Becoming Amy

Becoming Amy

By [user]Alhana Escher[/user]

I had been dressing up in women’s clothes since I was a k**. Started with my s****r’s clothes, I loved her school uniform. I used to prance around in it when I was lucky enough to have the house to myself, which wasn’t often. I loved pretending I was a school girl, and a rather naughty one at that. I’d pretend I was flirting to a guy, usually an older guy. I’d slip my hand up those pleated skirts and rub myself through her cotton knickers while imagining it was his hand until I was about ready to cum. I’d then dash to the toilet take my cock out and finish myself off, shooting into the bowl being careful not to get any on her clothes. I’d then take it all off and return it to where I found it. I was always good at remembering exactly where to put them back. No-one ever seemed to suspect anything, so must have done a good job.

After my s****r moved out I lost access to the school uniform I so loved so much, but now it was just Mum and me, so that meant more time alone in the house, and a whole new wardrobe to explore. Mum’s clothes were so much sexier than my s****rs, though for me still nothing beats a school uniform. Mum’s clothes though were so much silkier and lacier. She also had stockings which my s****r never wore. So now instead of a school girl I would dress up in my mum’s shortest and sexiest outfits. Now instead of cotton knickers and knee socks it was silk knickers and lace top stockings and suspenders. The skirts and dresses were shorter too, and with mums knee high leather boots or strappy heels I looked a right slut. Especially once I started playing around with her make-up. I’d seen her putting make-up on quite a few times, and I’d been taking mental notes.

My attempts back then weren’t really that bad, a bit heavy and clumsy, but the end result looked very slutty, which was perfect for what I was going after. About that time I discovered what pleasures I could gain playing with my bum. It started with just my finger. I’d slide it up to about the second knuckle and rub that oh so sensitive spot that always made me cum so hard. One day I even made a rather naughty discovery. Right at the back of the top of one of mum’s wardrobes, under a bunch of old junk that hadn’t been touched in years was an old vibrator. Nothing overly kinky like you can get today, just a plain, smooth, slightly pointed vibe about 5 inches long. It was covered in dust and the well out of date batteries had started to leak. It was clear it hadn’t been used in years. So I saved my pocket money and bought some condoms and batteries. The first night that I had the chance I dressed up in the sluttiest outfit I could find, made up my face like a cheep prostitute (not that I knew what one looked like back then, but that’s what it basically looked like) and tied up my long, budding rocker hair into pig tails. I pranced around in front of the full length mirrors on my mother wardrobe doors flirting with some invisible guy. I got down on my knees and took the vibe, pretending it was his cock which I took out of his trousers. I sucked on it for a few minutes before putting a condom on it and getting on my hands and knees. I lifted my black layered skirt, pulled down my silk, lace trimmed kickers and slowly worked the vibe into my arse.

It took a little while getting it all the way in, but once it was and it felt comfortable inside I started to slide it in and out. Slow at first, but picking up speed, slowly, but surely. After not too long I was fucking myself with it quite hard and fast. My cock was so hard and was pushing and rubbing against the silky material of the knickers. Before I knew what happened I was Cumming, shooting my sticky seed inside those silky knickers that I’d never thought to free my cock from. After all, I wasn’t playing with it; I was fucking myself like a proper girl. I was shocked, but so turned on too. I pulled the knickers off so as not to get the cum on any of the other clothes. I knelt there a few moments looking at the pale sticky mess inside those black silk panties. At first I just wondered how I was going to clean them up, but soon that turned in to wondering what it tasted like. Then suddenly I was licking it up, swirling it around my mouth and swallowing it. I licked and sucked as much up as I possibly could then started to clean up. Taking off the clothes and putting them back, except the stained panties. Disposing of the condom and returning the vibe and washing my face of the make-up. Just as I was finishing up I heard a car door close outside and just knew it was Mum. I dashed into my room and into bed naked, stuffing the soiled panties under my pillow just as she walked in the door. She came up to me to check I was alright and say good night. My heart was pounding the whole time, I couldn’t believe how close I’d come to being caught and hoping I’d got everything put away just right as I’d had no time for my usual double check. After leaving my room I heard mum go to the toilet and then to her room. She spent a few minutes in there before going down stairs. I’d got away with it.

