peeking out of the low white cashmere top she wore, letting me see her pink silk and lace bra. Her white silk stocking covered legs were finished off with a pair of pink 5” stiletto heels and she wore a short pleated skirt as well.
She asked Auntie Gemma just what I was wearing and she told her, in a very prim and proper voice, that I was her diapered sissy baby girl. The young lady, who I learned later was called Sonya, giggled and asked me if was alright, as she dabbed at my tear filled eyes. Auntie told her that I was crying because I’d wet my diapers and all the people outside had seen my shameful antics. Sonya lifted my petticoat and dress, checking my diaper and my wetting was obvious. She rubbed the front of my diaper and told me in a very strict voice that I was extremely naughty and that I should be guilty about my shameful diaper wetting. Auntie Gemma asked Sonya if there was somewhere she could change my diaper and would she like to observe or even do it instead.
Pointing to an open door, she told her to feel free to use the space and that she’d love to watch but thought it was a bit much to change a strange man’s dirty diaper 2 minutes after meeting him. Auntie Gemma told her that I loved to be changed by strangers, in fact she should feel free to spank my bottom for my crimes and I’d be grateful for her chastisement. I was wheeled inside, unstrapped and laid down on my changing mat. Sonya lifted my petticoat and dress out of the way, took my ankles in 1 hand and pulled down my soaking diapers. She squealed in surprise when she spotted my chastity covered cock and asked Auntie what I’d done to deserve such harsh treatment.
“To be honest, Sonya, we decided that, Chrissy here didn’t deserve the right to spurt like a real man, so we locked away his cock and made him suffer for his nasty perversions! Now he has the pleasure of wearing pretty dresses instead and wetting his diapers like a little girl, but he prefers it to spunking, don’t you, sissy? See he’s open about just what a dirty boy he was and what a good girl he wants to become, aren’t you? Now tell the nice young lady why we’ve come here today! That’s right were getting married in 2 weeks and I need some very special lingerie to wear under my tuxedo, don’t I? See my intended is going to be the 1 wearing a wedding dress and I’ll be the groom, right until the wedding night when I’ll be underneath a real man, getting fucked and he’ll be in his cot wetting his diapers and listening to me scream in satisfaction!”
Sonya laughed at me, as I was humiliated once again by my Auntie and made to feel tiny. She passed my bottom cleaner, some baby wipes, baby oil and powder, getting in return my dirty diaper. I was cleaned powdered and diapered quickly before having a pair of dry opaque plastic panties pulled up my legs and over my diapers. Next was a pair of bright pink sheer glass silk knickers, covered in white lace and dripping with long ribbons. I was helped up, made to step into those waiting knickers and once again I stood there in disgrace as a strange woman made me quiver in horror. She caressed my newly diapered behind and asked me if I liked my new knickers. I sniffled and told her they were very pretty before thanking her for changing my dirty diaper. So told me that it was her pleasure and stroked my throbbing thigh tops.
She asked Auntie Gemma about the red marks and she had me explain my spanking earlier. Sonya looked me in the eye and quietly told me that she was going to smack my thighs now. I looked over to Auntie Gemma, she smiled at me and I was led over to a small desk before being bent over, my bum in the air and smacked 20 times by Sonya. I’d been spanked harder but the earlier humiliations along with the damage done by Auntie Gemma soon had me hopping in agony. When it was over, I fell to the floor and kissed Sonya’s shoes in gratitude. She seemed surprised at my actions and my Auntie told her that I was thanking her like a sissy. She bent down and lifted me up telling me that I needn’t bother, as it had been distinct pleasure to punish my well deserving bottom.
We headed back out to the shop, proper and began to peruse the lingerie. Auntie Gemma picked out dozens of pieces, passing them to me, to hold and I soon looked like a mountain of silk and lace. Sonya asked if she wanted them all and she explained that I bought all her lingerie. I lisped that what Auntie wanted, I bought and it was my only wish that she would allow me to see her wearing such gorgeous lingerie. Sonya seemed surprised that I was allowed such intimate viewing of my Auntie, but she reminded her that I was locked away and unable to become sexually aroused. In fact I was the perfect person to see her in a state of undress or partially clothed as I had great taste in lingerie. Auntie Gemma told me to put her lingerie down beside the tills and re-join them presently. They were sitting side by side, on a small sofa, their legs spread and the skirts raised. I knelt in front of them and stared.
“Aren’t Sonya’s pantie’s pretty, sissy? There so very girly and I bet you’d love to try them on in front of us, pretending you’re a real girl and not a diaper wearing sissy baby, but you can’t! You can’t, because you’re disgusting, aren’t you? Chrissy is a nasty little pervert, Sonya and I bet you’d like to hear all about his licking of my dirty lingerie before he hand washes them and I spank his bottom, for shame! I’ve been trying to potty train, Chrissy, haven’t I, but you love to wet your diapers so much, that I have to keep him secured when we’re out and about! No he doesn’t p*o in his diapers, because of the bowel cleansing enema that he begs for each morning and I’m very strict about them, aren’t I? Chrissy has a very special penis shaped nozzle, which I lube up and force up his bottom, over and over again, till I reach the root and fill up his bowels with soapy water! You should see his cock dribble when I push it in, I laugh at the site, but he loves it and I do love to give him a little fun!”
I was gaping, opened mouthed, at Auntie Gemma, as she made me seem like I needed such wicked and disgusting treatment, at the hands of my Auntie, but when she reached down and kissed me on the lips, I just melted. I stared up at Sonya and told her, in a very girly voice, that I loved Auntie Gemma’s big cock in my bum and needed her enema’s because I’m unable to control myself. She looked at me with derision, as she asked me if I would really p*o my diapers and I just nodded, my face bright red and my eyes full of tears. I begged her not to laugh, but she smiled, as I told her that messing my diaper was so sexy and made me feel horny. She looked at Auntie Gemma and told her that she must be mad to consider marrying a loser like me.
She giggled and explained that I was rich, very rich and she would be getting access to half of my vast fortune. I told her that I was happy to be used by my Auntie and if she got any kind of pleasure from my disgusting behaviour, I was so proud. Sonya was slowly masturbating, as my Auntie and I, explained our kinky unconventional relationship and when I looked at her hand inside her panties, I knew that I had the power to turn on women with my humiliating displays. For a sissy to have that kind of control over a beautiful woman was mesmerising and I took the opportunity to test just how far I could go. I looked at Auntie Gemma and told her that I wanted her to fuck a real man, in my cot, on our wedding night, while I lay next to them and sucked on a penis shaped pacifier.
Auntie Gemma asked me if I was joking, I shook my head and told her that I would like her to fuck a real man, right next to me, on our wedding night and it could be her wedding present to me. Sonya was masturbating harder and deeper, as I looked at my future wife and begged her to cuckold me, intimately and blatantly. I begged her to allow me the privilege of observing how a real man could satisfy my wife, in ways I couldn’t and would she make me tell him, when it was over, that I was happy that he had spurted in her and could I please sniff her spunk filled pussy. Sonya appeared to be close to orgasm and when Auntie Gemma replied to my request, it drove her over the edge and deep into a massive climax.
“I’d be more than happy to fuck a real man, next to you, Chrissy and I’ll be sure to have you sniff my spunk filled pussy, but why don’t we go the whole hog and invite and audience to our marriage consummation, as well! How about your step-sister, Jenny and her daughter, Jade? I’m certain they’d love to witness just how much I love and honour our commitment, as you wet your diaper and I suck a large hard cock, but do you think we should ask Sonya if she’d like to be there, hmm? Would you, Sonya? Would you like to watch Chrissy’s face as I fuck a well hung man, bent over his cot, my arse in the air and screaming in ecstasy, as I’m defiled by a stranger? I bet you’d masturbate, just like you’re doing right at this moment and you’d be right to! I mean you’re a dirty little bitch, aren’t you? Wanking off to a pair of kinky strangers, in the middle of an open shop, where anyone could walk in and you don’t give a fuck, do you? Ejaculate for me, Sonya!”
Loudly and with vigour, Sonya obeyed my Auntie Gemma and orgasmed right in front of me. I was looking up her skirt, her legs spread and her fingers deep inside her sex. I looked at my Auntie and told her that I loved making women orgasm by humiliating myself and could I please be allowed to suck Sonya’s stiletto heels, as a special treat. Auntie Gemma nodded and I knelt down, took her left stiletto heel in to my mouth and sucked it like a cock. I became lost in that deeply erotic submissive act, as I abased myself and I loved every moment. I was so aroused and was unable to express myself in no other way than to wet my diaper, so I let go and in seconds my clean diapers were once again full of my urine. With no regard to me or my situation Auntie Gemma pointed out my disgraceful act to Sonya, but I was beyond caring, as I deep throated that long thin stiletto and licked every millimetre.
I was allowed to abase myself for several minutes as Sonya came down from her post orgasm high and chatted to Auntie Gemma. The conversation centred on just how much I’d turned Sonya on and was this all for real. With a flourish Auntie Gemma explained that every day with me was a battle of tease and denial of the most basic of control over my life. Locking me away in chastity, stopping me from orgasming, having me use a diaper and a potty had made me into a sexual object of epic derision. In fact, she said, I was so in need of this, that I would do just about anything for a simple touch of human contact. She had me stand and gave me a hug, cooing softly that I was a very good sissy and I had done very well, but that I didn’t deserve having my diaper changed so soon and that I would have to wait until we got home.
I was ordered to help the ladies straighten their clothing and in particular there lingerie before being dragged over to the till. I used my credit card to pay for the masses of lingerie that Auntie Gemma had picked out and thanked Sonya for allowing me to enter her store. She told me that I was welcome and should feel free to return, especially if I spent as much money next time. Auntie Gemma and I headed out to the waiting van, I was strapped in and we headed home, our morning’s adventure complete and my diaper soaking.
We arrived home to find Jade waiting in her car and she was soon bounding out before heading over to greet Auntie Gemma. They hugged and chatted for a few moments before walking over to the back of the van. Jade opened the door and said hello, to which I was unable to return because of the penis shaped pacifier buried deep in my mouth and tied around my neck. I moaned through the pacifier though and Jade seemed to get the point as she entered and kissed me on the cheek. She rubbed the front of my diaper covered crotch and whispered in my ear that she loved to see me suck my pacifier like a good little girl. I shivered at her touch and when she stroked my cheek tenderly, I whimpered. Jade kissed me, high on my forehead and then on both of my cheeks allowing me to breathe in the heady scent of her perfume. I was treated to a close up view of Jade’s breasts, as she bent down and I peeked down the front of her blouse.
“Hello my darling sissy uncle, I’m here to spend the afternoon with you and your Auntie Gemma, won’t that be fun? We’ll be playing some very kinky games, Chrissy, so I hope you’re ready to play and maybe I’ll give you a treat later! Would you like it if I let you kiss the seams of my stockings, all the way up to my garter belt and under my skirt? The only thing is though, I forgot to put any panties on this morning and you’ll be able to see everything, but I’m sure that Auntie Gemma would supervise your actions and if she thinks you’re taking liberties with my person, she’ll be quick to punish you! Maybe I’ll even watch, as she smack’s your naughty bottom and I’ll grin at your distress! Your bum will be all red, almost as red as your sissy cheeks, as your young niece observes your shameful punishment and be sure to think about me telling my Mother all about it, as well! She’ll be mortified that I was privy to your perversions!”
I whimpered in shameful embarrassment, as my young niece, took every ounce of pleasure from my desires, all the while my Auntie Gemma looked on and smiled at my red face. She strode over, took my hand in hers and asked me if I’d like to kiss my niece’s stocking seams. I nodded and she sighed at my response before turning to Jade, remarking that I was incorrigible. Jade rubbed the front of my diaper and whispered in my ear that she thought I was very sexy in my pretty dress. I stared at her and she smiled. Jade whispered that diapers were perfect for a bottom as girly as mine and the fact that I was unable to control myself in them on confirmed the fact that I was pathetic. She looked up and in a clear voice asked Auntie Gemma if she thought I was pathetic, as well.
Sternly, she looked me squarely in the eyes and told me that she’d never met anyone quite so pathetic and I should be ashamed of myself. I let go of my bladder, as they laughed at their own joke, but I knew they were correct, I am pathetic and need to be reminded constantly. Auntie Gemma took hold of my pushchair’s handles and led her younger friend inside our home, straight into my adult nursery. With a gasp of surprise, my young niece, tried to take in every item of clothing, furniture and equipment at once. She seemed on overload, as she asked Auntie Gemma about item after item and when I was wheeled over to my changing table, she was open mouthed at the design of it.
I was unstrapped and helped out of my dress and petticoats before being helped up, onto the changing table and laid on my back, my legs in the air, as Auntie Gemma held them by my ankles. She turned to Jade and asked her if she’d like to change my dirty diaper. Jade grinned and told her that maybe she’d better ask me if that would be alright, but Auntie Gemma replied that I was not able to involve myself in such important matters like who changed my diaper. She winked at me and told Jade, while staring deeply into my tear filled eyes, that she decided everything about my life now and I should just lay back and accept the truth. That I was a nasty little sissy baby girl and needed her to humiliate me. Jade began to remove my plastic panties and soaking diaper.
“You’ve got it made, Uncle, a woman who wants nothing more than to ridicule and humiliate you, while clearly wanting nothing more than to fuck real men in your former bed! She’ll take plenty of cock, no doubt, but it won’t be this tiny thing, will it? It’s so remarkable to find a man willing to admit just how much he wants to be owned and abused by the women in his life, but you’re special, aren’t you? So very special and when Mother told me all about my sissy uncle, I couldn’t wait to meet you and I wasn’t disappointed 1 bit! Now then lift your behind and I’ll just wipe your sticky bottom before oiling it up and playing with that winking hole between your legs! That’s it open wide for Jade and I’ll make you feel all squiffy!”
With no choice and no hope of my Auntie Gemma stopping her, I was once again violated in the most intimate way and all the time I was verbally humiliated by my tormentor. Jade used a soft, moist baby wipe to clean every inch of my pee soaked behind before cleaning my plastic covered cock and throbbing testicles. She then dropped the wipe and picked up a bottle of baby oil, pouring it over my bottom and her hands. She began a slow sensual massage of my bottom, taking her time, making me sigh in pleasure and giving me a sense of total submission before slowly pushing her middle finger into my hole. With an almost shiver of delight, my young niece violated my body, in front of my Auntie Gemma and I was unable to vocalise any complaint.
I was putty in her hands, quite literally, as she finger fucked my wide open bottom, using first 1 finger and then 2 before I felt her other hand cupping my balls. Her hand was slippery from the baby oil and caressed me with ease, as she pushed and probed my hole with a deep and steady rhythm. Jade looked me in the eye and asked me if I liked having my bum played with. Red faced and cringing at the thought, I nodded and she smiled at me. She told me I was shameless and that I deserved to spend my life in diapers, under the control of strict demanding women, who brooked no nonsense and were prepared to make my life 1 long discipline session.
I whimpered at her assertion and she smiled down at me before pinching my cheek and telling me that I was a darling little sissy girl. She continued her invasion of my bottom, making no effort to spare me the shame of being used this way and even adding a third finger to her frottage. I was nearly burning with humiliation, as Jade made me into her sissy and I looked at her with desire. She stopped suddenly, looked down at me and told me that I didn’t deserve such kind treatment from her. I shook my head, trying to plead through my pacifier, for her not to stop, but she was adamant that I was unworthy of her touch and that she was finished with my hole.
“It’s time for your diaper’s now, Chrissy and don’t pretend you don’t need them, after all you’ve demonstrated a very real need to be pinned inside some lovely soft diapers because you’re a nasty little sissy baby girl! Now don’t cry, pansy, we all know you need this, need the felling of reassurance that you get from wearing your toilet on your body and I’m going to help you realise this! Bottom up and I’ll make you all safe; see that’s so much better isn’t it? No more pretending to be a big man, just a sissy, in her diapers and dressed in a pretty dress! How about these plastic panties, aren’t they just gorgeous? All soft and translucent, so we can tell when you’ve messed yourself, but don’t worry the elasticated waist and leg holes will keep everything inside! Time to finish off with a lovely pair of baby blue rhumba panties, dripping with lace and ribbons, with the phrase SISSY in big letters on the front! Perfect for a sissy baby girl, like you!”
I was pulled to my feet before Jade lifted my dress and petticoats, displaying my diapers and panties to Auntie Gemma. She asked her if she liked my bottom in these and with a viscous grin, Auntie Gemma nodded. She asked Jade if I needed a new outfit for her visit and she beamed, telling us both that she longed to pick out a very special outfit for her visit. I looked at her with longing, as she reached down and ruffled my diaper covered bottom. I was in her thrall, but when she reached inside my diaper and tickled my hole with her finger, I was putty in her hands. While Auntie Gemma stripped me of my outfit, leaving me standing there in just my diapers, plastic panties and rhumba panties, Jade was going through my dresses like a woman possessed.
She pulled out outfit, after outfit, making me stand in front of her as she checked how I looked in them by dr****g them over me and tutting at their unsuitability. This went on for some minutes before she found what she was looking for. Made of white bridal silk and edged in baby blue lace, it was incredibly short. The sleeves were made of gossamer thin white glass silk and poofed up dramatically. There was a small baby blue silk apron perched on the front and a huge lacy sash around the waist. I was helped into it by Auntie Gemma, while Jade picked out a massive white tulle petticoat, passing it over and grinning as I stepped into it. My diapers were clearly visible, but that wasn’t the end of my costume and Jade passed over the next couple of items.
A baby blue silk and white lace garter belt, with white silk seamed stockings followed. Auntie Gemma helped me on with the garter before sitting me down to roll up the stockings and attach them to the waiting garter tabs. Next was a pair of cute baby blue little girl socks and some black Mary Jane’s. I stood up as Jade approached with a massive white silk baby bonnet, edged in baby blue lace and tied on my head with a massive bow under my chin. Finally, she produced a pair of white lace fingerless gloves, pulling them over my hands, making me into the perfect sissy baby maid.
“You look scrumptious, Chrissy, just perfect to serve a group of young ladies afternoon tea! Now get your diapered behind downstairs and into that kitchen and prepare tea for half a dozen ladies! That’s right, Chrissy, we’re expect guests any moment and you should be prepared to show off your darling outfit to several of my closest friends! Here, let me remove your pacifier and you’ll be able to answer any questions they have, about your predicament. Go on we’ll be waiting for you in the living room, so quit your dawdling and follow my orders, sissy!”
I headed downstairs, to the sound of giggling and headed to the kitchen, my heart pounding, my hands sweating, but with no way to refuse and no wish to. As much as I was dreading my public humiliation, I craved the feeling at the same time and I shuddered in shame. As I prepared the tea, I heard the front door bell and my niece’s footstep’s clacking down the hall before the door opening. Several female voices echoed in greeting and Jade said hello to all of them before steering them into the living room, to await my arrival.
The tea was brewed, the tray readied and an assortment of biscuits prepared, when Auntie Gemma joined me. She looked over my efforts and declared then satisfactory, but remarking that she expected a better standard in future. She took my gloved hand, squeezed and asked me if I was ready. I nodded, but she looked at me with pity in her eyes and asked me if my seams were straight. With shake of my head, asked her to please check and bent over at the waist. Auntie Gemma was straightening my stockings as the kitchen door opened and Jade, along with her young friends, entered. I looked back and spied 4 young ladies with grins on their faces, taking in my display.
“Here you go girls, just as I promised my dirty little sissy uncle, Chrissy! Say hello to the girl’s, Chrissy, don’t be shy, they won’t bite, but they might just laugh a little! Girls this is Chrissy! Chrissy these are my friends, Rachael, Abby, Fearne and Jessie! They’ve been dying to meet you since I told them all about you! Give them a nice curtsey in greeting and introduce yourself. That’s a good sissy, show just how under the thumb you are and abase yourself in front of my girlfriends! Check out Chrissy’s diapers, girls! Aren’t they just huge and the little fairy makes use of them all the time! A total diaper wetter, aren’t you Chrissy?”
I sobbed, whispered in the affirmative and curtsied to the 4 laughing young ladies. The first, Rachael, a tall leggy blonde, dressed in a short, tight red dress and black patent stiletto heels, took my hand in hers and shook it like a normal greeting. I looked at her in hope, right until she told everyone how much she loved to see a sissy in such a pretty dress and petticoats. In fact she lifted my dress and petticoats, rustling them before asking me if I loved such frilly undies. I nodded yes and she smiled, telling me that I was b**stly and deserved a life in diapers.
The second, Abby, was another tall leggy blonde, but that is where the similarities ended, as this was a world class looker and she knew it. Dressed in thigh high stiletto boots, made from shiny red latex and wearing a tight black rubber skirt, with a see-through white silk blouse and no bra underneath, she was the essence of sexual desire. She took my chin in her well-manicured hand, lifted my face to hers and looked me in the eyes. In a sultry voice, she asked me if I was attracted to her and I gulped before telling her that any man would be. She laughed and in a cruel tone told me that I wasn’t a man.
I was silently weeping when the third young lady, Fearne, introduced herself to me. She was a very svelte, hippy type girl with long brown hair and bright pink highlights. She was dressed in normal street clothes except for a pair of massive red patent leather stiletto heels. She looked me up and down, grinned at me and asked me if I would show her my pretty panties. I lifted my dress and petticoats, allowing her access and she pointed out the message on the front of them. She told me they were perfect and I should be honoured to be dressed in such lovely clothes in front of so many ladies. I curtsied in affirmation and she giggled.
The final young lady, Jessie, was another kettle of fish entirely. Dressed like a chav in a tracksuit and trainers, she was dark haired and wide eyed at my display. With a prompt from Jade she stepped closer and asked me if I really used my diaper like a real little girl. I nodded and she asked me who changed me. I told her that any woman, who wanted to, changed my dirty diaper and I was grateful for the attention. She asked why and I explained that I was a virgin, with my cock locked in chastity and no hope of release. She grinned evilly and remarked that all sissy virgins should be locked away forever. In fact she was the first to ask me about my upcoming wedding to Auntie Gemma.
“So I hear you’re getting married soon. In fact, you’ve been lucky enough to catch such a delightful creature, as your Auntie Gemma here and I bet she’s going to make you the sissy bitch, to her domineering wife! Do you understand just how lucky you are, Chrissy, because not many women would put up with such pathetic pansy as you and you should get down on your knees right this minute, thank her for agreeing to become entangled in your perverted desires and beg her to degrade you for the privilege! Go on, does it right this second, in front of us and maybe I won’t spank your bottom! That’s it sissy, show us just how much you need to be controlled by a strict lady and I’ll give you a very special treat later!”
I knelt in front of Auntie Gemma, the 5 young ladies standing around me, as I thanked her for taking me to be her husband and begging her to please make my life 1 long humiliating future. She looked down at me, patted me on the head and asked me if I’d be willing to get married, strapped to a potty, for all the guests to see and not be afraid of using it during the ceremony. Jade burst out laughing before telling me that I’d look divine wearing my wedding dress and I should hope that my public use of a potty would make me into a total sissy baby girl, but I should be sure to have an extra-large enema or I’d be pooing right up on stage. She squatted down, reached under my dress, into the rear of my diapers and caressed my bottom. She whispered that nothing would make her happier than to see me fill a nice big potty with a big pile of p*o and that she’d be filming every second of the ceremony, so I’d be able to check out my shame from her perspective.
Auntie Gemma told me that it was my decision, but I should remember that I was nothing more than a disgusting diaper wearing sissy baby and she thought everyone should have the chance to see just how perverted I was. With tears in my eyes and a catch in my throat, I told her that I’d do anything in my power to please her and if by humiliating myself, I made her day slightly better, I’d do it. The ladies clapped at my agreement and I looked at them with horror as they were obviously delighted with my submission. I asked Auntie Gemma if I could please be allowed to kiss her shoes and she nodded. I licked and kissed her shiny stiletto heels with gusto, sublimating my humiliation in a smaller degrading task.
After a few seconds Abby asked if was ever going to serve tea and that she expected me to be properly humble in my service to them. They drifted back into the living room as I assembled the last few items on to a large try and carried them through. I spent the next 20 minutes serving those 6 ladies a very proper afternoon tea, with biscuits and cakes, while they chatted about everyday things. I’d just served a second cup to Jade, when I felt a hand under my skirt, rubbing my bare flesh above my stocking tops and up to my diapered bottom. It was Fearne and she pulled me down next to her, my petticoats flaring out and my behind crinkling. She took my hand in hers, looked me in the eye and complimented me on a fine repast, but she thought I needed a bare bottomed spanking from her to remind me of my place. I begged her not to, but she told me not to fret and it would soon be over.
“That’s it Chrissy, lay across my lap and I’ll just pull down your panties and diapers! You’ve got a very pretty bottom, sissy, just perfect for being spanked and I’m going to hurt you dreadfully, but you need this, don’t you? Yes you do, Chrissy, you need a hard spanking, so feel free to cry as much as you need, I won’t mind, but maybe the other ladies will think it’s pretty silly for a grown man to cry whilst getting his bum disciplined! I bet they’ll laugh at you and say nasty things, but that’s the price you pay for being a diaper wetter and don’t pretend you don’t love it! You love being the centre of attention, even when you’re being humiliated and ridiculed, so chin up and think of England!”
Fearne began a hard, long and very loud spanking, whilst the ladies looked at me with scorn. In moments I was a blubbering wreck, crying my eyes out and kicking my legs in a frantic attempt to lessen the pain. Abby asked me if I was all right, if she could maybe help me in any way, but when I begged her to help me she just smiled and told me that she was very sorry. She asked me if it was painful and whimpered that it was terrible. She knelt down next to my head, leant in close and kissed me on the cheeks, licking up my tears like a cat licking milk. She told me that a sissy’s tears of pain tasted wonderful and begged me to cry harder for her.
I didn’t have any choice in the matter, though, as Fearne continued her assault on my derriere. Over and over again she smacked my bottom, leaving not 1 inch clear of her ministrations. At the end, I was a mess, my make had run down my cheeks and I was unable to stand without the help of Jade. She re-pinned my diaper and pulled up my rhumba panties before taking my hand and pulling me into a tight hug. I breathed in her lovely perfume and sobbed pitifully, as she stroked my head and told me that it was okay. I settled down after a couple of minutes and she asked me if needed to thank anyone. I looked at her with horror as she nodded towards Fearne, indicating that I should thank her for my spanking and I whimpered at the injustice of my life.
I knelt in front of her and lisped in my most girly, lisping voice, that I was grateful for her punish my naughty bottom so forcibly. I told her that I’d never been spanked as hard before and I begged her to let me kiss the hand that had given me such a painful lesson. She smiled, held out her hand and allowed me to kiss it for a few moments. She looked at me with clear eyes and remarked that I was very lucky to be able to kiss a lady in such an intimate way. She asked me if I’d like to tell her about 1 of my fantasies. I sobbed and begged her not to shame me so, but she was having none of my excuses.
“Tell us you’re most perverted fantasy, Chrissy and I promise we’ll listen to your disgusting desires with all ears! In fact, I’ll even let you sit on my lap while you tell us and rub the front of your diaper! Won’t that be fun, Chrissy? A pretty girl rubbing your diapers, as you humiliate yourself and there’s no way we won’t be appalled at such naughty thoughts, but don’t worry you’ll still be the same girl afterwards, just a little more ashamed! Upsey-daisy, its story time!”
I sat on her lap and she brushed my dress out of the way before reaching under my petticoat and following through on her promise. I was so turned on, but I couldn’t seem to get the words out so she smacked the tops of my thighs and told me she would give me another spanking if I didn’t hurry up. I asked her if she had ever been inside a public toilet at a park and she shuddered before telling me that they were horrible places, full of germs and that she hated going inside them. I told her that I thought the same, but my fantasy takes place in 1. She looked at me with scorn as I explained that Auntie Gemma or 1 of my other caregivers would take me there 1 day, dressed in full sissy baby girl clothing and make me clean every inch of toilets before tying me over 1 of the toilets, pulling down my diapers and exposing my bottom for anyone to use and abuse.
Under full supervision, I would take any abuse meted out, either physical or sexual until she deemed my degradation complete. Jessie asked me if I meant getting fucked in my sissy hole, by strange men’s cocks and I nodded in humiliation. I whimpered that I was so ashamed by my desire to be fucked by a string of anonymous strangers and I was sorry if I offended them. Jade looked at me with a big smile on her face telling me that it was alright and that they understood my need for utter humiliation, but that she didn’t understand 1 point. How was I to clean the toilet?
I stuck out my tongue and licked in demonstration, as I began to cry once again. I begged them to please tell no one about my confession, but they just laughed at my plea. I felt dirty, like I’d bared my soul and been exposed as nothing more than a nasty little sissy baby girl. I sobbed at the injustice of my tormentor’s humiliation of my psyche, as Fearne wiped away my tears and gave me a great big hug. I was stood up and led by my hand across the room and sat down next to Jessie. She looked me up and down before asking me if I’d like my treat now. I nodded and she pulled me backwards over her lap, so I was looking up at her grinning visage. She opened the front of her tracksuit top, her breasts spilling out of her bra and I was captivated. Moments later she opened her bra, at the front and her breasts were free and clear.
“It’s time for Chrissy’s first breastfeeding and I’ve got a nice full pair of tits just for you, sissy! Look at his face girls; it’s a picture, isn’t it! Open wide, Chrissy and prepare for your feeding! That’s it sissy take it, take my milk into your mouth and fill your belly with my essence! I’ve left my little 1 at home with his Father, so you get to feast on my milk and you’re clearly ready for a nice full belly! Don’t pretend that you hate this sissy when I can tell you love every moment of being so intimate with a woman that’s beyond you! Let’s switch you over to my other teat and double up your feed!”
As I breastfed on Jessie’s milk, I was unable to take in the feeling of incredible contentment that washed over me and lost control of my bladder and bowels, filling my diapers with wee and p*o. Jessie sniffed strongly and told the other ladies that I’d messed my diapers. They crowded around me, checking my diaper and giggling at my plight. I could feel their hands all over my diaper covered bottom, squeezing the mess I’d made and I didn’t care 1 iota. The only thing I cared about at that moment was feeding on Jessie’s milk laden breasts.
My wedding day had arrived and I was incredibly nervous. I’d been woken very early, around 6 o’clock, by Jade and given no moment to myself. As I heard the sounds of the caterers and other people preparing for this afternoons festivities, Jade asked me if I’d dirtied my diaper, nodding my head I soon found myself being hauled out of my crib and over to my changing table. Jade sniffed my bottom, grinned through my open legs, down at my face and remarked that I’d be a good girl for not pooing. She asked me if I liked filling my diapers with p*o and answered her own question by remarking that sissy baby girls loved nothing better than messing there diapers. She unfastened my pink baby grow, revealing a massive pair of diapers, covered with translucent plastic panties and set about removing them.
She whistled under her breath, as looked up at her pretty face and took in her appearance. She was dressed in a pale peach silk robe, edged in lace, tied around her waist and very short. Her long legs were displayed and made even tauter by the wearing of peach fluffy slippers, with a 3” heel. Peeking from under the robe was a pair of tiny thong panties, peach silk and utterly divine. I stared at my young niece, with desire, as she changed my dirty diaper and made me feel pathetic. I sucked on my pacifier, until she removed it and asked me a series of questions.
“Well then Chrissy, your big day has finally arrived and I bet you can’t wait to see your lovely dress, but first I want you to answer some questions, truthfully and completely please! First question, sissy, do you know just how much fun we’re all having supervising your total humiliation and is there something you want to say to me?”
I looked at Jade and in a hoarse whisper, I told her that I wanted nothing more than to be ridiculed and degraded by the women in my life. I told her that I craved the submission demanded of me and would she please allow me the honour of being spanked by her, this morning. I looked her in the face; red cheeked and told her that I was having very naughty thoughts about her. I promised that I was very sorry, but she was so beautiful and I was so horny. She laughed and twirled around, exposing her bottom, so that I had a real eyeful.
She looked at me with real affection as she reminded me that I had no chance of enjoying any kind of sexual encounter with her or any other woman. She grabbed a handful of baby wipes and began to clean my pee covered bottom. She lifted my chastity covered cock out of the way and cleaned every inch of my bum, until she reached my puckered hole. She looked at me and told me that sissy baby girl’s bottoms belonged to their Mother’s, Auntie’s and babysitter’s. She reminded me that she was my babysitter and that I should open my legs wide and prepare for boarding. She poured baby oil onto her delicate hands and teased my bottom outrageously.
“I love the look on your face, Chrissy, when I finger your bottom! It’s precious and so very cute, just like a little girl’s face when she discovers masturbation, for the first time! With no release from your tight chastity, I suppose this is the only sexual pleasure you get, isn’t it? That’s right, my darling little girl, Jade knows how to make her baby all hot and bothered! I’ll just add another finger before I ask you a second question! There it is and here’s my question! If you had the choice of bending me over, pulling out your hard cock and fucking me or having me give you a nice big enema and dressing you in a pretty dress, which would you, choose? I should let you know, that I’ve picked out this dress for you to wear and as you can see it’s scrumptious!”
I alternated between staring at Jade’s delicious body and that frilly dress. Made of sheer white organza and covered in hundreds of delicate pink bows, it was totally sissy. I begged her not to be so cruel and to let me see the dress more closely. She lifted it in front of my face, letting the hem caress my face and lips. Jade pointed out that it was indecently short, especially after she dressed me in a matching ruffled petticoat and sissy baby bonnet. She told me that I would have to be put in a very special pair of rhumba panties under such a lovely dress and between the length of the dress and the fact of the sheer material; I’d be on total display.
She reached down and passed me the panties. Made of pale blue silk and dripping with pink ribbons, they made me whimper. Jade pointed out the 6 rows of pink ruffles on the behind and the sheer panel on the front. Stitched on the front was 1 word “SLUT!” and Jade told me that I was her nasty little diaper slut. She slapped the inside of my thighs, making my eyes water and asked me if I was her diaper slut. I nodded, but she slapped me again and told me to speak up. I told her that I was her diaper slut and could I please be allowed to wear the pretty dress. She asked me to tell her that I needed to wear this dress more than my sexual desire for her body.