Once I knew I was safe I took the knickers from under my pillow and put them back on. To this day I still don’t know why. Maybe after my near miss I was feeling uncatchable, or maybe I wanted to be caught. I just don’t know. I had plenty more nights like that night, without nearly getting caught that is. I’d always stash the soiled knickers till I could wash the stain out as much as I could before putting them in the laundry basket to be washed properly. I never got caught and soon I out grew my mothers clothes as within a year I was over a foot taller than her. Some time later, after getting a computer I made some friends online who also liked to dress. One was kind enough to send me some sexy knickers in the post. I took to wearing them every night to bed. But then I met Samantha. We fell in love quite quickly and eventually moved in together.. I was too scared to tell Sam about my dressing so I stopped; after all, she wore enough sexy clothes for the both of us. At least, that worked for a while. After about a year of marriage Sam was spending more time visiting friends and my urges to dress were growing again.

I started to buy myself some clothes to dress in. First it was a pair of pink frilly knickers and matching bra. I wore them a couple of times when I was home alone, hiding them away in an old briefcase when I wasn’t wearing them. Then I bought some white stockings with a ring of ruffled lace round the tops with a pretty pink bow. And a pink lace suspender belt. The colour didn’t quite match the knickers and bra, but it was close enough. A few weeks later I saw a really short pink and black tartan knife pleated skirt in a shop window and I just had to have it. I bought a white blouse at the same time. I didn’t wear them straight away but stashed them in the briefcase with the rest. Before I was prepared to wear them I knew I needed shoes to go with them. That took me months. I’d constantly looked, and though I kept finding ones that would go perfectly the stores never carried them in my size. I took to looking online and soon I found the name and address of a shop that was fairly near to me that specialized in women’s clothes in men’s sizes. They had lots of lovely pairs of shoes but were so expensive. So I saved some money up on the side and bought a pair of black patent leather high heeled Mary Jane’s. On the way home I stopped in a local sex shop and bought a 9 inch dildo and a bumper box of condoms. I got home that day a little before Sam so the condoms and dildo went in the case, which was now almost bursting with my secret girly stash, and hid the shoes just inside the attic where I knew Sam would never go. That night I told Sam I was going to visit my mother. I had no intention of actually going but knew Sam would take the opportunity to visit one of her friends.

I barely slept that night. I just kept imagining what I’d be doing the next day. So instead I ended up tossing and turning till morning, which agonizingly crept in. But eventually it did come. Sam rolled over on the verge of waking and I just stared at her beautiful face. Well, beautiful to me at least. She may have been on the larger side with a slightly round face, but to me she was beautiful. At that moment I wished I could tell her everything, my years of dreaming of being a girl and what I had planned. But that little voice at the back of my head kept telling me not to. That she would freak out and we’d be finished. Her eyes fluttered open sl**pily and she smiled up at me.

“Morning baby.” She mumbled with that sweet smile. I couldn’t help but lean in to kiss her. I loved her so much and hated having to lie to her. But lie I knew I must or have to bury a big part of myself for good.

“Morning sweetheart,” I replied after the kiss. “sl**p well?”

I already knew the answer as I had watched her almost all night and she had slept like a baby. But I could hardly let her know that or she would know something was up, so continue the pretence I must.

“Yes thank you baby, you? She asked.

“Yeah,” I lied. “Not too bad.”

“What time is it?” she enquired while rubbing her eyes. I rolled over to look at the clock.

“Just gone half eight.” I told her.

“Hadn’t you best be getting ready then.” She asked. “You know how your mother gets when you are late.”

“Yeah, I know.” I sighed rolling out of bed. “Mind if I shower first so I can get going?”

“Go right a head, “She said with a little giggle. “Give me another 10 minutes lay in.”

“You naughty girl you.” I chuckled on my way out of the room. I showered and washed my hair quickly and had a quick shave. As I returned to the bedroom Sam was getting up. “All yours.”

“Thank you baby.” She said as she shuffled out the room.

I dressed in whatever was easiest to find and dried off my hair as much as I could before tying it back into a hasty ponytail. As I left the bedroom Sam was just coming out of the bathroom with her towel wrapped round her body. I hugged her and gave her a long slow kiss.