In a lisping voice, I told my young babysitter that I wanted to be dressed like a diaper slut and that I preferred dressing like a sissy baby girl than wanting to make love to a girl. She laughed and promised me that I’d be going down to breakfast shortly and that she’d be delighted to dress me for the occasion. In fact she was very insistent that I understood that the kitchen was full of caterers and other strangers. I looked at her with horror as she explained that I’d begged her so well that she couldn’t bear to disappoint me. She asked me a third question.
“Do you realise that we want to destroy your male persona completely and replace it with a much more obedient little girl’s instead? Any hope that you might harbour that you could return to an ordinary existence will be ended when you marry Gemma today! She’s asked me to move in here with you and become a part time babysitter while I finish my studies at university and I intend to! When your wife is out servicing her hulking lovers, I’ll be supervising you clean her dirty lingerie and cleaning her toilet with your tongue! Imagine Auntie Gemma on all fours, taking it in all her holes, writhing in ecstasy, while you’re licking her toilet and laugh at your misfortune! You’ll be able to ask her all about her date when she returns home and I’ll love to see your face when she describes her encounters in detail! Aww, don’t cry sissy, after all you can’t expect her to do anything else, could you?”
With a sob, I begged her to please be allowed the honour of telling her that I was so ashamed of my thoughts. She nodded at me and told me to go on. I explained that I knew that my so to be wife was going to cuckold me at every opportunity and could I please have my diaper put on , as her continued frigging of my bottom was making me all squiffy. Jade told me that I was a pervert before powdering my derriere and pinning me inside 3 pairs of super soft pink cotton diapers. She fed a pair of soft pink plastic panties over my legs and tucked my diaper away. Next were those stunning rhumba panties and I was soon in-cased in my slutty knickers. Jade patted the front of my diaper covered cock and asked me if I liked my pretty panties. I told her that I loved them and she nodded before remarking that I was clearly having a ball.
Jade picked up a pair of pale blue knee high socks, made of sheer silk and topped with a large pink ribbon. Jade ran my silk socks up my calves and tied them in place with a pair of floppy bows. She then buckled a pair of black patent leather Mary Jane’s on to my feet. She stood me up and asked me if I’d like to put my petticoat on first or second. I told her first and she asked me why. I told her that being petticoated by her made me feel utterly inferior to her and without any means of retaining my manhood. She laughed and told me that I deserved to be petticoated by her and that I should get ready for my frilly underskirt.
Jade bought the petticoat in to view and had me inspect the item of clothing. She pointed out all the lace and how stiff the netting was, so that my dress would stand up and my diaper covered bottom would be displayed. She stood behind me, d****d the petticoat in front of me and whispered in my ear that I was very lucky to have such a frilly petticoat to wear. She told me that she wore petticoats like this when she was a little girl and that they made her feel totally feminine. She asked me if I felt like a girl when I wore a petticoat and nodded yes.
“Good for you, Chrissy and very well done for sharing your desire for being petticoated! Now let’s get a move on and see just how this looks on you! That’s it, step into it and I’ll pull it up and tie it around your waist! Wow, you’re a real sight, Chrissy and I bet if you weren’t locked up in chastity right now, you’d be rock hard inside your diaper! I’m right, aren’t I Sissy? Your frilly petticoat makes you feel like my diaper wearing sissy slut and I’m actually getting wet at the thought of display you at breakfast! There are at least a dozen total strangers downstairs, both men and women, who’ll be shocked when you curtsey to them shortly! Remember that you belong in diapers and if you make use of them, I’ll tell them all what you’ve done! Maybe they’ll even want to watch me change your dirty diaper or perhaps 1 of them would do the honours, sissy!”
I shuddered at her teasing talk, all the while; I longed to be publically humiliated by her and wanted nothing more than her domination. She pointed to that dress that sheer gossamer dress and asked me if I was ready. I begged her to please wear my new dress for her and have everyone see just what a pathetic sissy baby girl I was. She looked at with glee as I told her that I was so pleased that I was being a good sissy baby girl for my new babysitter. She told me that I still deserved a spanking and I should be ready to receive it downstairs before I eat breakfast and observed by everyone.
Jade lifted my dress over my head and settled it onto my body. The hem just reached the edge of my petticoat and was pushed vertically. I was buttoned inside and asked if I felt as good as I looked. I begged my babysitter to be allowed to look in the mirror but she told me to wait until the final items were on me. A pair of white fingerless lace gloves, a massive pink penis headed pacifier and my bonnet. When I was led to the mirror, Jade holding my hand in hers, I was poleaxed at my appearance. I looked ridiculous, but I felt so sexy and girly as well. I asked Jade if she thought I was girly enough for my public humiliation and she told me it needed 1 more touch.
She coated my lips in shiny pink lipstick and pushed my pacifier deep inside my mouth before tying the ribbon into a large bow around my neck. She told me that I looked perfect and led me out of my nursery, towards the noise of the kitchen and inside the full room. 7 young women were prepping and cook the wedding feast. 2 middle aged men were sorting plates and cutlery, while an older woman supervised everyone. Jade led me over to the centre of the room and in a clear loud voice introduced me to my audience.
“Excuse me for interrupting your work, but my little sissy baby girl is in need of her morning feed and in light of the fact that he’ll be marrying his bride in a few hours, she needs a full tummy! Now, Chrissy be a good girl and curtsey to the nice people and be quick about it! That’s very good, but you needn’t pretend that your ashamed of dressing like this, after all you’ve just spent the last half hour telling me that you prefer wearing diapers and frilly dresses to having sex with women! Chrissy here told me that he wanted to be petticoated, by my hand, rather than have me suck his tiny little cock! We made sure that he’d never disgrace us by getting excited, during diaper changes, by locking it away in chastity and denying her the release! Now before I feed you, there’s the matter of that spanking I promised, so come here, across my lap and prepare for a sore bottom!”
In moments, I was across her lap; my petticoat lifted away, my panties and my diapers around my ankles. Jade told me that I would receive 48 hard smacks and I should feel free to blubber and cry likes a little girl. The caterers watched with a mixture of stunned silence and curiosity on their faces. Jade spared no time in punishing me and I was soon writhing on her silk covered lap, as her hand descended. Smack after smack struck my bottom and I gave any pretence of bravery. I sobbed and cried, tears running down my face, as the caterers drew closer and closer. By the end of those 48 smacks, I was a quivering wreck and I made no attempt to help Jade re-diaper me.
1 of the young ladies asked my babysitter if I was really a man under my girly clothes and she told her that I had male equipment, but I was at heart a dirty little sissy girl. She asked the young woman if she’d like to inspect my appearance at closer range and with the others egging her on she was soon touching every inch of my clothing. When her hand reached my diaper covered bottom she asked Jade if I really used my diapers instead of a toilet. Jade laughed and told them that not only did I regularly wet myself each day, but I frequently p*o’ed my diapers, like a naughty girl.
The cook asked Jade if I’d like something to eat and she asked if they’d warm me up a bottle of formula, pointing out the cupboard where it was kept and the bottles as well. While my feed was taken care of, 1 of the men asked Jade if I was really marrying a woman later today. She smiled and explained that although I was marrying a very beautiful woman that I’d be very much under the thumb or wearing the diapers. She told them that I was nothing more than a sissy baby girl and would spend my days being humiliated. Jade caressed my legs, possessively, all the while telling these strangers that my wife would be cuckolding me at every turn.
Jade sat me up on her lap, my eyes fixed on 1 of the young women in the kitchen. She looked to be 19 or 20, dark haired and extremely pretty, but the look on her face was 1 of hunger. She seemed to be revelling in my humiliation and couldn’t take her eyes from mine. Jade noticed our silent exchange and asked the girl if she’d like to feed me lunch. She nodded, all red faced and I soon switched places, sitting on her lap and not Jade’s. The cook handed her a full baby bottle full of milk and my young temptress removed my penis headed pacifier, teased my lips with the rubber teat and pushed it inside my mouth. The young lady whispered in my ear, as she feed me.
“You look utterly pathetic! Fancy a grown man wearing diapers and little girl’s dresses, like a pervert! You’re a pervert, aren’t you? A nasty little pervert in need of very strict supervision and your young babysitter clearly has your measure, doesn’t she? Now be a good sissy and drink up all your milk. Every drop, mind you and afterwards I want you on your knees licking my shoes! I want you to show everyone here, just how disgusting you are and make them understand what I can see when I look at you! You’re a loser, Chrissy!”
My belly full of formula, I fell of the young ladies lap, at her feet and began to lick her black leather flats. I heard gasps of surprise, as I abased myself for a woman I had just met, but I knew my actions were correct. To show any woman my profound reverence due to her, is my ultimate wish. I lapped at her shoes, my diaper covered bottom in the air and on display. I felt hands caressing the tops of my thighs, checking out my frilly panties and massive diapers. I glanced behind me and saw both of the men feeling up my bottom. Jade joined them and in a crystal clear voice, told them that I was a virgin, in need of a real man to pop my cherry.
She asked them if they’d like to take part in the ceremony later, in a more direct way than planned. Jade explained that after the ceremony, Auntie Gemma would be spending some time with some of the male guests and that I would need a little company. She smiled at my discomfit, as I was pimped out to these to strange men by my young niece. They promised to think about it, but made no promises. Jade pulled me to my feet and led me back upstairs, to get me ready for the ceremony. Jade gave me a big hug and told me that she was proud of me. I looked at her in astonishment and asked her why she was proud.
“Because, Chrissy, I’m going to watch you lose your virginity later and I can’t wait to see your shame! Those men will definatly be up for it, they were just playing it cool in front of their work mates! They had massive hard on’s in there trousers and I’m sure you’ll get to see them later, you slut! Chrissy, you’re a naughty little prick tease, getting them all hard and not doing anything about it, so you’ll have to be extra nice to them! A nice blow job to start with, but that won’t satisfy them for long and you’ll need to spread your legs for them. A hard fucking of your bum will soon have you weeping, but don’t worry I’ll be right beside you, making sure that you’re a good girl and afterwards I’ll give you a big hug!”
I looked at Jade with horror on my face and she smiled at my future. I begged her not to watch my deflowerment, but she told me that I needed to be supervised during such an important event, especially as my new wife wouldn’t be there. She asked me if I’d like her mother, my step-sister, to be there as well and I begged her not to be so cruel. She giggled and told me that her mother would be hurt if didn’t want her to share in my shameful act and that I should ask her to join us when she arrived later. I nodded at her suggestion, my eyes down and my eyes tearing up. Jade asked me if I’d like a nice soapy bubble bath, while she got my dress and lingerie together.
With a resigned nod I entered my bathroom and started the hot water running. I poured in a massive amount of rose scented bubble bath and returned to my nursery to ask Jade to help me undress. She smiled and told me that it would be her genuine pleasure. In a few minutes I stood before her naked, but for my chastity device. She stood in front of me, looking me in the eyes and asked me if I’d like her to help me reach the hard to reach places. I asked her if she’d join me in a little while and help me bathe. She smiled and nodded.
I returned to the bathroom, stopped the hot water, and added some cold before entering the tub and soaking. I relaxed, for perhaps the only time today, until Jade entered and asked me if I needed a hand. I nodded and she squatted beside the tub, reached into the warm water and caressed my chastity covered cock. With total indifference to my mental state, she played with my very full balls, cupping them and fondling them expertly. She watched as my eyes rolled back in my head and I begged her to unlock my chastity, so that I could spurt. She laughed and said.
“Why would I want to do that, Chrissy? Watching you suffer, in chastity and needing release is 1 of the most fun things imaginable! Your lack of orgasm is so important to defining your submission to the women in your life and I can’t imagine a time when you’ll be allowed out of chastity! Don’t cry, Chrissy, after all isn’t it much more satisfying to mess your diapers and wear frilly dresses, instead! Sissies don’t need the release of masturbating but we’ll be sure to milk your prostate, to keep you healthy and compliant. How about I milk you now and remove all that nasty spunk from your balls! Get up on to all fours and I’ll get your milking probe!”
I crouched in my bath tub, my bottom in the air and waited for Jade’s return. I didn’t have to wait long, as she entered the room, my white plastic anal probe in her hand and a bottle of baby oil. She sat on the edge of the tub and coated the probe with baby oil. She asked me if I could have ever imagined being in this situation a few months ago, where my young niece would be getting ready to milk my prostate and empty my balls. I begged her to please begin and she laughed and told me to hush. She slowly, so very slowly, pushed that thin supple plastic probe inside my bum and searched for my prostate. I shuddered when she found it, as she expertly manipulated my body and made me squeal.
Over and over, Jade bought me to the brink of orgasm before stopping me from coming by removing the probe and having me relax. I was gasping for breath, as my cock leaked spunk, into my bath and I begged her to make me spurt. As I made this plea, Jenny, Jade’s mother entered my bathroom and asked what all this fuss was about. Jade told her mother that I was being milked before my wedding ceremony and asked if she’d like to finish me off. She grinned and said that it would be her honour. Mother and daughter sat side by side, as I was milked, for half an hour before my balls were emptied and I begged to be allowed to get out of my bath.
I was helped to my feet, my legs like jelly and propelled across the room. I was sat on my potty and told to use it, while Jade left the room for a few minutes. Jenny looked down at me as I used my potty and wee’d into it. She asked me if I was finished and I told her yes. She watched me clean my potty and told me to bring it with me into my nursery. When we entered Jade was not alone, to young women were with her and they smiled at my nakedness. Jenny explained that 1 was my hairdresser and the other was my make-up artist. I was sat at my vanity table and Jade told the 2 ladies what to do.
“Chrissy has lovely long blonde hair and you should give her a head full of curls! Lots and lots of bows pink of course, throughout her hair and made to look like strawberry shortcakes hairdo! Her make-up should be subtle, but make sure she has lots of pink lipstick and glitter on her body! She should sparkle, like a jewel and be coated in lots of perfume! Use a nice rose scented cologne and be sure to drench her cock! A perfumed chastity covered cock, but we’ll all be happy if it smells like a girl’s pussy and not a boy’s cock! Chrissy, you should tell the girls all about your fiancé and her plans for the honeymoon!”
As I sat there and was primped and preened, for the next few hours, I was expertly probed for every dirty secret of my relationship with Auntie Gemma. I spent most of my time red faced, as these young ladies laughed at my actions and activities to date. When I finally told them that Auntie Gemma would be cuckolding me tonight, they were unsurprised. In fact they told me that I was lucky to be allowed in presence of such a delightful lady and I should tell her that later. I promised to, as they left and found myself, once again, with Jenny and Jade.
They’d changed into their wedding attire and looked stunning. Jade had on a short pale blue silk dress, with a very full petticoat underneath and a plunging neckline. Her legs were covered by white silk seamed stockings and her feet were inside a pair of pale blue patent leather 6” stiletto heels. She stood next to me and I breathed in her lovely perfume. In a low voice I told her that she looked amazing and I was so lucky that she allowed me to be in her presence. She smiled and told me that I was welcome, but that she thought I was a very naughty sissy baby girl and that she just wanted to make me realise that I was in need of a very hard spanking.
Jenny was wearing a white latex pant-suit, made of shiny latex and completely figure hugging. She tottered on a pair of bright red P.V.C. ankle boots, with 5” heels and carried a thin whippy cane in her hand. She was the epitomine of dominant womanhood and I told her that I wanted nothing more than look at her. She asked me if I would like to lick her latex covered bottom and nodded, sank to my knees and licked my step-sisters bottom. Jade asked her mother if she’d like to whip my bottom before or after she spanked me. She said she didn’t care, so I was pulled to my feet and d****d over Jade’s lap for my spanking.
“It’s time for you to cry, Chrissy but don’t worry about ruining your make-up as its waterproof! A nice hard 50 smacks should teach you to know your place and I expect you’ll kick your legs, but don’t worry about feeling ashamed of being such a wimp because we both already know you’re a limp wristed sissy girl! Have you told my mother about those nice men who want to spend some time with you, after the ceremony? No, well Chrissy has attracted the attention of 2 real men and like the slut she is, they agreed to pop her cherry! Not only that, Chrissy wants both of us to be with her, while she takes cock and loses her virginity! I expect that you’ll try to back out, but you’ll be unable to, as I intend to strap you down and laugh at every moment of your humiliation!”
As I looked at Jenny, with a horrified expression on my face, Jade began my spanking and I was soon unable to do anything other than cry like a baby. When it was over, I was pulled to my feet, dragged to my changing table and bent over the edge. With no chance to recover myself, I received a hard whipping on my already throbbing bottom. 20 stinging lashes later, I was bawling like the little girl I resembled. I was lifted to my feet and helped onto my potty to recover. Jade told me to stop being such a sissy and try to be a little stronger. She knelt beside me, took my chin in her hand and looked me in the eye.
She asked me if I needed to wee or p*o and when I nodded, she told me to go right ahead and fill my potty. I emptied my bowels and bladder, as she looked on and I begged her to let me be put into diapers. She smiled and told me that I would have to be careful, as Auntie Gemma had left instructions that I should only be allowed to use my potty for the rest of the day. I went pale and told her that I didn’t think I could control myself during the ceremony. I begged her not to be so cruel, asking her what I would look like if I messed myself and made myself a laughing stock.
Jade told me that I was already an object of ridicule and if I did have an accident in front of the wedding guests, she’d be thrilled. With a giggle under her breath, she told me that seeing me utterly humiliated in that way made her wet and I needed to understand that. She pointed to her mother and said that I should check out my dress. I looked and was horrified at the frothy confection in my step-sisters arms. It was pale pink and covered in hundreds of delicate silk darker pink roses. The skirt was tiny and raised by a white lacy petticoat. I looked at my wedding dress and begged to be allowed to wear something else. Jade told me to shut my mouth and remember my place.
“You need to understand that we don’t care about what you want; only what we want! We expect you to look ridiculous in that dress and you should know that we want you to be ashamed that you look like a total pansy! You’ll be on display to dozens of people, dressed like a Barbie and you should be sure to enjoy our laughter! Not a hope of being classy, but you’ll be a complete sissy bride for Auntie Gemma and she wanted you to know that she choose this dress! She wants you to be her sissy baby bride and understand that she will be expecting you to act as her lover’s fluffer before your dalliance with the 2 real men! You’ll be able to help her have really hard cock, but be sure to suck quickly or she might get cross and spank your bottom!”
I couldn’t take in any more shocks and I begged to be left alone, but Jade laughed and told me that it was time for my lingerie. I was sent to clean out mu potty and return for her to clean my bottom. Jade laid me on my back and used baby wipes to clean me up. She told me that I was ready for my lingerie and she asked me if I liked the feel of silk stockings. I nodded yes and she produced a pair of pale pink stockings. She sat me down and rolled them up my smooth hairless legs. The reached just above my knees, so Jade used 2 pale blue silk and lace bridal garters to hold them in place, telling me that I looked very girly. Next was a pink training bra, which she stuffed with panties, dirty ones that she explained belonged to her.
Next was a pale pink silk and lace waist clincher, which was pulled tightly around my middle and made me gasp for breath. A pair of lacy silk ankle socks were rolled onto my feet before my shoes were strapped on. They were impossibly high heeled, 9” at least and forced me onto my tip toes. Jade called the ballet shoes and told me that I should be helped to walk around, as I would probably fall over without help. I was finally ready for my dress and I asked Jenny if she would do the honours. With a helping hand, I stepped into the dress and pulled inside.
Jenny fussed the dress in place, buttoned me up and tied a large bow around my waist. At the back was a long train, but the front was completely open, showing my lack of panties and my chastity covered cock. The body was fitted and tight, but I asked to look in the mirror. I gasped at my appearance and went white in horror. Jade told me that I looked divine and had me pull a pair of elbow length gloves up my trembling arms. Finally, Jenny placed a white gossamer veil over my face and I was done. I thanked my 2 grinning companions and whimpered that I was very frightened. Jenny spoke.
“You should be happy, Chrissy, it’s your wedding day and the bride needs to be a rock during the ceremony! We’ll be right behind you, as maid of honour and bridesmaid, but don’t worry about looking like a frilly pink sissy, because there’s nothing you can do about it now! So chin up and take my arm, so we can get you married! Jade grab her other arm and let’s get Chrissy out into the garden. Auntie Gemma is waiting for her sissy bride and you don’t want her to get cross, do you? So here goes, Chrissy!”
I was led through the house, into the large patio and found the 2 men who would be fucking me later, waiting there. I asked Jenny what was going on and she pointed to a large, clear plastic potty, with wheels and lots of straps. Jade giggled and reminded me that I was to be married, strapped to a potty and that I should thank the 2 real men for pushing me to my wedding. I was strapped onto my potty, a bouquet of pink roses handed to me and had my long train straightened behind me. I looked up to my step-sister and niece, asked them to please let me have a moment to catch my breath. Jenny nodded and I took a moment to compose myself.
A minute later, the wedding march rang out and I was wheeled outside. The men grinned down at me, telling me that I looked very sexy and they were looking forward to fucking me later. I begged them to leave me alone, but they told me that they intended to spit-roast my sissy body and fill me with their spunk. I heard Jade laugh at his exchange, but I soon had more pressing matters to deal with. In front of me was a large platform, decked with pink netting and pink roses. Auntie Gemma and Mommy stood up there, waiting for me to join them. Arrayed in front of them, were 30 odd people standing up and peering back at me.
There was a murmur of amusement when they took in my dress and mode of transport, but I was hurt when Mrs. Prendergast pointed at me and laughed at me. Standing next to her was a young girl, very pretty and obviously under her spell. Jade’s friends were there, as well as some others I didn’t recognise, but nearly all the guests were female, other than Miss Leanne and her large black companion Errol. 2 other muscular men sat in the front row, 1 black and 1 white and I figured that they were Auntie Gemma’s dates. I was wheeled through the guests, as I was photographed multiple times and wheeled up a ramp onto the platform.
Auntie Gemma and Mommy stood next to each other in a parody of morning dress. Made of shiny rubber and skin tight, they wore top hats and 6” stiletto heels. I approached them and was left by my 2 men. Jenny and Jade stood behind me, as I looked at Auntie Gemma with genuine terror. She bent down lifted my veil, kissed me deeply and lowered my veil again. The female minister signalled for the music to stop and launched into her monologue.
“Hello everyone and welcome to Gemma and Chrissy’s wedding! This is an unusual wedding and I hope you understand that we’ll be doing things a little differently. First we’ll be explaining all about Chrissy’s need to be owned by Gemma and just what that means before the couple exchange vows. Finally I’ll ask you all to witness the solemn moment of marriage and then we’ll be greeting the newlyweds! So let’s begin!”
The minister motioned for the guests to take their seats and we began. I was terrified and when the minister explained how I’d met, first my Mommy and then my Auntie Gemma, I lost control of my bladder and bowels, filling my clear potty. I heard laughter and whispers from behind me, as the guests spotted my accident. Jenny bent down and whispered In my ear that I was disgusting. In fact she told me that I was a very naughty sissy baby girl and she would take great pleasure in punishing me later. Jade was chuckling softly and Mommy joined her, but Auntie Gemma was shooting me daggers.
The monologue reached its conclusion, with my desire to submit, completely to my wife and have her run my life. The minister turned to Auntie Gemma and asked her to speak her vows to me. Jade lifted my veil and turned me to face her. I looked up at my stern Auntie and I whimpered under her haughty gaze. She cleared her throat and began.
“I want everyone her to know that I don’t have any feelings for this sissy, other than scorn and disbelief and that I’m only marrying her for her money. I mean just look at Chrissy, she can’t even make it through a short ceremony without filling her potty like a baby! I intend to humiliate and degrade my new wife at every turn, so if you’d like an early example of my intent, I’d like to invite you to join myself, my hunky fuck toys in front row and Errol cuckolding my sissy baby girl! Your all welcome, even Chrissy will be there, acting as my fluffer and feeling my disdain! Chrissy, you’re a total sissy and I expect you to spend the rest of your life in a state of utter humiliation!”
The crowd clapped at Auntie Gemma’s vows and I hoped mine would be as well appreciated. I asked Jenny to please turn me to face the crowd and I looked out at group of expectant faces. I started to speak but the words stuck in my throat and came out in a barely audible whisper. Jade was on hand to help, placing a mic in front of my face and giving me the opportunity. I started by explain that I was a sissy and I needed to be under the control of a determined woman who brooked no nonsense. I told everyone that I was a very lucky sissy to be owned by a stern woman like Auntie Gemma and that I wanted her to know that I deserved everything she will do to me.
A small cheer went up as the minister completed the ceremony and I was married to Auntie Gemma. She ignored me, jumping down to spend time with her fuck toys. They groped and kissed my wife without a hint of shame before taking her by hand. They headed for the house and the rest of us followed. My 2 future r****t’s spent the journey mocking me, asking me if I was looking forward to being my wife’s fluffer more than being fucked by them. I went bright red and begged them to please have pity. The laughed at me and promised to fuck me even harder.
I was the first to enter my former bedroom and take up position next to the bed. The 2 fuck toys were getting undressed and Errol joined them soon afterwards. By the time they were naked all our guests had joined us and I was harangued to get on with it. Jade pushed me forward, towards the huge men and I was face to face with 3 semi hard cocks. I looked at them without any hope of escape my humiliating fate. Errol was first and he wasted no time in fucking my face. I was at a perfect height to suck there cocks and I quickly had all 3 standing at full attention.
Auntie Gemma entered the room, wearing only hold up black stockings and stiletto heels. She came over to me and asked me if I’d enjoyed my wedding present from her. I begged her not to humiliate me so much but laughed and spit in my face. She turned round and climbed on to my former bed. She was instantly set up on by those 3 b**sts and she was filled in every hole by giant cock. I looked away in pain and Jenny bent down and asked me if I’d seen enough. I nodded and she had me wheeled into my nursery by my grinning helpers. Jade ran over to me, kissed me on the lips and told me that I was a very naughty sissy baby girl. She told me that it was about time I lost my virginity. I was unstrapped from my potty and led over to my changing table. My bottom was cleaned ready for my deflowerment.
Jenny turned me around and I was afforded the view of 2 naked men with massive throbbing cocks. Jade asked me if I liked what I saw and I begged her to have pity. She laughed and said no chance. I was helped up onto my cot and told to prepare for my fucking. I was joined on my cot by my 2 male friends, just as Jessie entered the room. She asked what was going on and Jade explained that I was about to lose my virginity. Jessie laughed out loud and asked me to put on a good show for her. I was pulled down and came face to face with a cock. I licked my lips and took it in my mouth. I felt a greasy finger enter my bottom before a much bigger invader enter.
I was being spit roasted and I was unable to take in the feelings. Jenny whispered in my ear that I looked like I was enjoying myself and I shouldn’t pretend to be anything other than a total sissy slut from now on. I was pounded hard and deep in my bottom, but I was unable to vocalise my pain because of the cock in my mouth. Jade asked me if I would like her to ask my fuckers to slow down and I nodded for her to do so but she acted like she couldn’t understand me. I was on my own. Jessie spoke.
“This is so hot, Jade! I can’t believe that your sissy uncle is getting spit roasted, on his wedding day and clearly enjoying the attention! Go on, Chrissy take that cock and drain them dry! You’ve got to remember that they’ll soon blow their loads in you and you’ll never be the same. Isn’t that right ladies? The first time a cock spurts inside you it makes you into a slut! You’ll crave cocks, Chrissy, crave the feeling of being filled up and fucked! I tell you what sissy if you can hurry up and finish them off quickly, I’ll treat you to a breast feeding! Yummy milk, for your tummy!”
I longed for the chance to breastfeed again, so I began to tighten my sphincter and thrust backwards whilst increasing my cocksucking efforts. I was soon rewarded with a massive blast of spunk down my throat and Jenny warned me not to swallow, as she wanted to see just how much I’d sucked out of that cock. I opened my mouth and the 3 ladies crowded around to check out my mouthful of spunk. They were impressed with amount and I was instructed to swallow like a good sissy.
My bum was under increasing attack and I was unable to hide behind the cock in my mouth so when Jade asked me if I was enjoy my fucking, I told her that I was in heaven. I sobbed that I needed to be used this way and hoped that in the future I would be. I begged Jessie to please allow me to breastfeed from her massive breasts and she grinned before telling me that I would have that pleasure. Seconds later my bottom was filled with spunk and my first cock was pulled out with a plop. Jenny had me reach back to my hole and feel the spunk dripping from my bum.
5 minutes later, I was alone with the 3 ladies and was grilled about how much I loved cock. I spoke hesitantly, at first, but I was drawn in to a debate about whether I’d enjoy being gangbanged, by dozens of men and filled with come. I told Jenny that I was scared, but if she thought that I could handle it, I’d be willing. Jessie called me over to her and had me sit on her lap. She was dressed in a burgundy sheath dress, made of silk and showed off her lovely figure. She lowered the top of her dress and exposed her strapless maternity bra. Made from crisp white lace, it enhanced her milk filled boobs. She opened her front fastening and they plopped out. Jessie presented her left breast to my mouth and I began to feed, hungrily.
“Good girl, Chrissy, open wide and swallow every drop of my milk like a proper sissy baby! He’s taken to the breast so easily, ladies, so maybe you could suggest to Gemma that she look for a milk maid! I’m sure a lactating lady would be willing to feed old grumpy bum here and he’d be able to fulfil a deep seated need! You need to suckle from a strong woman, don’t you Chrissy? You need to show everyone, just how pathetic you are and this does just that doesn’t it? Let’s switch over to my right breast and fill your hungry belly! I’d love for my boyfriend to see this, right now. He’d want to rip your head of Chrissy, but I’d persuade him to go easy and take payment in kind, understand? No, well he’d fuck you so hard and deep, you’d be leaking for a month!”
I finished my feeding and Jessie burped me. I asked to use my potty, but Jenny denied my request, telling me to hold on. I begged her to relent, but she laughed and told me that I wouldn’t need to empty my bowels again today. I understood I was to be given an enema and I begged her for an extra big dildo for my well stretched hole. She laughed and told me sure before asking Jessie if she’d do the honours. Jessie asked what they were talking about and Jade told me to explain. I spent the next few minutes, while my step-sister and niece set up the equipment, telling my breast feeder all about my bowel cleansing enemas. At the end of my explanation she looked shocked, but was quick to volunteer her services.
I was helped up onto my medical examination table, my legs strapped into the stirrups and my dress pulled out of the way before Jenny wheeled over the large red soapy water filled enema bag hanging from a pole. She positioned it next to me and told me that she’d added some bath salts to the mix, so that it would be extra fizzy. Next a stool was placed between my legs and Jessie was invited to sit down. She looked at me through my open legs and smiled, wickedly. Jenny passed her a massive, hollow dildo, 9’ long and 2’ wide, bright red in colour and dripping with Vaseline. I whimpered and begged for her to be gentle with my still sore bottom. Jessie slapped the inside of my thigh and told me to shush.
“Now then, Babykins, it’s time for your nice big enema and I’m going to make you feel so very sissy with my huge cock, but do you know what, sissy? You don’t have to worry about a thing, because your lovely young niece, Jenny, is going to hold your hand all the way through your well needed douche and if you feel the need to squeal and cry, you go right ahead, we won’t mind a bit! Do you know why, Chrissy? It’s because we understand completely, we understand being filled up by huge cocks and loving every moment of it! You’re a sissy slut aren’t you, Chrissy? You’re nothing more than a dirty little pervert, that craves humiliation and discipline and we’re just the ladies to provide it to you! So chin up and get ready, it’s enema time!”
With a steady and persistent pressure, Jessie worked that massive phallus into my bottom and deep inside my hole. I looked at her in horror, as she began to ease it in and out, over and over again. Jessie was fucking my bottom, as Jade looked on, a grin on her face and Jenny squeezed my hand, stroked my forehead, in a facsimile of tenderness and made me feel very strange. I begged her not to be so cruel, but Jessie laughed, pointed to my dripping chastity covered cock and remarked that if I hated it so much, why was I so wet?
I tried to explain that I couldn’t help myself, that I was so horny and begged for release from my chastity, but they giggled, telling me that I had no hope of spurting today and warning me to stop asking for such naughty things. Jessie fucked my bottom deeply and with great enthusiasm. I was putty in her well-manicured hands and when she finally pronounced my warm done, I was wide-eyed and panting with desire. Jade attached to rubber tubing to the hollow dido and prepared to open the tap. I looked at her with an open mouth, my tongue hanging out and totally incapable of talking at that moment.
She opened the valve and the first part of my enema entered my bowels. I shuddered at the shame of it all, but Jessie told me that she was very proud of me and she asked Jenny if she knew many guys who would let their girlfriends do anything like this to them. She shook her head and told me that I was incredibly lucky to have found so many likeminded ladies, who were willing to take part in my utter humiliation and that I should thank them for allowing my sissy baby girl in their presence. In a little lisping tone, I begged them to please not be so wicked, but they laughed and told me that I loved every minute of it. In fact Jenny told me that I was special, a very special little baby girl, in need of a very strict and domineering female supervision and that they would be watching me closely.
“Now then, Chrissy, let’s have no more lolly gagging and fill you up with this lovely soapy water! I’ll just squeeze the bag and force every drop into your bum! That’s it; almost there and then we can take you downstairs to the reception, for your grand entrance! Chrissy’s potty parade time! We’re gonna strap you onto your potty, wheel you into the middle of the reception and watch as you fill your potty, with this massive enema! Won’t that be fun, Chrissy? It won’t, well I think you’re fibbing, don’t you girls? See we think you’re fibbing and you’re gonna lave every minute of your special show! All the guests, your family, the caterers and your new wife will have front row seats to your degradation! I hope you understand just how much we all wish to see your face as you empty your massively filled bowels, displayed for our amusement and sob like the fairy you are!”
I burst into tears, pleading for them not to make me do this, but they were adamant, I was to be publically humiliated, once again and I had no say in the matter. The valve was shut off, the dildo removed from my bottom and I was unstrapped from my medical table. I was helped to my feet by Jenny and warned not to even think of having an accident before I was strapped to my potty and in front of the waiting guests. Sobbing, I was fussed with, my dress straightened and my hair preened before being led out of my nursery. Jessie had locked her right arm around my left and was half supporting me down the corridor towards the sounds of a party.