“So, I’ll meet you at the station about 6 then.” I said, confirming the plan we had made the night before. “We can get a Chinese on the way home.”

“That sounds nice.” She replied. “I will probably be too tired to cook tonight. Janie says she is dragging me up town for a big shopping trip.”

“Sounds exhausting” I chuckled back. “Just don’t tire yourself out too much.”

“Oh, don’t worry,” She giggled. “I won’t. Have plans for you tonight. I know how much your mum can stress you out.”

“Mmmmm, Look forward to it sweetheart.” I replied, which was a huge understatement. After what I had planned for today I knew come tonight I would be as horny as hell. I kissed her once more. “Well, you have fun my love.”

“And you don’t have such a bad time!” She replied with a smile and turned to head to the bedroom. I went downstairs and to the front door, grabbed my coat and headed out. It was a brisk morning outside, but not too cold. I took a short walk down to the junction at the end of the street. The shops there were just opening so I crossed over the road and headed to the shop that seemed to have the best view up our street. It was a pet store. I headed in side and started to browse all the while keeping an eye out the shop window so I could see when Sam left.

It seemed like forever I wandered round that shop and I started to get some strange looks from the staff. Eventually though I saw Sam leave and head up the other end of the street toward the train station. I felt guilty for having hung around inside the pet shop for so long that I had to buy something just to make it seem I’d been in there for a reason. I picked a thick black leather dog collar and took it to the counter to pay then left and headed back home.

Once inside I ran straight upstairs. I quickly grabbed the ladders and retrieved my stashed shoes from the loft and then into the bedroom. I quickly stripped off my clothes and grabbed my electric shaver. I shaved off the rest of my stubbly body hair. Both Sam and I preferred to be smooth all over, which was somewhat of a blessing. Though, I did have to keep on top of mine much more frequently than she did. Once I was all smooth I went to Sam’s drawer and grabbed her make-up bag. I turned the radio on and turned it up quite loud before sitting down to paint my toe nails and finger nails then relaxing back on the bed while I waited for them to dry. After about 10 minutes they seemed dry and I got up again. I opened up my bulging briefcase and removed my clothes and toy from it. I put on the nylon stockings, slowly pulling the thin delicate material up my freshly smooth legs one by one. My cock was already beginning to get hard but I refused to pay it any attention. I then put on the suspender belt and attached the straps to the stocking tops. Next came those oh so cute frilly pink knickers, which I tucked my thankfully now soft again cock into. Then the bra, which I fastened at the front, then swivelled round the right way and put my arms through the straps. I took a moment to check myself out in the mirror. It looked sexy, but not quite right. The smallest size I could find the matching bra in was a B cup and those small lacy cups were just hanging lifeless on my chest. Then I remembered Sam had something I could use to fill them out. It took a little searching but eventually I found them. They were a pair of bust enhancers that looked more like a pair of uncooked chicken filets than anything else. I slipped them into the cups which filled them out quiet nicely. Not perfect by any stretch, but they would do. I made a mental note to look into buying some proper breast forms when I had the chance.

Next I put on the white blouse. I had forgotten till then just how tricky it was to fasten buttons up the other way round when you are so used to doing it the boys’ way. But eventually I managed it, and without too much of a fight too. I guess some things you never forget, just like riding a bike, it may take you a while to get to grips with it again, but the knowledge never goes away. I retrieved a tie from my wardrobe. I had at first considered using my old school tie, but I didn’t think black and green would sit well with the pink so instead went with the pale pink and grey one my mother had bought me a few years back. It hadn’t seen the light of day, till now. I tied it into place then put on the skirt and fastened it. Finally came the shoes.

I stood up and checked myself out in the mirror once more. From the neck down I almost looked like a slutty teenage girl. My skirt barely met my stocking tops and my fake bust stretched out the front of the blouse. I hadn’t figured that into the size choice when I bought it. Now came time to sort out the face. I sat at the dressing table and started on the make-up. Again, something I hadn’t done in years, but at least now I had the benefit of time on my hands so could try and do everything right. I Used Sam’s moisturizer first, as I’d seen her do countless times then went through her foundations to find one I that matched my skin tone the closest. After the foundation I put on some black mascara and some blusher to my cheeks and finished off with some baby pink high gloss lipstick. I wanted to try some more but didn’t quite feel comfortable doing so yet, and didn’t want to ruin what I’d already done. So instead I brushed out my hair and tied it into pig tails using a couple of pink ribbons from the little bowl containing all of Sam’s hair ties.