We entered the salon, where my potty was waiting my arrival and I once again begged to be diapered instead of this ridiculously humiliating spectacle I was about to endure. Jenny laughed, took my hand, propelled me over to my potty and sat me down with a squeal from my throat. I was having real difficulty in holding all that water inside me and was feeling desperate to empty my bowels. Jade and Jenny had me, quickly, strapped onto my potty and ready to be wheeled into the reception. I asked Jenny if she was going to wheel me inside, but she pointed across the room just as my 2 cherry poppers from earlier appeared. The joined us, all smiles and joked with Jade that they hoped I was completely filled with spunk because if not they had another load brewing in there trousers.
I cringed at the thought, but Jade explained that I was needed at my wedding reception now and I wouldn’t be free for an hour or 2. Jenny knelt down beside me, took my hand in hers and asked me if I’d enjoy a little more cock later, perhaps in front of my Mommy and Auntie Gemma, as she was sure that they’d love to watch me being a total slut. I couldn’t take my eyes off the 2 men’s crotches, they were bulging in their trousers and I was suddenly feeling incredibly turned on by the thought of being taken. I asked Jenny if I could please be allowed to spend some more time with the 2 men later and would she please ask Mommy and Auntie Gemma if they would join us.
“Not on your life, Chrissy! You’re going to ask them both, in a clear and respectful tone, if they would like to observe you getting spit roasted! In fact make sure all the guests hear your request, for our amusement and your humiliation! Chrissy, my panties are absolutely dripping and I’ll be right there with you, masturbating at your degradation! Fancy making your niece wet, Chrissy, you’re such a naughty sissy baby girl and I love you so much! I love your cute girly bottom, all wrapped up in a super soft diaper and plastic panties! I love how pretty you look in petticoats and sucking on a pacifier! I love seeing you use a potty like a 2 year old and the look on your face as you fill it with your wee! I love your utter devotion to all the women in your life and your willingness to abase yourself for our pleasure, but do you know what I love most about you, Chrissy? I love knowing that you deserve every degrading and humiliating act! You’re pathetic, Chrissy and I’m so impressed with your life choice as a sissy baby girl, after all not many men would be so utterly perverted as you! Now let’s have you delivered to your wedding reception!”
I was wheeled outside, to a large marquee that had been set up in the back garden and inside to join my new wife. All our wedding guests turned at our entrance, some of them took photos and others just pointed and laughed at my continuing potty enslavement. I was wheeled to the front of the space and spotted my wife, Auntie Gemma, sitting at a long table, drinking wine and chatting to her male friends. As I was positioned in front of her, she looked down at me and smiled. She asked me if I’d enjoyed my time with my gentlemen friends and did she need to check my bum for spunk, like a nasty slut. Red faced, I told her that Jenny and Jade had given me an enema, cleaning my hole and filling me to the brim with warm soapy water.
She stood up, walked around to me and reached down to check my heavily distended stomach. With a cackle of laughter she informed the room that I had a very special surprise for them and they should all join us. The ladies and the few young men crowded around, looking down at me with predatory glances. Auntie Gemma took my hand, squeezed it lovingly and told our guests that I needed to use my potty like a big girl. She asked them if I should be allowed to fill my potty or should I be denied the special consideration. By this time, I was sweating buckets trying to hold that massive amount of water inside me and I prayed that they would hurry up.
A discussion broke out on the merits of sissy baby girls having the option of using a potty instead of a diaper or being given the option of my potty. Sonya, the young lady we met at the lingerie store, asked Auntie Gemma if I wouldn’t be horribly embarrassed by using my potty in front of everyone and wasn’t that just what I deserved on my special day. There were murmurs of approval to this point and a consensus was reached by the wedding guests. I was told to fill my potty like a big girl and be quick about it. In seconds I let rip a loud fart and my bum expelled my enema. Jenny knelt down beside me and whispered in my ear.
“Look at all the ladies, Chrissy, they’re so very impressed with your potty filling and don’t you love pleasing them all, but look at the real men, they’re disgusted by your shameful act! I bet they would love to punish you for being so nasty, maybe spanking your bottom before having you suck all there cocks and swallowing there spunk, like a naughty slut! You’d do it, wouldn’t you Chrissy? Suck there cocks and swallow there jism, while we all watch and laugh at your disgusting display! You’d do it for me, wouldn’t you Chrissy? If I asked you to suck cock, like a whore, you’d do it and love every moment, wouldn’t you?”
Red faced, as I emptied my swollen bowels, I told my niece that I’d do anything for her, as I longed to be in her presence and wanted to express my devotion to her. I filled my potty as Jenny kissed me on the forehead before asking me if I had anything to say to my Auntie Gemma and my Mommy.
With Auntie Gemma and Mommy away on honeymoon together, I was left at home with my new live in babysitter, Jenny. I was awoken very early on the first morning, by my young niece, who checked my diaper and declared it soaking. She asked me point blank if I was capable of going a single night without having an accident and sobbed that I didn’t think I could anymore. I started to cry like a little girl and Jenny pulled me into her warm embrace, hugging me tightly, cooing and patting my head in sympathy. My face was buried in between her breasts which were covered by a silk and lace teddy. In blubbered like a baby, begging her not to tell anyone about my shameful admission and asking her to please be kind.
She lifted my head, looked me in the eyes and told me not to worry, that she would be discreet, but that she’d have to inform Auntie Gemma and Mommy. I begged her not to inform them, but she laughed, telling me that I was in no position to ask such a thing and that I should be grateful that she didn’t just tell everyone about my complete incontinence. I was horrified when she told me that I should be proud of my total lack of control, as it showed that I was a complete sissy baby girl now and that I had accepted my place in life as a diaper wetting pansy. She stroked my face and told me that I was in need of a chastisement for being such a sissy cry baby.
Jenny escorted me over to my changing table, laid me on my back and proceeded to remove my sopping diaper and plastic panties. She whistled, as she cleaned my bottom before oiling my behind and tickling my hole. I whimpered at her delicate touch, as Jenny played me like a violin, she was teasing my hole with 1 hand and tickling my balls with her other, all the while looking me in the eye and smiling at my squirming. She asked me if I’d like her to push a finger in my bum and play with hole. With a nod of my head, I begged her not to be such a tease and please would she finger fuck my sissy bottom.
“Ok, Chrissy, but I expect you to tell me all about being a nasty sissy diaper wetter and how much you love filling your diapers with wee-wee! Don’t pretend to be shy; sissy we both know just what you are and why you wet your diapers like a fairy! It’s because you can’t help it, isn’t it? You have no control over your bladder anymore and your very ashamed, aren’t you? You should be ashamed, Chrissy, ashamed because a grown man should be able to control his bladder, but we all know that you’re nothing more than a sissy baby girl and wetting yourself is your deepest desire! I love it when I see the horror on your face when I check your diaper and discover that you’ve wet yourself, but you need to understand just how much I love seeing you squirm like a pantywaist! I get wet, when you fill your diapers and you should be happy to make me so! Now let’s hear all about your wetting, Chrissy!”
With a shudder, I told Jenny that I was a nasty sissy baby girl who loved to wet my diapers and begged her to please make me fill my diapers forever. She grinned, asked what I loved about wetting my diapers the most and why. I told her that I was deeply ashamed of my lack of control and that whenever I was inspected for an accident, I hoped that I wasn’t ridiculed too much. Jenny laughed and told me that I was without a chance of such treatment. She told me that she and her Mother frequently laughed at my diaper wetting, that they thought I was pathetic and was in need of much more discipline. Jenny told me that from now on she would spank my bottom every time that I wet myself.
I looked at her in shock, as I often wet myself a dozen times a day and that I didn’t think I could handle that many punishments. Calling me a silly sissy, Jenny explained that I could ask to use my potty, instead of filling my diaper, but that she would have to supervise my wee-wee’s because I needed to understand that I was under her strict control. I nodded and begged her to allow me the use of my potty for wee-wee’s, but what about when we were away from home or with company. Jenny smiled and told me that I shouldn’t fret, that I should feel free to use my potty anywhere, as she knew I was only happy when being humiliated, publically. She told me that she’d love to see me sat on my potty, holding my dress and petticoats up, knickers around my ankles, weeing in the middle of a busy shop.
I went bright red at the thought and Jenny told me that I’d be exposed to dozens of people, as a pathetic sissy baby girl and that I should be happy at the thought. I begged her not to be so cruel, but she shushed me and told me that I should open my legs as wide as possible. Jenny slowly pushed her middle finger into my bum, tickling my back passage. I whimpered at her delightful touch and told her that I’d do anything she wanted, that I needed to be humiliated by her as I was very much attracted to her. Jenny laughed, told me that she understood my desire, but that she thought that I was beneath her and the only kind of attention she would give me was as a very strict babysitter.
“Do you fantasize about me, Chrissy? Do you imagine serving me intimately, as my body slave, perhaps bathing me or helping me dress! You’d like to dress me in my lingerie, wouldn’t you? I’d be naked in front of you, sissy, not a stitch on, but I would be in complete control of you, wouldn’t I? Imagine rolling stockings up my long legs, attaching a garter belt before putting my panties over them and covering my, wet, naked sex! I’d be dripping, knowing just how close you’d be to my pussy, but you’d be denied any hope of touching me down there, Chrissy and do you know why? It’s because you’re a tiny dick loser, who belongs in diapers and frilly petticoats instead of getting into my knickers! Would you like to be my body slave or would you prefer to be my dirty little sissy girl, instead?”
As Jenny pushed a second finger in my bottom and I tried, desperately, to be in control of my squirming body, I told her that I would be honoured to be her body slave, but I was under no illusion that I was destined to be her diapered sissy slut. I begged her to please tickle my swollen balls, while she fingered my bum and make me milk. Jenny told me not to be so presumptuous, as I wouldn’t be milking any time soon, as Auntie Gemma had left instructions for me to be teased relentlessly, but be denied even a milking till she returned and decided if I deserved to milk. Jenny explained that I was expected to forgo any release, until Auntie Gemma became pregnant by 1 of her black lovers and I was beside her in the delivery room, my cuckoldry displayed to the doctors and nurses, when a black c***d emerged.
I would be expected to explain that I was nothing more than Auntie Gemma’s sissy baby girl and that I had begged her to cuckold me as I had a tiny cock. I whimpered, as Jenny laughed and told me that I’d be ridiculed by everyone there. Jenny finished playing with my bum, removing her fingers with a plop and went to wash her hands. She returned shortly and I expected her to begin my morning enema, but she told me that they’d be a change to my usual routine. Jenny led me into my bathroom, to a waiting bubble bath, her hand in mine and gently goosing my bottom.
She helped me into my bath and proceeded to help me bathe. Jenny was bubbly, making small talk about my favourite dress and frilliest petticoat.
My wife, Auntie Gemma’s honeymoon had begun. She’d jetted off to Bali with her 2 muscular black friends and left me in the capable hands of my young babysitter, Jenny, for the next 2 weeks. I knew that she’d left instructions for Jenny, guidelines for my care and treatment, but I was not privy to them. I awoke on that morning, early, after seeing Auntie Gemma off, with a soaking wet diaper and a grinning young niece waiting. I was so embarrassed as she cooed down at me and whispered that she understood my diaper wetting, after all I was a dirty little sissy baby girl and she was here to take care of my perverted needs.
She helped me out of my cot and over to my waiting changing table. Jenny pulled off my onesie, lowered my plastic panties and removed my full diaper. I lay in front of her, my crotch and chastity covered cock on display, as she wiped me clean before putting me in 3 pairs of massive pink diapers. Jenny used 2 sets of Peppa Pig diaper pins to secure my portable toilet before pulling a pair of white see through plastic panties over them and tucking me inside. Next was a pair of pink frilly rhumba panties, dripping with lacy bows and ruffles. She grinned at me and told me I was ready for my day.
“Hello Chrissy and can I tell you just how cute you look already! I’ve got a big day planned for you and you should prepare yourself for a very humiliating first day! We’re going to spend the day with my mother, your step-sister Jade and her friends! Don’t look so scared, she’s told them all about you and they’re looking forward to meeting you in the flesh! Don’t cry Chrissy, I’m sure it will be alright and if it isn’t, well you have nobody to blame, but yourself! Now suck on your pacifier. Like a good girl and I’ll take you down for your morning feed! I know Chrissy, your ever so hungry and thirsty, but don’t fret; I’ll soon have you fed for your outing!”
Jenny helped me down from my changing table, holding my hand and singing a very c***dish lullaby; all about how sissy baby girl’s needed there bottoms spanked every morning. She seemed to make up every phrase and verse, with the sole expectation of humiliating me further. She sang about my wedding night shenanigans, how I’d taken cock and clearly loved it. She sang about my wife, Auntie Gemma going on our honeymoon, with her 2 young lovers and just what they’d be up to. She finished off the ditty, as we entered the kitchen and she helped me up into my adult sized high-chair. I was strapped in, very securely, as Jenny collected my breakfast. Laid out, in front of me, on my chair’s fold down table, were 2 very full baby bottles of milk and a large bowl of mashed up vegetables.
Jenny bent down, displaying her ample cleavage and giving me a long look at her young breasts. Jenny was wearing a pink cotton and lace top, with matching panties and a pair of 3” frilly stiletto heels. She pulled my chin up and in a clear, brooking no nonsense tone, asked me if I was staring at the breasts of my own niece. Red faced and sweating, I admitted the truth, that I found her deeply erotic and that I wished that I could be allowed the honour of worshipping her in the most intimate way. Jenny shook her head and asked me if I would be willing to act as her toilet paper, until my Auntie Gemma returned. Trembling, I asked her if she meant that I was to be allowed to lick clean her divine holes.
Jenny looked at me with wide eyes and told me that I would have that honour. I whimpered and she asked me what I was surprised at. I told her that I loved her, not like an uncle loving a younger niece, but as a sissy baby with no hope of reciprocation. Jenny laughed and told me the truth that I was nothing more than an interesting diversion. She licked my ear before lowering her mouth onto mine and kissing me deeply, our tongues enter twining, her mouth like a suction device and her breathing rushed. She pulled away, suddenly, looked me in the eye and told me that I was very sexy.
“You are Chrissy, don’t be coy, sissy, we both know that you’d do anything for me and be grateful for the opportunity to serve! I’ve decided from now on that you won’t have an enema, for the foreseeable future and you should be prepared for some very messy diapers! There’s no need to cry, sissy, you’ve got no say in the matter and you should be thankful! I’ll be on hand to change your p*o filled diapers, whenever you’re in need! I’ll be ever so gentle, Chrissy and I’ll be sure to show everyone, just how little control you have! My mother will take great delight in seeing you squirm for her pleasure and when her closest friends point at your humiliation, laughing at your pathetic chastity covered cock, I’ll give you a massive smile, knowing that you hate every moment! You’ll be nothing more than a diaper filling sissy baby girl and we’ll all know it!”
I begged her not to be so cruel, but she laughed, telling me not to be so sensitive. Jenny began my feeding with a large bowl of cold, mashed swede and several full bottles of formula. I was covered in a large pink plastic bib, come apron, with a trough at the hem and a large blue teddy on the front. Made of white and blue soft plastic, I was fed like a 2 year old, most of it down my front, collecting in my bib and then forced in my mouth. I swallowed that foul swede, but at the end I was angry at her treatment of me. I asked her if I could please have something more edible in the future. Jenny sneered and told me that I should be grateful for what I received. I begged her forgiveness, but she grinned that I would have to be spanked for my presumption and that I should prepare for punishment.
Jenny helped me out of my chair, wiped my face clean with a baby wipe before leading me over to a high backed chair and pulling me across her scantily clad lap. My bottom was at her mercy and she revelled in my submission, as she tickled the backs of my thighs and inside my diapers. She asked me if I liked the idea of being displayed for her mother’s friends and whether I’d like to be totally humiliated by her. I asked what she meant and Jenny whispered that she would be very happy to explain where my new wife was. I looked at her with tear filled eyes and begged her not to be so cruel, but she laughed and told me that I deserved nothing less.
Jenny smacked the back of my smooth thigh, just below the edge of my plastic covered diapers and asked me if I would be willing to take 50 more. I begged her not to spank me, but she stroked my diapered bottom and promised me a special treat if I took them all. Teary eyed and quivering, I looked back and promised her that I’d be a good sissy girl. Jenny clapped her hands before laying into my behind, with gusto and making me wail like a little girl. I took another beating, on my constantly tender upper thighs, like a pro and did my best not to squirm like a complete loser. At the end of the punishment, Jenny pushed me to the floor and told me to follow her and my hands and knees, leading me towards the guest bedrooms.
Jenny beckoned me inside, pointed to the floor at the foot of her bed and told me to kneel. She went over to a wardrobe and pulled out several garment bags. Removing 3 different dresses, each quite formal and sophisticated, she asked me to help her choose which 1 to wear for our visit to her mother’s home, later. Each 1 was beautiful, but for me there was only 1. Made of sheer chiffon, light pink in colour and with a pencil tight skirt, it oozed sex appeal. I told Jenny that she would look spectacular and promised to be in awe of her. She looked at me with derision, telling me that I was pathetic, but that she would allow me this indulgence 1 time and 1 time only.