I returned to the mirror once more to admire my work. The view that greeted me caused a stirring underneath my skirt that started to make my knickers feel very tight. I wasn’t prefect, and the face would spoil any chance of being passable as a real girl. But then and there, it was enough. It was a little plain as I hadn’t thought about accessorizing at all, but then I had a wicked thought. I picked up the little bag I had discarded along with my clothes and pulled out the dog collar I had bought out of guilt that morning and put it on, struggling to fasten the strap behind my neck. One more look in the mirror told me that was enough. I looked like a very bad girl, and felt like one too. One of my favourite songs came on the radio and I couldn’t help dancing, a little unsteadily on the 3 inch heels, but with plenty of twirling to make my skirt float up and out to give a flash of my panties hidden underneath.

When the song had finished I knelt beside the bed and grabbed the dildo. I held it in one hand and started licking it and sucking it as though it were a real cock. I did all the things that I remembered Sam doing to me when she gave me a blow job, like licking round the head and down the underside and sucking it deep into my mouth till I was virtually gagging on it. My free hand had snuck down and under my skirt. I pulled the knickers down at the back to give me access to my hole while leaving my now hard cock straining against the material at the front. I worked my fingers in and out of my ass, first one, then two then finally three. After what must have been half an hour of just sucking the dildo and fingering my ass I knew I wanted more. I opened up the condoms and deftly slipped one over the dildo and climbed onto the bed.

I lay down on my back and bent my knees, placing my feet kinda flat on the bed. I closed my eyes and reached down with the dildo and started rubbing it against my slightly stretched little hole. I worked it in slowly, inch by inch. Moaning loudly as I stretched to accommodate it. Once it was fully inside I wiggled it around sending an amazing sensation through my body. My cock tented out the front of my knickers starting to get them damp with my precum. I began to fuck the dildo in and out of my ass, slowly at first, but picking up pace. I began to moan and call out, begging some unseen person to fuck me harder. I was totally lost in my own little fantasy world. But that came to a very abrupt end.

“Oh my fucking god!” It was Sam’s voice. My eyes snapped open and my legs went flat against the bed with the dildo still buried deep in my ass. I hastily tried to cover myself up as I sat up.

“This,” I faltered then started again. “This isn’t what it looks like sweetheart!” I blurted out starting at my stunned wife standing in our bedroom door in her rain coat. I had be so wrapped up in what I was doing I hadn’t heard her come in, and so horrified at being caught I didn’t even wonder what she was doing back so early.

“Oh really?” She demanded glaring at me. “So my sissy husband isn’t dolled up like a cheep whore fucking his ass with a dildo and calling out for someone to ‘Fuck him hard like the little slut he is’ then?”

“I, I...” I couldn’t think of what to say. How to explain myself. “I’m sorry. I, I can…”

“Can explain?” She shouted cutting me off. “Can you really? Well lets she how well you can explain then!”

She stormed over to the bed and reached for me. I closed my eyes expecting her to slap my face or something but then I felt a tugging at my neck. I opened my eyes as she started pulling my off the bed by the D ring at the front of the collar that I had completely forgotten I was wearing. She pulled me off the bed and out the room and started heading for the stairs. The dildo still buried in my ass had only slipped out slightly before it got caught by the knickers bunched up just below my bum cheeks. I began to panic, where was she taking me and what was she going to do.

“Sweetheart, please stop,” I begged as she dragged me down the stairs. “Let’s talk about this, let me explain.”

“Oh you can explain all right!” She said looking over her shoulder at me with an evil glint in her eye as we reached the bottom of the stairs and headed toward the living room. “Let’s just see how well you can explain. Alex, look what I found”

It hit me like an out of control bus, even before I saw the man standing in the living room. Sam hadn’t come back to the house alone. But who the hell was Alex? I had never heard her mention him before. It didn’t take long to find out as just a moment later we entered the living room and there he was standing there dressed in leather trousers and shirt. He stood a few inches taller than me and had a few more pounds worth of muscle over me. I could feel myself turning very red.

“Oh Sammikins,” He gasped as he saw me. “You told me that hubby was a bit of a wimp, but you never said he was a complete sissy slut!”

“That’s because I didn’t know,” she chuckled at the dark haired man I had never seen before. “I just found him like this in our bedroom. Check this out!”

She quickly spun me round and lifted up the back of my skirt, not that it needed much lifting to clear the bunched up panties. I was so mortified at being caught and dragged in front of this man like this that I did nothing to stop it. I just stared down at my feet. The strange man’s response though, was enough to remind me of the dildo still buried in my arse.

“Oh my!” he exclaimed. “That looks like quite a big toy in that sissy pussy! And such cute sissy panties too.”

“Oh yes,” she laughed. “The little slut was ramming it into her bum so furiously she didn’t even notice me enter the room. She just lay there begging to be fucked harder.”

“Oh really?” He enquired with a chuckle. “Reminds me of a certain other little subbie slut, ah Sammikins?”

“Oh, but at least I’m a slut for real cock Sir,” she giggled in reply. “Or at least for toys used on me by other people… Well, by you Sir.”

That was enough to snap me out of my self pity and embarrassment. Suddenly what my wife and this man were saying was sinking in. They aren’t just a couple of friends who had happened to meet up. She was having an affair with him, and she had called him ‘Sir’. What the hell was that about? My head flew up and I spun round to face my wife who was still laughing with a slightly red face.

“What the fuck?” I asked loudly. “Have you two been…?”


I didn’t even see it coming, but Sam’s hand was just suddenly there, connecting with the side of my face, knocking me sideways slightly and setting my cheek on fire. Tears welled in my eyes almost immediately and I just stood there staring at her, right into her eyes. For the first time I really paid attention to them. I could read Sammy like a book just by looking into those eyes and what I saw now shocked me so much I couldn’t move or speak. Suddenly everything made sense. How could I have been so stupid? Underneath her anger and hurt at my outburst I could see something I never expected to see. A little bit of amusement and a lot of lust. It was that same look she always had when she came home feeling horny. That same look she had when we had the most amazing sex we could have.. Early in our relationship we had experimented a little with the kinky stuff. Sam would try getting me to tie her up, or spank her. I of course obliged but nothing seemed to really work. Mainly, I believe now, because all the time I wanted to be the one to be tied, spanked and dominated. We gave up after a few tries. Soon after that was when Sam had started visiting her friends more, and coming home horny. I realized that each time that had happened she must have come back from visiting him. He must have got her all worked up and sent her home to me. He was her Master. He gave her what I could not. And at that moment, I couldn’t blame her. In a way, wasn’t that exactly what I had been doing? Sam broke our eye contact just as a really evil look started to fill those deep blue eyes. She turned to her Master smiling.

“I’m sorry Sir.” She said to him in a very soft, calm and respectful tone. “I’m suddenly not feeling very submissive. But I don’t think you will have a wasted trip Sir, I know you love your sissies as much as you love real girls. May I?”

Sam gestured to her Masters bag that sat on the table behind the couch. He just smiled back at her and nodded. I stood there feeling exposed and vulnerable. Again I just looked down at my feet. For the first time I became aware that my cock was still straining at my panties. How could I still be rock hard after everything that was going on? Sam went to the bag on the table and opened it up. She rummaged inside it and pulled out a pair of pink shiny PVC cuffs. She turned and walked back to me.

“Give me your wrist you little slut!” She spat at me. I looked up at her and saw no malice in her eyes, only a mischievous amusement. I lifted one wrist and she quickly fastened a cuff to it and gestured for the other one. I obliged quickly. The stinging still my face told me not to argue. She fastened that one in place and clipped a double ended belt clip to its little D ring. Grasping my wrist she spun me round and grabbed my other wrist and snapped the other part of the clip to the D ring on the other Cuff.

“You want to act like a little slut,” she said as she spun me round to face her once more. “Then I’ll make you be a little slut!”

She hooked her finger into the ring at my neck once more and dragged me over to her Master. She pulled downwards forcing me to my knees if front of him. I looked up to be faced with his groin, and the large hard looking bulge in his tight leather trousers.