“Now then Chrissy, I’ll need you to pick out my lingerie as well and remember that this event is semi-formal, so no slutty or provocative choice’s! Let’s start with stockings, shall we? Sheer white silk, with a seam and a nice lacy garter belt as well, perhaps this 1, Chrissy? Ok then, next is a bra, it should be delicate and supporting, without looking to frumpy! This 1, no, maybe this 1, yes this it, isn’t it delightful, Chrissy? It’ll look lovely with these panties! Ok, just need shoes now and I know the perfect pair, very high and shiny! Don’t sit there gawping, Chrissy, help me get dressed!”
Jenny quickly pulled her top over her head, dumping it on the floor and pulling down her panties, till she stood in front of me, naked. I stared at her in a state of unbridled lust, my 19 year old niece and I whispered that I thought she was stunning. She began posing, in a series of display’, obviously seeking to turn me on and succeeding. She looked at me with hooded eyes and licked her lips. She pointed to her panties, white silk French knickers and told me to pick them up. Gently I obeyed, lifting them with reverence before being asked to sniff them and tell me if I thought them fragrant enough. I told her that I could smell detergent and fabric softener, so she had me pass her a bottle of French perfume before dowsing them in scent.
Jenny had me hold them out in front of me, as she stepped in to them before settling them in place. My niece bent over and asked me if her bum looked good in these knickers. With a full throated reply, I told her that they were perfect and asked her if I could, please, have permission to roll on her stockings. She laughed at my begging, but nodded all the same and I opened the packet, removing the silk stockings. Trembling, I rolled first 1 and then the other, up Jenny’s smooth legs before asking her permission to use her garter belt. Made of white lace, silk and ribbons, I clipped it shut before turning it then right way around. I clipped the 4 garter tabs to the stockings and then spent the next 5 minutes straightening the seams.
When I was finished, Jenny had me stand to help her on with her bra. To my mind, a bra is the ultimate symbol of femininity and this example lived up to the hype. Made of white silk and lace, it clipped shut at the front and was strapless. Trembling, I closed the bra and turned it around. Jenny settled it in place, cupping her full breasts, making me drool at her display and asking me if I liked what I saw. Jenny stood in front, in just her lingerie, her hands on her lips and a wicked smile on her perfect face. With a nod of her head and a swift hiss, I was directed towards a pair of pale cream stiletto high heels, 6” high and very shiny. I placed them on her silk covered feet and looked up at her in worship of her beauty.
“That’s a good spot for you, Chrissy, gazing up at me, dressed in my sexy lingerie and knowing that you have no hope of any sexual release! You must be incredibly excited right now, but you’ve no chance of getting kind of satisfaction and I think you love it, don’t you sissy? You love being so close and knowing that you have no hope of enjoying a normal relationship with a member of the opposite sex! Your cock locked away in chastity, buried deep inside a lovely soft diaper and a pair of crinkly plastic panties! It’s better than having a hard on, isn’t it, Chrissy? Better than a stiffy in your boxers, when you see a pretty girl and get turned on, but know she’s out of your league! You understand that all women are out of your league now and find you utterly repulsive!”
I cried at her cruel jibes, but I knew she was only telling the truth. I was pathetic, I did prefer the feel of diapers and plastic panties, to the hope of being with a women. I told Jenny that she was right and I loved my super soft diapers. Jenny lifted my eyes to hers, looked at me with real compassion and told me that she agreed. In fact Auntie Gemma had left my chastity key with her mother and I was honour bound to enquire about it later, when I’d been inspected by her and her friends. Jenny pointed to her dress and I stood, helped her in to it and zipped it closed.
My niece stood in front of me, dressed in a very sexy, pink chiffon dress, the hem above her knee and her lingerie on display, through the sheer fabric. Jenny sat at her vanity table, quickly applied make up and sprayed on perfume, in particular her panties. Finishing off her outfit were a pair of elbow length white silk gloves and a pale pink wide billed hat, which was perched on her blonde hair, at an angle, completing a look of dangerous sexuality. I was so very turned on right now and I was treated like scum. Jenny took my sweaty hand in hers, pulled me to my feet and led me in to her bathroom. She knelt me on the floor, in front of her toilet and asked me to inspect it very carefully.
I looked at the porcelain bowl, inside the pan and out before lifting the seat with my mouth. Jenny looked on with a sense of real intent, her eyes gleaming and asked me if I could lick the inside of the bowl. I looked back at her with horror, but one look was enough to understand her determination and acquiesced to her demands. I slowly licked the inside of the white porcelain bowl, running my tongue over the cool hard surface and shuddered at the shame of it all. Jenny squatted down beside me to get a closer look and she smiled a grin of satisfaction.
“Good girl, you’re doing wonderfully and I’m so very proud of my sissy baby girl! Fancy licking a toilet, like an utter degenerate and having your young niece watch! You’ve got no understanding just how pathetic you look, do you? Dressed in diapers and plastic panties, frilly rhumba panties and humiliating you for my enjoyment, as well! It’s true, Chrissy, I do enjoy watching you humiliate yourself, but I want you to lick harder now, harder and deeper. That’s it, get your head inside the bowl and lick every inch like the submissive slut you are! I wonder if Mommy would be interested in seeing you perform this task for her later, hmm. I’ll remember to ask her when we arrive at her home. Now be a dear and lap up a little of the water, like a cat would and swallow it down for me! Don’t wait; show me just how much you desire to be controlled by me, by drinking my toilet water!”
I obeyed. I was so under her thumb by now and very much in love with her that I’d do just about anything for her. I lapped up some of that water and she giggled, clapped her gloved hands in glee and told me that I was her favourite sissy baby girl. She stood me up, looked me straight in the eye and told me that I was a very dirty young lady. Jenny told me that dirty girls like me deserved to be punished for such nasty activates and she intended to make me pay. I asked her what she was going to do, but she smiled and told me to wait and see. She took my smooth hand in hers, led me out of her bathroom and bedroom, down the hall and into my nursery.
Jenny explained that I would need a jolly good scrubbing and that she would be giving me a nice big bubble bath now. She headed into my bathroom and I heard her start my bath running. She returned after a few moments and asked me to help her remove her gloves before picking out a heavy red rubber apron. She tied around her perfect waist, looked me over and whispered that I was in need of a deep probing by her. She pulled on a pair of matching rubber gloves, took my hand and lifted me onto my changing table. In moments I was rendered naked, except for my chastity device and she bent down before blowing a big raspberry on my lily white stomach.
I giggled at her totally unexpected act, it tickled and I couldn’t help myself, but Jenny took it as an open invitation to repeat the act. Over and over again, I was tortured by an act of dominant motherhood. I was unable to control myself and I let out a sigh before weeing, all over my changing table. In a moment my niece went from laughing and playing, to a much stricter caregiver. She slapped the inside of my thighs, very hard, half a dozen times, until the tender flesh glowed red. She called me a very naughty girl and promised me that she would brook no nonsense from me.
She grabbed a handful of diapers before mopping up the mess and lifting me down to the ground. She had me hold the pee soaked diapers, follow her into the bathroom and deposit them into my dirty diaper pail. I was ordered to hold open the urine soaked diaper pail and look at every one of my accidents. She stood next to me and gently asked me what they were. I whimpered that they were my dirty diapers, but she wanted more from me I could tell, so I added that I was unable to control myself and I needed my diapers to stop my shameful secret need.
“That’s right, Chrissy, you need your diapers, don’t you? You need a very strict and demanding lady to pin you inside a soft, full diaper, to allow you the hiding place for your wetting, don’t you? You’re to be imprisoned in your shameful cocoon because you’re unable to be a real man and I want you to know that I love seeing you mess yourself, in front of me! The look in your eyes when you lose control makes me wet, Chrissy and I’m almost unable to stop myself from masturbating every time you fill your diaper, but do you know what stops me, sissy? It’s because I’m not a weak willed pansy like you and I’m able to exert control over my base desires, but you can’t help it, can you? Now be a doll and tell me you love me!”
In a barely audible whisper, I told Jenny that I loved her, but asked her not to be so cruel and please stop teasing me so much. She reached down cupped my swollen balls in her rubber covered right hand and squeezed. She told me that chastity wearing sissy baby girls deserved to be teased relentlessly and she would continue to make me cringe at every chance. She kissed me gently on the forehead and told me that I was a pantywaist, her frilly little sissy and I was nothing more that hers for the next 2 weeks. She pulled me up, led me over to the massively filled bath, a huge flowerily scent emanating from the bubbles and helped me in. She sat me down and began bathing me like a c***d.
I am a c***d I suppose, albeit a grown man on the outside, but deep down inside, I’m a 2 year old girl incapable of looking after myself and shuddered at the thought. Jenny gently washed every inch of my body before having me get on all fours, arch my back and stick out my bum. She asked me if I was ready for a nice clean bottom inspection by my babysitter and did I want to know why she was doing this. I shook my head and asked her why. Jenny giggled and explained that she wanted to. That she wanted to push her fingers inside my bottom, to finger my bum, because it amused her and that I jolly well better be thankful for such attention. In fact she asked me clearly if I wanted 3 or 4 fingers up my bum before tutting and telling me that she’d just have to see how many I could take.
Pouring lashings of baby bubble bath liquid onto her rubber covered hand; she coated each finger and squelched them, behind my head. She then placed her free hand at the base of my back, forcing it down and making my bottom even more accessible. With no warning, I felt her ease her lubricated middle finger inside me and I whimpered in shame. Jenny asked me if I’d like to know who would be joining us at her Mothers for morning tea and I nodded. With a light tone she told me that 2 of her Mothers oldest friends, along with their teenage daughters, would be allowed to see just what a pathetic diaper wearing sissy I was and that they’d be sure to laugh at my shameful appearance. Jenny eased her index finger inside me and commenced a slow, languid fingering of my bottom, all the while describing what would be happening later.
“Mothers dearest friend is a stern and strict woman called Catherine. She’s so looking forward to meeting you and introducing you to her 15 year old daughter, Allison! You’ll be glad to know that you’ll also have the honour of being presented to Lauren and her 14 year old daughter, Alexis as well, but don’t worry about being a disappointment, Chrissy, as you’ll be the star attraction the first time you mess your diaper in front of all us ladies! You’ll be unable to hide your shameful dirty diaper for long and I’ll make sure that, Allison and Alexis are the first to change your bottom, sissy! Fancy having your dirty diapers changed by a pair of young ladies, while we watch and laugh, because they’ll be sure to tell you just what they think of you and your nasty little chastity covered cock! I bet they won’t be able to stop laughing, as they clean your bum and pin you inside a clean diaper before pulling up your plastic panties and making rude comments about your tiny cock, Chrissy! A pair of teenagers, barely out of their own diapers, will be amused at your predicament and they’ll be right, won’t they? You’re a tiny cocked diaper wearing sissy baby girl and they should make you feel humiliated!”
I begged her not to be so utterly stern with me, but Jenny laughed and told me to be quiet before forcing her third finger inside my bum. I was panting from her slow, rhythmic teasing of my hole and she made sure to draw out every moment. I was asked if I’d like to wear a very pretty dress for morning tea, but before I could answer, Jenny told me that of course I would and she would find me a lovely petticoat to wear as well. She whispered in my ear that it would be very full and frilly, so that my diapers would be on display for everyone to see. She licked my ear and told me that some nice shiny tights would be a very nice touch, as well, because I had lovely girly legs and I’d want Allison and Alexis to see my shapely thighs, as well.
With another nibble of my ear and a kiss to the back of my neck, Jenny added a fourth finger to my frottage and I melted inside. I begged her not to stop, as it was divine, but she asked me what I’d be willing to do for her and I looked at her with hooded eyes and promised her that I’d do anything. Jenny slowly eased her fingers out, making me gasp before asking me if I’d be willing to wear an extremely humiliating baby bonnet, one that was without parallel and would be so over the top that I’d be mortified to be seen wearing it. I begged her to put me in whatever frilly, humiliating outfit she wanted to, but to please not stop frigging my bum. Jenny stopped and told me that I should beg her to be dressed like an utter sissy baby girl, for her amusement and my humiliation. In a loud clear voice I begged her to dress me in the most degrading and debasing way she could imagine, but I could take much more of her drawing out her teasing. She laughed and slowly eased her fingers back inside me.
“Just so you understand, sweetie, I get to go completely over the top today and you’ll be begging me to dress you this way! You’ll be made to look utterly ridiculous by me and the only words out of your mouth will be pleading for even more frills! I want you to be under no illusion, Chrissy, that when you’re shown off to my Mothers friends, that they’ll be in stiches at your total lack of masculinity and your overwhelming femininity! Not our kind though, strict, sensual and beyond your ability to reach, but a little girls dreams of being a fairy princesses! A silly little sissy baby girl who deserves there scorns and ridicule! I’ll ask them if they’d like to know who picked out your outfit and I want you to explain that you did, because you wanted them to see just how much you love being a diaper wetting baby girl and could they please watch as you lift up your dress before showing them your frilly rhumba knickers!”
I promised, in the most pleading tone possible, as she made me into her glove, by adding her thumb to her other digits and fisting my bottom. Jenny told me that I should get ready to milk now as she’d got everything that she needed and I would be much more docile for the pretty young ladies if I didn’t have quite so much pent up spunk in my throbbing balls. With no pause, Jenny manipulated my prostate and I leaked my spunk, through my chastity and into my bath. I had no sense of release, as I was milked expertly, until I was drained dry before being sat up, white as a sheet and given a shampoo by my babysitter.
Jenny made sure to scoop up as much of my jism as possible and use it as well as baby shampoo. She whistled a little tune under her breath before singing a cheerful song about a sissy having a lovely spunky clean head and no more throbbing balls. I was lifted from my bath, soaking wet and sparkling clean before being dried off with a big fluffy cotton towel. I was red skinned and in no state to protest as I was led out, into my nursery and sat at my vanity table. I looked at my red face in the mirror and barely recognised myself from before this all began. Although I was oversized and clearly male, the subtle changes made to my appearance made me seem quite juvenile. Not 1 hair was visible anywhere on my body, other than my head and they were long, perfect for pigtails or bunches.
My body was completely devoid of muscle or bulk, my diet of milk and mashed vegetables, coupled with a complete lack of physical exertion, had made me into a weak baby. Jenny asked me if I had anything I wanted to say to her and in a clear, scared voice, I begged her to dress me in the most humiliating sissy outfit she could find. I looked her in the eye and told her that I needed to show Jade’s friends, just what a frilly sissy I am and make their young daughters tease me for being in there presence. Jenny smiled and told me that she’d be proud to oblige before taking my hand, leading me over to my changing table and laying me down. Jenny reached for some diapers and pins.
“I don’t think 3 sets of diapers are quite enough for today, do you Chrissy? No, well we’re in agreement then, aren’t we! 4 pairs and some absorbent diaper pads as well, to soak up your mess and keep it all inside! Let’s start with some lovely baby oil on your bottom and then lots of baby powder to prevent baby’s bottom getting to sore! Now lift up your bum and I’ll pin you in your diapers, Chrissy! I’m using 3 sets of pins, with this darling ducky motif, because they’ll never hold with less! That’s perfect for a sissy like you, sweetie, massive diapers and a more impressive pair of plastic panties! These are so you aren’t they? Butter soft and translucent so we’ll be able to see what’s happening inside, so let’s be having you, lift up your bum and I’ll pantie your well deserving bottom!”
In moments, I was wearing those massive plastic panties, edged with frills and elastic to form a waterproof seal. Jenny tucked in my diaper and I was once again safely encased in my portable toilet. I was asked if I knew what was next and in a quiet voice said that I would love some shiny tights for my girly legs. My babysitter smiled at me and told me that it would be her pleasure. She went over to my selection of hosiery, picked out a packet and bought them over to me. Jenny removed them carefully and showed me my tights. Sheer white, with pink pacifiers running down the legs, they shimmered with glitter and were totally in keeping with my sissy desires. Jenny knelt in front of me, rolled the tights up my legs and had me stand so that she could pull them over my massive diapered bottom.
Once they were in place I was asked if I’d like some rhumba knickers, now and what kind did I want to wear. I begged her for a pair of utterly girly knickers, so that everyone would know that I loved be a sissy and please could they have a naughty message on the front. Jenny rummaged through my knickers drawer and bought over 2 different pairs. The first were barely there, sheer with rows of pink ruffles stitched to the white silk bottom. The phrase “COCKSUCKER!!” emblazoned on the front. The second were a pair of pale blue silk knickers, edged in pink lace and dripping with pink lace bows. The phrase “DIAPER-FILLER!!” on the front, in large letters. I looked at them in horror, but I knew what I was expected to do, so I pointed to the second pair and begged for my frilly rhumba knickers.
Jenny knelt in front of me, held my knickers open and I stepped into them. She slowly drew the up my nylon covered legs, over my diapered behind and fussed them into place. She possessively rubbed my bottom and asked if I’d ever dreamed that I’d be so lucky to be wearing such gorgeous knickers. I sobbed that they were perfect, but that I needed some footwear to protect my nylon covered feet. Jenny nodded, produced a pair of pink cotton ankle socks, edged with lace and a pair of black patent leather Mary Jane’s. In moments I was wearing both items and standing beside her, looking in the floor length mirror, as she rubbed the backs of my thighs. I begged Jenny for a petticoat next, but added that I deserved a very full and lacy 1 so that my massive diapered bottom would be on full display. Jenny picked out a very frilly petticoat and bought it over for me to see.