“This is a real man!” she told me. “A Master. And I’m sure if you do a good job today, he could become your Master too. You would like that wouldn’t you sissy?”

“Yes.” It was a barely audible whisper. I could hardly believe I had said it myself. Till now anything like this had only been in the realms of fantasy. I didn’t know if I could do it for real. But now, I couldn’t wait. His cock looked huge, and so close to my face. I wanted to taste it so much.

“What was that sissy?” She demanded. “I didn’t hear you.”

“Yes.” I spoke louder this time, but with a shaky voice.

“That’s yes Miss you little slut!” She slapped my face again as she spoke, relighting the fire in my cheek.

“Y-yes Miss.” I stammered in reply.

“Much better.” She spoke with a hint of pride in her voice. “So Sir, Do you think this sissy slut could please you today Sir?

Alex took my face in one hand by the chin and tilted it up to face him so he could properly study my face. He smiled at me as he tilted my face from side to side getting a really good look at me.

“Hmmmmm, she needs a lot of work,” he said thoughtfully. “But I’m sure you can manage to do that for me. But yes, I do think the little sissy slut will do rather nicely for today. Lets she how she manages with a real cock shall we?”

“Yes Sir,” She replied. “She sure does seem hungry for it.”

Sam knelt down beside me and unfastened Alex’s button fly. His cock immediately sprung out, nearly hitting me in the face. It was long, at least 10 inches, which was a bit longer than my own, but much fatter. Sam wrapped her thumb and forefinger round the base and pointed it straight at my mouth. Placing her other hand on the back of my neck part f***ed, part guided my face closer. I didn’t fight it, instead opening my lips and letting the head between them. I wasted no time in starting to lick and suck his large sensitive tip. Alex began to let out some low little moans of pleasure, letting me know that he was enjoying my ministrations to his manhood. Sam let go of my head to allow me to do as I wished. She just sat there holding his cock there pointing at me to do what I needed.

I began sliding his cock in and out of my mouth, licking at the tip and up and down the shaft. I had studied what Sam had done to me when she did this and intended to show her how much I had learnt. Alex’s continual moans let me know I was doing a good job which encouraged me to keep going. I started to take more and more of his cock in my mouth, gagging slightly when he would buck his hips at me forcing himself deeper in that I had intended. His two strong hands took a hold of my pigtails and started tugging on them, pulling me harder on him as he started thrusting at me, fucking my face. I just knelt there, unable to move sucking and licking that hard, thick cock as it slipped in and out of my hot pink lips.

I started to taste his salty precum begin to leak from the tip into my mouth and I licked it up hungrily. It was the first time I had tasted another mans juices, and I loved it. I let out a little moan of pleasure of my own and started to suck a little harder which urged he to fuck my face even more.

“Ohhhhh, Such a talented little sissy you have here Sammikins,” He moaned. “She sucks like a real pro. Have you been giving her lessons?”

“I didn’t even know she liked cock till this afternoon,” She laughed back at him. “But yes, it can’t possibly be her first time. I bet she has sucked loads of cocks, the little slut sissy.”

I started blushing as I sucked. Though it was my first time sucking a real cock, I loved the compliments coming from my wife and her Master. Suddenly he pulled his cock from my mouth and released my pigtails, taking a step backwards. I looked up at him worrying I had done something wrong. He just smiled down at me for a few moments before looking at Sam.

“Let’s see how good her pussy is!” He said grinning at Sam. “Prepare her for me!”

Sam took hold of the ring on my collar and stood, pulling me to my feet as she did. She pulled me the few steps to the couch and guided me to lie over the arm with my face on the seat and my legs splayed out dangling over the arm. Once I was in place she walked behind me and lifted my skirt. She pushed on the end of the dildo forcing it back deep into my bum causing me to moan loudly then yanked my knickers down to my knees. She took a hold of the dildo again and worked it in and out of my stretched hole a little before slowly withdrawing it. I lay there for a bit completely exposed to them with my face pressed into the seat of the couch.

I was just beginning to relax when I felt something cold and wet squirt between my cheeks around my slightly loose hole which was quickly followed by Sam’s fingers which worked it into my hole. Her fingers probed my butt working the lube all the way in. It felt so amazing that I started to push back against them a little.

“Get a load of this Sir!” Sam laughed as she worked her fingers in and out of me. “The little sissy is really gagging for it!”

“Ho oh yes,” Alex chuckled back at her. “I think we had best give it to her then hadn’t we?”

“Oh yes Sir,” Sam sniggered back as she slid her fingers out. “Let her feel a real cock in her sissy pussy.”

Sam moved round to the front of the couch and sat on the floor as Alex move behind me and started to get himself into position. I looked up into Sam’s face as she took hold of my hands and gave them a reassuring squeeze. I could see a quizzical look in her eye and knew the question immediately and gave her a little nod to let her know I was ok. She smiled at me the turned her gaze to Alex and nodded. Almost straight away his hard, hot member was pushing into me. It felt huge, larger than anything I’d had in there before, but also felt good. No, more than good, it was amazing. It slipped in so easily as I felt myself stretching to accommodate him. It hurt a little as he slowly slid the full length into me, but I didn’t care. My own cock was hard underneath me, trapped between my body and the arm of the couch. Harder than I remember it being in a long time. Sam just sat there holding my hand and smiling at me lovingly. I could still hardly believe this was happening.

“My god she is tight!” Alex gasped behind me. “I was worried she would be all stretched out by dozens of cocks from the way she was sucking me. This is just perfect. Virgin sissy pussy, there’s nothing finer!”

Sam snorted with amusement and squeezed my hands again as Alex then started to fuck me. Slowly pulling out and quickly pushing in. Each thrust in caused me to emit a soft low little grunt. This was so much better than a dildo. His hot cock filled me so completely I could feel every pulse and throb as he slowly picked up speed. Each thrust came quicker and harder than the last and grunts were getting longer and closer together till it was more like one long moan. It wasn’t long till he was fucking away at me hard and fast, ramming his big hard cock deep into me. He leaned forward and took hold of my pigtails again, this time pulling my head up and back. It hurt like hell and I screamed in a mix of pain and so much pleasure squeezing my eyes shut. Alex though didn’t even break his stride, if anything he got even harder.

“Oh yes you little sissy slut,” He grunted at me as she was plunging deep into my arse. “You like it like that don’t you?”

“Ohhhh yes Sirrrrr,” I heard myself calling out to him. “Yes sir fuck me hard like a little slut!”

Alex needed no encouragement however as he just pounded away at me. Sam just sat there smiling watching my face. I tried to fuck back at him, but bent over the arm of the couch as I was I found it impossible so instead I rocked my hips back and forth a little, making my cock rub back and forth against my skirt trapped between my body and the couch.

“Oh god yes!” He moaned as he kept riding me hard. “I’m gonna fill your pussy with my cum sissy! You want that don’t you?”

“Ooooo, yes Sir!” I cried back.

“Say it Sissy!” He told me. “Say you want me to fill you up with my cum! Beg for it slut!”

“Oh god, please Sir,” I pleaded with him. I could hardly believe the words coming from my mouth with my wife sat there right in front of me, but I couldn’t stop myself. “Fill my sissy slut pussy with your hot sticky cum. Squirt it deep inside my no longer virgin sissy schoolgirl hole and make me become a real little sissy slut Sirrrrr”

My outburst seemed to do the trick. Alex’s body went completely stiff and he thrust into one last time as he began shoot load after load deep in me. As soon as that first splash of cum hit me it drove me over the edge. I felt my own cock pulsing under me as my cum started squirting on to the inside of my skirt. I could felt my hole squeezing and contracting round his cock as we both came.

“Ohhhhhhhhh, fuck yes,” he growled at me. “Oh fuck that is so good sissy! Milk Masters cock with your pussy!”

We stayed like that panting for a while till our cocks had fully emptied their loads then he slowly withdrew from me with a sloppy wet sound as the head slipped out. I immediately felt his cum begin to leak from my sissy pussy and begin to dribble down my balls. I Just laid there exhausted, but happy. Sam smiled a loving smile at me then stood and went to her Master.

“Did she satisfy Sir?” Sam asked.

“Oh, She more than satisfied Sammikins,” he replied to her. “She was almost as good as you. Utterly amazing.”

“Is that right Sir” she chuckled. “Do you wish to own her too then?”