“I think this is just what you asked for, isn’t it Chrissy? Look how much lace and went into the layers of organza! It’s very stiff as well and should be able to lift up any dress, so that everyone can see your diapers, isn’t that what you said? That you wanted to display your shamefully diapered bottom to us all and make sure we all now just when you mess your diaper! Don’t pretend that you don’t want us to know all about your messing, Chrissy and I won’t tell the girl’s about how much you love the fact that your wife is cuckolding you, on your honeymoon and with your full knowledge and consent! Maybe you should tell Allison and Alexis all about the cock that Auntie Gemma’s swallowing why you fill your diapers for us instead! Maybe I’ll tell them that you prefer pooing in your diapers to making spurties! It’s true, isn’t it Chrissy! You prefer messing your diaper to spunking!”
Red faced and with a hanging head, I nodded as she laughed at my latest confession. She told me that she wasn’t surprised, as she suspected that I needed the feeling of utter humiliation to replace my physical orgasm with a symbolic one instead. From now on, she would allow me multiple diaper messes every day and when I had a full diaper, I was to tell her that I’d made spurties in my diaper for her. If we weren’t alone I would be required to explain that I had ejaculated a load of p*o-p*o in my diaper, like a big sissy baby girl because I loved to do it more than spunking like a real man and that I was much happier doing my business this way.
I went white as Jenny gave me my instructions and I tried to regain some semblance of control by asking her if I could please be allowed to wear my frilly petticoat today. She grinned and sure, but I’d better be sure, as she thought that I’d be completely exposed and I’d never get the respect of her Mothers friends. I nodded and with a smile on her face, she had me step into my petticoat before tying it around my waist and fluffing it out. Next I was asked if I’d like a nice lacy vest to wear and I nodded and begged her to pick out a girly vest for me. Made of pale blue silk and edged in pink lace, it matched my rhumba knickers, perfectly. Next was my dress and I proceeded to get on my knees, my petticoat splayed around me and begged Jenny for a dress worthy of a sissy’s total emasculation, in front of too strange women and their teenage daughters.
We spent the next several minutes, perusing my hundreds of sissy dressed before Jenny settled on the choice. When she pulled it out I almost fainted. It was utterly without shame. A dress with only 1 use, my total humiliation and looked at Jenny’s smiling face, as she asked me if I had anything to say. I begged her to please allow me to wear that dress to today’s morning tea, as it would make me look so sissy for everyone to see and I’d be so happy to be the centre of attention. Jenny nodded and had me bend so that she could dress me. Made of sheer pink glass silk, with a Peter Pan collar and huge puffy sleeves, it was very short. High waisted, once my petticoat held up the lacy hem, I’d have no hope of being hidden from view and I was right, in moments I was wearing that dress and my heart almost stopped.
“Well take a look at Miss Sissy! That’s so right for you; it screams pantywaist, as well as slut and allows us to inspect your diaper at will! The ladies will be open-mouthed at your darling choice and make sure you tell them you begged me to wear this dress! I want you to be completely forthright with our newest members of your fan club! You’re going to be so ashamed by the time I get you home that you’ll be begging me to never take you out again. Before we leave Mothers today, she wants to spank your sissy bottom, in front of her friends and I’m letting her do it, Chrissy! Now don’t pretend that you don’t need a very public punishment, legs kicking and crying like a little girl, I’m sure you’ll make a very interesting end to this morning’s gathering! Now let’s finish off your outfit!”
Jenny led me over to my vanity table and proceeded to style my hair. She gave me long floppy bunches, tied with 2 large white ribbons and finished into bows. Next she made me up. A light foundation, followed by light pink lipstick and shiny lip gloss, a light blush and some freckles added with a make-up brush. Finally a little eye shadow and eye lash brush. Jenny then sprayed me with a large amount of sweet smelling perfume. She stood me up and gushed, telling me that I looked good enough to eat. She swept me back over to clothing area and told me that I needed a nice hat.
I remembered her instruction from earlier about a frilly baby bonnet and begged her for the most outlandish 1 in my collection. I already knew which 1 she’d pick; it was massive, made of white lace and befrilled with pink silk roses. She placed it on my head, attached it beneath my chin with a large strap and cooed at my submissive demeanour. It was impossible to be anything more than submissive dressed as I was, so when Jenny pulled a pair of white lace fingerless gloves onto my hands, I simply sat there and took it. I was pulled to my feet before I had a large pale blue silk and lace apron tied around my waist. I was led by the hand, over to my floor length mirror and took in the complete outfit for the first time.
It started with the dress and how short it was. The petticoat aggravated the effect, showing my diaper covered bottom, huge and covered in those knickers. The phrase “DIAPER-FILLER!!” very prominent, but I spotted a new aspect on my recently added apron. Stitched in pale pink was a large erect penis, dripping come, onto a large pacifier and with the phrase “TASTY!” above the image? My legs were shaking in my tights, as Jenny ran her hand over my diapered bottom and asked me if I had anything to say to her. In a shaking voice, I told her that I looked utterly sissy and I begged her please not take me out today. She smiled and told me what I should do now.
“You can forget about staying at home, because we’re going to a very special tea morning and you’re the star attraction! You’ll be so very sorry that you told me that you love me, because I intend to use it against you and you’ll be powerless to resist! Now let’s head out we’re due to arrive in half an hour and I hate being late! I’ll just grab a diaper bag full of supplies and we’ll be ready to head out! Now let’s fill up your mouth with a nice big pacifier and I have just the perfect 1, here take a look, it’s pink and has a nice 3” penis shaped teat! Open wide sweetie and you can suck on your diddum’s!”
Jenny pushed it into my mouth and tied it tightly around my neck. I had my baby reins attached and was led through the house, out front and to my special baby van. I was strapped in the back, in my push chair and told to be a good girl. Jenny got into the front and started the engine. I was afforded the sight of a shot up Jenny’s skirt to her stocking tops and her pantie covered mound, on the specially positioned camera. She spoke through the intercom and asked if I’d like a movie to watch on the journey. Without paying a moment’s notice to my pleas, she put a hardcore sissy maid video. In it a young sissy maid was degraded, beaten and humiliated by a strict dominant woman before she watched as he was fucked by a massive cocked black man at the end.
I had become absorbed in the movie and didn’t realise that we’d arrived at our destination, until the final scene ended. The young sissy maid was licking the stiletto heels of his mistress in submission, as she stroked his hair tenderly. The final sentence made me shudder in desire. The sissy maid looked up at his mistress and thanked her for his well-deserved punishment before calling her Mommy. I was startled when the door was opened and Jenny un-strapped me from my pushchair. She took my baby reins in 1 hand and my diaper bag in her other before leading me down the drive to a large door. She rang the bell and told me to stop fidgeting; after all it was only my step-sister coming.
Jade opened the door, looking radient in a lovely red silk pant-suit, with a cream silk blouse and 6” black stiletto heels on her feet. She towered above me, but stood back to take in the full effect of my outfit. She smiled at me with a glint in her eye and asked Jenny if she’d had any bother dressing me in such utterly humiliating outfit. Her daughter laughed and told her that I’d begged for each item, because I wanted to show her Mother just what a pathetic loser I am. I was pulled inside, through a hallway and into a large living room. Several large leather couches, single chairs and surrounded a red rug. I was led over to the rug, sat down and given a large bottle of milk, as my reins were removed by Jenny. Jade stood over me and explained that her friends would be here soon.
“You’re going to love my friends, Catherine and Lauren! They’re very much your cup of tea, strict, domineering and beautiful, but willing to take pantywaist’s like you in their strides! Allison and Alexis, their teenage daughters are so looking forward to meeting you! You’ll be their first sissy, so you better not disappoint or they’ll be hell to pay, my girl! Be obedient to my guests, no matter how humiliating or degrading their orders and I’ll be sure to give you a nice treat before you leave! Now let’s sort out the tea and finger foods in the kitchen while you wait here, quietly and calmly!”
I was left alone for 10 or 15 minutes, as I heard clinks and laughter echoing down the hallway and through the open living room door. I caught the odd word, as their voices rose in glee. I was clearly the sole item under discussion and I longed to be with them right now, basking in their scorn. I’d just finished my bottle when I heard a car pull up the long drive way and the sound of female voices. The laughter was evident, as stiletto heels clicked up the path before the doorbell rang. I heard Jade head up the hallway and open the front door, as Jenny joined her and the sounds of cheery greetings were exchanged. I was barely able to breath as 4 new ladies were added to the group who knew my shameful secret.
The first lady, in her early 40’s, but still very striking gasped at my appearance. She was dressed in a smart leather mid-thigh skirt, black seemed stockings, 6” red stiletto heels and a red silk blouse. Next to her was a young lady of perhaps mid-teens, with dark hair and pink high-lights. She was dressed in a striking red dress, made from chiffon and indecently short. She wore a pair of black thigh-high stiletto boots, very shiny and wickedly spiked. Jade introduced them as Catherine and her daughter Allison. The second pair were equally striking, the Mother was again in her early 40’s, but was very tall and had a very wicked grin on her pretty face. Dressed in a simple L.B.D. with black seemed stockings and 5” black stiletto heels, she waved to me and made cutie-pie noises. Her daughter, Alexis, was very striking. She was as tall as her Mother, but was even more beautiful. Her eyes were very large and sapphire blue. Dressed in a tight white sheath dress, with white silk stockings and 4” stiletto heels, she was the first to approach me.
“Well hello, little sissy baby! My name is Alexis, what’s yours? Your name is Chrissy, isn’t that a lovely girly name for such a frilly pantywaist like you! I bet you’d like to be anywhere else, but right here and now, so don’t worry if you get frightened and have a little accident, because I’ve been led to believe that you wear great big diaper’s, don’t you? Why don’t you stand up and show us your diapers, as well as your lovely outfit and we’ll have a jolly good look at you! That’s it, let me help you, in case you fall onto your big bottom and make us all laugh! Wow, what a sight, you’re diapers are really huge aren’t they, so I guess you’re a messy sissy baby girl and you’re in need of complete protection! What does it say on your knickers, diaper filler that seems appropriate doesn’t it and that apron with that big cock and the word tasty, and does it mean that you’re a cocksucker, Chrissy? It does, well aren’t you a fag boy in a frilly dress and a frilly bonnet!”
I wilted under her verbal assault, as I felt my stomach turn over and a large spasm in my guts. I was very close to wetting my diapers, but I was more worried about having a bowel movement at any moment, in front of these happy ladies and shaming myself completely. Catherine joined me and ran her hands over my dress, under my petticoat and dress before caressing my nylon covered inner thigh. She looked down at me and asked if enjoyed using my diapers like a baby. I nodded my head, as she smiled at my response and told me that I was a very lucky girl to have found ladies of breeding to take me in hand. She tickled my bottom before sitting down next to me, on 1 of the high backed chairs.
Allison seemed the most wary of my dress, but when Jenny bought her over to me and had her take in my appearance at close range. She asked my babysitter if I really enjoyed being dressed this way and she told her to ask me instead. Jenny stood behind me, untied my pacifier and pulled out the penis shaped teat; a long piece of drool connected the end of my mouth with the latex teat. Allison looked me in the eye and asked me, directly, if I loved being dressed this way. In a lisping voice I told her that I needed to be dressed as a sissy baby girl, humiliated and degraded because I’m a little cocked faggot. I told the gathered ladies that I’d begged Jenny to dress me in such extreme clothes, so that there would be no doubt in their minds just what I was. Jade asked what that was and I told them that I was a pathetic loser, whose new wife was cuckolding me on our honeymoon, right at this moment and I deserved her utter disdain.
Jade asked her guests to sit down, while she and Jenny bought in the tea and finger foods, telling me to entertain her guests for a few minutes. Lauren took my hand, sat on a couch, next to her daughter and pulled me on to her lap. I sat there, my diaper acting as a cushion, as she proceeded to caress every inch of my nylon covered legs. Completely ignoring my presence, she asked Catherine what she thought about a man willing giving up all control over his life, including his toilet rights and submitting to unrelenting humiliation. Catherine thought for a moment and then gave her opinion that I was some kind of pervert in need of total humiliation, perhaps because of the lack in my manhood or maybe because I lacked a strong female presence in my c***dhood and now needed to regress as an adult. Lauren spoke to her daughter next.
“Alexis, I was very proud of your teasing of Chrissy and want you to know that I enjoyed your natural dominant nature in the presence of such nasty little sissy! He’s still shaking, like a naughty little girl told off by her mother and that’s the perfect tone for a girly like him! He’s such a pathetic excuse for a human being that I’m not surprised that he’s ended up back in diapers and I bet if you ask him if he’d like to sit on your lap! Go on, give Chrissy a cuddle, he smells like a baby, all baby powder and shampoo, so be prepared and maybe feel him up a little! You won’t think anything of it if my Daughter play’s with this sissy, sexually, I mean? No, well carry on dear and we’ll just pretend that your checking Chrissy’s diaper, for p*o! That’s it honey, just do what comes naturally and he’ll take anything you do to him, without complaint!”
I was pulled onto Alexis’s lap, smaller than her Mother’s, but just as warm and much more welcoming. She pulled my head into her chest, as she slowly edged her hand up my leg, under my plastic panties and inside my diapers. I was being felt up by a 14 year old girl, in front of her smiling Mother and 2 very interested ladies. Catherine asked Lauren if her daughter had a boyfriend yet and was told that she was still inexperienced with boys, so that this was her first time being sexually active with a “male”. Alexis entered my diaper with her small hand and found my chastity covered cock immediately. She asked me what I was wearing and I told her that I was locked away for ever, for my own good and was unable to reach any kind of sexual excitement with my tiny cock.
She smiled and asked me if that wasn’t terribly difficult. I told her that I was blessed to be able to replace my pathetic spurts with messing my diapers instead. I told her that felt much more fulfilled, doing my business in my diaper than I ever did spurting and wanted her to know that I was more than willing to never be released if I got to be trapped in diapers for ever. She smiled at me and commented that dressing in such pretty dresses and frilly knickers must be very exciting as well. I nodded and whispered that I loved being dressed in such outrageous outfits, especially very frilly petticoats. She was massaging my now empty balls, but she used her other hand to feel my petticoat.
She asked me what I loved about frilly underskirts and I told her that they felt divine tickling my legs and inner thighs. I admitted that I loved her touching my balls and that she was a quick learner. She kissed me on the cheek and told me that I was sweet, but that she thought that I was flattering her. I shook my head and explained that I was sincere, that she was making me feel all goosey. She chuckled and whispered in my ear that I was very naughty. She proceeded to squeeze my balls, tighter and tighter, until I grunted in pain and she pushed me off her lap. She told her Mother that I was a cheeky little girl and deserved to be punished for my effrontery.
Jade and Jenny entered the room then, carrying trays covered with all the necessary for a formal morning tea. Catherine told Jade that I’d been disrespectful to Alexis and was in need of a physical chastisement. Jade grabbed my arm, pulled me across the room and bent me over the back of a high backed chair. She asked Jenny to pass her some restraints, which she kept in a drawer and secured me to the chair. My knickers, tights, plastic panties and diapers were pulled down around my ankles, as I was displayed to the room. The ladies gathered around my naked bottom, as Jenny served them tea and finger foods. I was inspected by indifferent ladies, who seemed to be as intent on their tea as my punishment. Allison asked if she could be allowed the honour of discipling me. Jade told her that she should feel free to pick an instrument from a collection in a glass cabinet.
She opened the door and asked Jenny what all the instruments were. My babysitter pointed out an English cane, a flogger, a heavy wooden paddle, a long leather whip and a switch of birch branches tied together with a red ribbon. Allison asked which 1 would be the best to use considering she was a novice at corporal punishment; Jenny recommended the paddle as the others could cause real damage if handled incorrectly. She picked up the paddle and swung it against a sofa, causing an almighty noise. Jenny told Allison to aim for the middle of my buttocks and hit me as hard as she could. I looked back over my shoulder to the suddenly empowered young lady and prepared myself for my beating.
“Time for a well needed paddling, Chrissy and I intend to make you sorry for being so cheeky with a young lady! Now feel free to squirm and blubber, as I expect you won’t be able to help it anyway and take my discipline! Your bottom is very soft, sissy, and perfect for a hard punishment and you’ll be bright red by the time I’m finished! Do you mind if I check your crack for hidden surprises? Well I’m going to anyway, so there! It’s very loose back here; do you take it up your bum a lot, sissy? Maybe your wife or babysitter uses a big thick cock to stretch your hole like a slut or do you take real men’s cock like a whore?”
I nodded my head in reply, but Allison used my distraction to launch her assault on my bottom. She hit hard and soon built up a very irregular rhythm, not allowing me to anticipate her next strike. I cried like a baby, as my teenage torturer smacked my bum. The other ladies pointed out spots that she’d neglected, but I was unable to see where they were indicating, so I was surprised every time. The ladies were clearly enjoying my punishment, as they were laughing and egging Allison on. It felt like hours off my life, but was probably no longer than 10 minutes, so when it was over and I was untied, I fell to my hands and knees, bent my head down and kissed Allison’s thigh high stiletto boots in supplication.
Lauren pointed out that the original offence was against her daughter and shouldn’t I be abasing myself at her feet. I crawled over and continued my degradation. When the ladies had enough of my abasement they returned to their seats and began a conversation about my total lack of will power. Jenny told them about my morning stint licking her toilet, like a real pervert. The room entered a stunned silence before all the ladies clamoured for information. Jenny held up her hands and suggested a demonstration instead, but asked the ladies if anyone wanted to re-diaper me. Catherine raised her hand and I was soon lying in my back, on my changing matt, my chastity covered cock on display and my red bottom prominent.
Catherine applied cooling diaper rash crème to my throbbing bottom before powdering my derriere and pinning my diapers. Plastic panties, tights and rhumba knickers followed before I was lifted to my shaking legs. Allison and Alexis took me by my arms and linked their arms through mine before half dragging me out of the living room, upstairs and into the master bathroom. They were whistling in glee as they pointed out the gleaming white toilet. We were joined by everyone else and I was positioned on my hands and knees, in front of the toilet, surrounded by the bubbly audience. Jenny directed my latest public humiliation.
“Now then, Chrissy, let’s see you open the toilet lid with your teeth, but leave the seat down and then beg my Mother for permission to lick her toilet seat! Louder slut! We can’t her you and we definatly don’t believe you! That’s better, but I want you to understand just how disgusting this is, Chrissy and how repugnant you’re actions are! Now lick my Mothers toilet seat like the slut you are! God look at her go, she’s clearly loving every minute of her display for us, but maybe Chrissy should lick the inside of the bowl as well! Lift the seat with your teeth and lick the inside of my Mother’s toilet! That’s a good sissy, but maybe you should show us you piece de resistance and lap up some of the water, like a dirty whore!”
I debased myself for my audience and received howls of laughter. I couldn’t take the shame and lost control of my bladder. I wet myself, as I was made to feel like nothing, by my step-sister, her daughter who I yearned for, 2 strange women and their teenage daughters. When it was over I was left with Allison and Alexis, who just stood over me and giggled. I was asked if the toilet water tasted good and I cringed before begging them not be so cruel. They lifted me to my feet, took my arms in there’s and led me back downstairs. Instead of returning to the living room, I was pulled into a darkened room and pulled onto Allison’s lap. Suddenly a large screen T.V. came on and I realised that we were in a home cinema.
A movie started 1 that I recognised quickly, it was my wedding ceremony and I was forced to watch both my submission to Auntie Gemma, as well as her later spit roasting by her well hung lovers. The girls giggled, as I squirmed in shame as they pointed out that my wife was a total slut and that she loved every minute of her fucking. I lost total control and filled my diaper with my p*o-p*o. Allison knew in seconds, as I sobbed in shame, but she shushed me and told me to carry on watching. I couldn’t though and I begged her to please change my dirty diaper. Alexis heard and with a smirk on her face, she asked me if I’d really filled my diaper with a load and I nodded, a tear running down my cheek. I was pulled to my feet and led back into the living room.
Allison and Alexis held my hands, informing the room that I had an announcement to make. Teary eyed, I told them that messed my diaper and needed to be changed. Jenny grinned and asked if I’d gone number 1 or 2. I said both and she asked me if I’d enjoyed my nasty evacuation. I sobbed yes and Lauren asked what that meant, so I explained that filling my diaper was the only release of sexual tension I enjoyed now and I felt so ashamed of being such a pervert. Jenny pulled me into an embrace and hugged me tightly before bringing me over to the centre of the room. I was sat on the floor and asked if I’d like a particular diaper changer. I pointed to my youngest tormentor’s and the screamed yes. Alexis sat down next to me.
“Don’t worry sissy, there’s nothing to be ashamed of, after all you’re a baby girl in diapers and it would be odd if you didn’t mess yourself! I promise that we’ll be gentle, but we had better get started don’t you think! Now let’s have you on your back and pull your dress and petticoat out of the way. Lift your bottom Chrissy and I’ll pull your rhumba knickers down. There you go, but maybe Allison would like to remove your tights. There you are, now I’ll remove your plastic panties and diapers, so we can all see just what a mess you’ve made! Wow, what a pong and you’ve filled your huge diapers as well, but we’ll soon have you freshened up and inside a clean diaper! Lift your bottom and I’ll remove that ruined diaper!”
With everyone watching, glued to my every wince and sniffle, I was shown just how little regard for privacy is shown when a baby’s dirty diaper is changed. I was on display and the 2 teenage dominant’s milked every second. They chatted about how they’d never seen such a full diaper before and whether I was some sort of freak. I sobbed as Allison wiped my chastity covered cock and remarked that I clearly loved all the attention, as it twitched in her pretty hand and Alexis told her to watch what happened when she cleaned my bum. She coated her hands in baby oil and used loads of baby wipes to clean the cheeks before working inside of my buttocks. She slipped 2 of her fingers in my bottom and I sobbed. Alexis asked me what I was blubbering about and I quietly begged her to not stop her invasion of my hole.
Allison heard my plea, but the others couldn’t so she leant over, kissed me on the forehead and told me that they’d love to, but they wanted something in return. I asked them what I could do for them and the asked if I would speak to Jenny about allowing them to visit me at my home and see the full effect of 24/7 babifacation. They asked me if I would like it if they invited a few of their friends as well. I sobbed how many and they looked at each other before saying a dozen or so. In fact 1 of their teachers at school would be able to supervise a prolonged visit as part of a health and human resources class. I nodded my agreement and they frigged me off while my step-sister, niece and their Mothers looked on with glee.
I moaned at my treatment and Jenny realised what was happening. She knelt down and told the girls that my bum was clean enough; maybe they should diaper me now. I was pinned inside 4 diapers once again; a pair of pink plastic panties and my tights were raised before Allison pulled out a fresh pair of knickers for me to wear. Made of nothing more than sheer lace, they were see-through and utterly sissified. Alexis stood me up and I stepped inside my lacy prison. I was hugged by the 2 girls before Jenny took me by the arm and whisked me upstairs, into what appeared to be her old room. She asked me what I thought I was doing, allowing myself to be used as she used me without permission. I explained that I couldn’t stop them, but she was having none of it. She pulled me over her lap and she proceeded to smack the backs of my nylon covered thighs.
“Your bottom belongs to me, Chrissy and don’t you forget it, sissy! I’m in charge of giving you pleasure in your sissy pussy and I mean to teach you a lesson! Go ahead and cry, sissy, after all they’ve heard it all before, haven’t they! Heard you blubber and cry like a c***d being punished, so don’t pretend to have regrets now! I want an explanation about what you discussed with Alexis and Allison, sissy! They want to bring a group of their school friends to observe you being treated like the pervert you are, well that sounds like a grand idea, doesn’t it? A dozen schoolgirls watching you fill your diapers and abase yourself for the privilege! I’ll see if I can set it up for later in the week. Now that should see you until I can get you home! Now let’s head back downstairs and make our goodbyes, Chrissy be sure to lick each of our tea party guests shoes, in supplication!”
We returned downstairs and I went around each lady, licking the soles of their shoes, sucking on their stiletto heels before I thanked them for making me feel like a nasty sissy baby girl. I begged them to please remember that I needed to be treated this way because I was a small cocked loser and didn’t warrant being treated as a real man. I thanked Jade for hosting this lovely event, thanked Catherine and Lauren for their utter contempt for my plight and I thanked Alexis and Allison for changing my dirty diaper. I hoped that they would have the opportunity to do it again, soon, as being under the control of such strict young ladies was very appealing. I told them that I was in need of strict discipline and they had provided it.
Jenny attached my reins, led me out to my special van and strapped me into my push-chair. She left me for a few moments to say her goodbyes and we were soon off home. As we drove I told Jenny that I had felt so ashamed to be used by Alexis and Allison, sexually, but felt powerless to resist there domineering advances. I told her that I hoped they would be able to visit with their class soon, as I bet that being on display to a dozen schoolgirls, as she punished me, dressed me in humiliating clothing and had me fill my diapers for her amusement, would be so very kinky and degrading.
Jenny told me that I was a nasty pervert and that I should be ashamed to be degraded in such a very naughty and lascivious way. She asked me if I’d be willing to use my potty in front of the class and she laughed, reminded me that I had no choice and she would laugh at my public shame. She told me that I’d have to beg the girls to have my bottom cleaned and I would be spread eagled over my changing table, as a pretty you girl cleaned my dirty bum. She would film the whole encounter and I could present it to Auntie Gemma on her return as proof of my continued devotion to being a sissy baby girl. We pulled into home and we headed inside for some very painful discipline. I spent the next 24 hrs.’ being beaten over and over again.
3 days later Jenny heard from the teacher at Allison and Alexis’s private school. Her name was Miss Beckett and she had arranged for a dozen of her brightest students to visit our home to experience total submission of the male to female authority. Jenny arranged for the visit for the following afternoon and she spent the next day prepping me for our first home made movie. We set up a dozen hidden cameras, at strategic points around the house, in particular my nursery and bathroom, as well as Jenny’s toilet and bedroom. Jenny had me eating lots of vegetables, the night before and dozens of bottles in the hour before their arrival time.
I was kept un-diapered and in frilly little girl knickers, by Jenny’s order and banned from using my potty or any of the toilet’s. I would only be allowed potty privileges after the girls arrived. I was dressed in a pair of white silk stockings, held up by white ribbons tied around my upper thighs and a large white silk baby bonnet. On my feet was a pair of white silk and lace booties, as well as a white silk bib tied around my neck and displaying the phrase “CAN I SNIFF YOUR PANTIES?” My hands were encased in white silk mittens, joined together behind my back, effectively stopping me from using my hands or removing them.
A large pink pacifier was strapped into my mouth, a 3” rubber cock forced down my throat and I was tied over my changing table, my legs spread wide, allowing Jenny full access to my sissy pussy. She slowly forced an 8” long and 3” wide butt plug inside before pulling up my panties and giving me a hard thrashing with a whippy cane on the backs of my thighs. Jenny concentrated on the gap between my panties and the tops of my stockings. She didn’t stop for over 20 minutes and it was only the doorbell ringing, to announce the arrival of our guests that stayed her hand. She headed downstairs, as sobbed in agony at her punishment. I heard lots of excited voices coming through the house before I heard Jenny’s voice clearly saying welcome to my nursery.
I heard gasps, as a dozen schoolgirls took in the bizarre sights in my nursery, the clothes, diapers, furniture and most importantly, me. I heard them approach my sobbing body; quietly before a voice I recognised ask what I’d done to deserve such treatment. Alexis came into view and winked at me. Jenny answered with no hint of pity or compassion telling the gathered girls that I’d been a good girl all morning, but that she’d decided that I needed to be punished for simply being a sissy baby girl. She picked up her cane and very lightly continued my punishment, while explaining my predicament.
“Chrissy is a pathetic small cocked loser that was taught just how little he mattered to all women and what he deserved for trying to a real man! Right now, Chrissy is plugged at both ends, 1 to stop him from spurting forth a load of crap and the other is deep inside his bum! He’s been over fed on baby food and lots of yummy milk, but he’s been banned from using his usual toilet, a set of massive diapers, instead he has to get the permission of every member of your class to fill up his over-sized potty! He’s also going to go right in front of you all and that’s just so humiliating, isn’t it Chrissy? Doing your business in front of all these pretty girls, but we don’t care if you’re embarrassed, do we? No all we care about is making you suffer the most public and intense levels of humiliation possible! Now let’s un-strap you and you can show everyone you tiny cock!”
I was set free before being helped to stand up straight, in front of a dozen young ladies in school uniform and 1 very stern looking teacher. I lowered my panties and the girls gasped at the sight of me locked away in chastity. Jenny explained that I had no need of such a pathetic cock and I’d been locked away so I could concentrate all my attention on being a sissy baby girl. 1 of the girls asked if it hurt me and Jenny remarked that she didn’t care. In fact she explained that not only was my cock useless I was perfectly willing to be ridiculed for my lack of a real cock. Jenny asked them to form a line and take a few moments to play with my chastity covered cock, making sure to introduce themselves to me.
The first girl was very eager and grabbed my cock without delay. She told me that her name was Rita and that she’d never seen such a tiny cock before, even her 18 month old brother was more impressive. Second was a smiling dark haired beauty called Rachel. She looked me in the eye and asked me if I needed to go potty. I nodded and she laughed, telling me that I would have to hold it. Third was Olivia. She asked me if I liked being such a sissy, when I nodded she laughed and told me that she’d be honoured to teach me the true meaning of humiliation. The fourth was a blonde called Natalie. She looked me up and down before asking me if I really wanted to sniff her panties. I moaned and she called me a pervert. The fifth was a Latin looking knockout called Megan. She just looked at me with a half-smile that didn’t reach her eyes. I knew she would be trouble.
The sixth was a girl next door type called Katy. She told me that I was a cutie and promised to make me feel like a complete and utter sissy. The seventh was called Jessica. She leant in and whispered that she liked the look of my stripped upper thighs. She promised to give me worse later. The eighth was called Eva and she was hell on wheels. She gripped my balls in a vice grip and offered to remove my useless piece of meat. The ninth was called Emilia. She looked at me with utter contempt. She didn’t touch me at all and walked past me to inspect my dresses. The tenth was called Ashley and was a ball of energy. She told me that I’d be in for a very busy time under her tutelage.
The eleventh and twelfth girls were Allison and Alexis. They kissed me on each cheek and reminded me of our earlier encounter. Finally Miss Beckett approached and looked me over with a cool gaze; she rubbed my throbbing thighs and squeezed my bum, through my panties. She told me that I was in need of a very big enema to show me just how dirty I was. A massive douche of warm soapy water to give me perspective about my failed attempt at being male and to show me just how much further I could still go. Jenny took me by hand and bought me back together with the 12 schoolgirls, who were checking each piece of equipment and clothing in my nursery. They were giggling and were on the verge of losing control. Jenny quieted them down and asked them if I should be put into a pretty dress for their amusement. A chorus of positives followed and was soon being handed dress after dress.
“I think Chrissy should follow the theme of the day and dress in a lovely schoolgirl’s uniform, don’t you ladies? Ok then, we have the just the thing, indecently short and covered in frills, but it might be very embarrassing for him to wear it with you all watching, so how about we ignore his feelings altogether and make him cringe! Here we are, a short pink check skirt, with a built in petticoat and a sheer blouse with a pink latex tie, is it alright ladies? Well the let’s get the cutie-pie dressed and under control. Panties off and bib gone, now the booties and mittens before we find some lovely girly lingerie for our naughty schoolgirl! Pass me those white silk and lace knickers Emilia, they’ll look divine under his skirt. A pair of sheer white nylon knee length socks, held up by some pink lace ribbons and some black patent leather Mary-Jane’s! Dressing time, Chrissy and I think I’ll let the girls have the pleasure of dressing you this time!”
In moments I was surrounded by 5 or 6 giggling girls who took great pleasure in dressing me in my schoolgirl uniform. My panties were pulled up my legs and settled in place over my chastity covered cock and plugged bottom. Next were my nylon socks and shoes before. Alexis had me step into my skirt. Finally they buttoned me into my see through blouse and I was dressed. Jenny asked the girls to do my hair and make-up. I was turned into a slutty young tart with heavy make-up and blonde pigtails. I was sprayed with loads of perfume and bought back to Jenny for inspection. I was deemed suitable before she asked what they thought I should do for them now.
Ideas were tossed backwards and forwards until Rachel suggested that I should be made to plead for a nice hard strap-on fucking in my sissy bum. I looked at Jenny for guidance, but she smiled and told me that I was here to show these future leaders of the country just how far they could push their control of the male through sexual manipulation. Miss Beckett picked a large strap-on from the shelf, black latex, 9” long and 3” thick. She passed it to Jenny and deemed it suitable. She looked at each of the girls sizing up her choices before pointing to Megan. She looked like the cat that got the cream and was quickly removing her skirt before stepping into that big cock.
I was pulled over to the high backed chair and had my wrists tied to the top of the back. I was forced to bend over and stick my bottom out. Jenny sat on the chair backwards and looked me in the eye. She told me that I would be split wide open and she wanted the best view of my pain. Megan stepped behind me and began to caress my pantie covered bottom. The schoolgirls stood watching the unfolding scene with desire in their eyes. A palpable atmosphere of lust was in the room as I asked Megan to please stop teasing me. She laughed and told me to shut my slutty mouth. With a languid ease she pulled my panties down around my knees before kicking my legs apart. I was wide open for my fucking but I was still plugged up tightly. Jenny reached around and pulled out my plug and I was ready for a hard fucking.
“Your bottom is just the right size for a nice deep fucking, Chrissy and I’m the right girl to do it! I want you to know that all my friends will be watching your cries of agony, but I bet they soon turn to cries of pleasure when I hit your sissy spot! Every sissy has 1 and if you fuck them deep and hard enough they become completely unglued! You’ll be unable to stop my thrusts into your tight pussy and I’m going to teach you just what a 15 year old girl can do, Chrissy! Now I’ll just lube up your bottom and my cock before I **** you in front of my classmates! Here comes the choo-choo train, sissy!