“I sure do!” he chortled back. “Very much so. But you will have to help her become a better sissy for our next meeting. She did an ok job, but she needs a lot of work. I’m sure you can set her straight.”

“I can manage that Sir.” Sam giggled at him. You would like that wouldn’t you sissy? Become Masters sissy sub slut and my sissy sub s****r?”

“Yes please.” Was all I could manage with a shaky voice.

“Good Girl.” She replied with pride in her voice. “Now go clean yourself up and go wait for me in the bedroom.”

I pulled myself up from position over the side of the couch and pulled my knickers up which started soaking all the cum up right away. I turned and headed out the room and up the stairs. As I was going into the bathroom I heard Sam calling up to me warning me not to get changed. I took a few moist toilet wipes and cleaned off the cum from inside the front of my skirt and my inner thighs and straightened my hair before heading into the bedroom. I got on the bed and lay back with my eyes closed trying to take everything in. When I awoke earlier that morning I had no idea that anything like this would ever have happened. But deep down I am so glad it did. It was as though all my darkest desires and dreams had all come true. After a few moments laying I heard the front door close followed by the sound of Sam coming up the stairs. I suddenly felt myself worrying about what she was going to say. She may have f***ed me to suck Alex’s cock and take it in my sissy pussy. But it was me that decided to dress up like a little sissy slut, and it was me that had begged to be used like a slut. How did she really feel about that?

“Hiya baby.” She said softly as she came through the door. “How are you feeling?”

“I, “I began then stopped. I didn’t quite know what to say. While I hesitated Sam crossed the room and sat down on the bed taking one of my hands again. “I’m happy. I think.”

“Only think?” She enquired.

“It’s just…” I trailed off unable to articulate my feelings.

“Just what sweetheart?” She squeezed my hand as she spoke.

“I don’t want to upset you.” I replied. “I don’t want to hurt you. I love you so much.”

“Upset me with what? Hurt me how?”

“With this!” I gestured at my clothes. “And what happened downstairs. I liked it, no, I loved it. I want to do it again, and do it lots. I never thought I did, thought it was just a fantasy that I could never experiences. But now I have, well, I loved it and never want it to stop. But I don’t want to loose you. I…”

“Loose me?” She gave a huge belly laugh. “Why would you loose me? You have done nothing worse than I have! In fact, I was the one getting it from another man behind your back. The guilt of it was all getting to be too much for me and today was going to be our last session. Finding you the way I did was just a shock. I’m sorry. I shouldn’t have done what I did. But, by the sounds of it, you aren’t sorry I did it.”

“I… no, I’m not.” I could feel myself turning bright red. “Did you really mean what you said?

“About what?”

“You know, us becoming subbie s****rs?”

“Of course I did silly!” She laughed. “I have wanted to share this part of my life with you since we first got together. But when I tried to make you Dom me I just assumed you weren’t into it. It didn’t even cross my mind that you were sub. But now I know… Well that just means the fun has only begun.”

“Thank you.” I flung my arms around Sam and hugged her tight sobbing with joy while my face pressed into her bosom. She folded her arms round me and gently rocked me. “Thank you so much.”

“Oh hush now you daft sod.” She said to comfort me. “No need for that.”

“I’m just so happy”

“Well, so am I.” She rubbed my back then gently prised me off her. “Starting tomorrow, we are going to have a lot of work to do.”

“Oh?” I asked.

“Of course,” She smiled that wicked smile at me again. “Master Alex said that next time he visits, Amy had best look like a proper girl and not a guy in a dress. Or we will both be in big trouble!”

The End?
98% (36/1)
Categories: AnalBDSMShemales
Posted by AlhanaCD
3 years ago    Views: 2,170
Comments (13)
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3 months ago
such a hot story thank you
1 year ago
Wow..... An amazing story!
1 year ago
love it
3 years ago
Great story!
3 years ago
Mmm nice I'll happily ask for more :D
3 years ago
Wow will be looking for the next chapter thanks Candi
3 years ago
Please write some more sissy sub stories, that was amazing!
3 years ago
I have a second part in the pipe line, not sure how long it will take before it's ready for posting
3 years ago
will there be more to this story
3 years ago
Will there be more to this story????
3 years ago
good story
3 years ago
Wow, this is great story! More.
3 years ago
very nice would like to hear more exploits!