The day begins at 4:30 a.m.. I am awakened by the alarm next to my bed on the floor in my tiny cell. It’s barely big enough for the old mattress I have to sl**p on, but it has been my bedroom for the past 8 or 9 years (I’ve lost track). Every day is basically the same. I wake up and crawl from my room to the bathroom at the end of the hall in the basement. Cameras watch my every move, so trying to cheat by walking (ever) is a no-no. The punishment is far worse than the crime, so I am always obedient. In the bathroom I administer several enemas, being sure to expel all the nasty waste from my b... Continue»
Sharon’s Mistress throws a Sissy Party
(Prior chapter is Sharon’s Sissy Saturday)
The next morning Mistress was kind enough to let me sl**p in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I crawled from my cell and saw a note from Mistress Angela telling me not to wash up but to dress as I was and make breakfast. I still reeked of cum and men’s piss, and my skin felt sticky in some places and stiff in others. Nevertheless I put on my maid’s uniform and heels and went upstairs to the kitchen. My collar was still on, of course, but I added a small harness that held a fat butt plug in my pussy and gave me a nice feeling of fullness. I took my time preparing breakfast so that everything would be perfect. I wanted to show my Mistress how happy I was to have this wonderful life as her sissy slave. In fact, I couldn’t imagine wanting any other kind of life. I had everything a gurl like me could want: security, someone who loved me and cared for me, someone who would use me and treat me like the slut I always knew I was, pretty clothes, shoes, a purpose in life (serving Her), and the thrill of always being on edge sexually, the thought of sex never far from my mind – ever. She kept me that way, with the hormones , the chastity/denial, and her constant reminders of my place in her life. What more could a sissy ask for?
After breakfast, Mistress announced that there would be guests coming over for the day – a Sunday afternoon party. It was her friend Diana’s birthday, and she was throwing her a party to celebrate. I knew better than to ask questions, just simply went about cleaning and preparing the house according to her instructions, still dirty as I was. Mistress Angela didn’t seem to mind. She would occasionally hold her nose when she was close to me, and make a remark about what a filthy slut I was, but that just added to my sense of humiliation and excitement. My little cock bell tinkled involuntarily whenever she would berate me or look at me with a mixture of lust and disgust. Clear fluid leaked down my thighs, further betraying my state of frustrated near-arousal.
The guests arrived around noon, showing up a few minutes apart. The first to arrive was Catherine with her sissy Jody in tow (literally). Catherine was a very regal woman, quite well to do, but she also had a big heart when it came to charitable causes. Three years ago, on one of her trips to the inner city to help deliver food and clothing to the homeless, she had come upon Joey, a 15 year old runaway, whose soft features, pale skin and red hair immediately caught Catherine’s practiced eye. She spoke kindly to him and asked him if he had a place to stay, offering to help him out if he would care to let her help him. He had reluctantly accepted, but when he saw the magnificent house she lived in and the room she had available for him, he fell in love with it and never questioned her or looked back. The room was very feminine, pink and purple, with a canopy bed and a frilly comforter. Catherine knew from looking at Joey that he was, at heart, a true sissy. Joey became Jody, Catherine’s devoted sissy, and lived a life few 15 year olds like Joey could imagine. He had been a delicate boy, effeminate, slightly built. His alcoholic stepfather came into his life when he was 11 and began abusing him almost immediately. He treated Joey like a little girl, constantly belittling him for his girly looks and effeminate actions, and after a year began to visit Joey’s room at night, using him like a girl. Joey hated it at first, but he became used to it eventually, and when puberty hit, he found he was conditioned to respond like a girl. He had never been quite sure he really was supposed to be a boy, so his stepfather’s treatment of him seemed almost natural. When the stepfather started beating him as he fucked him, however, Joey ran away, finding himself among many other homeless k**s in the city. His chance meeting with Catherine gave him a unique opportunity, and he happily became a lifestyle sissy, looking, acting and dressing girly, but still almost able to pass as an effeminate boy. Catherine liked the slim look, the freckled pale skin, the long red hair. She gave him just enough hormones to make his little breasts bud, but not enough to make him develop bigger, rounded tits like mine. He/she would always look like she was a young adolescent girl, who happened to have a nice little cock. I loved Jody. We always had fun together, so I was glad she was a party guest.
The next guests to arrive were Elizabeth and her husband, John. Only John was now Jennifer, a recently feminized man, whose wife had decided she really wanted a sissy/cuck instead of a husband. John had money and had not had to work, so when Elizabeth discovered his secret stash of porn with a heavy emphasis on female domination, she immediately started on a project of changing John into a private plaything. He didn’t object, much, but this was all fairly new, so he was still adjusting to his new role in life. He arrived in full sissy gear, a pink wig, a short frilly dress with petticoats, heavy makeup, stockings and very high heeled shoes which he was still learning to walk in. His ankles were chained together with a short length of chain, “to help him learn to walk like a sissy,” Elizabeth explained. He was also gagged. A pink leather panel gag across his lower face held a penis shaped gag deeply in his/her mouth. “Her voice isn’t quite as high and feminine as I want it to be…yet,” Elizabeth explained, “so it’s better if she doesn’t speak at all. Her eyes usually tell you everything you need to know. And her moans,” she added laughing. Jennifer also wore a kind of bib over her pink pinafore dress. “To catch the drool,” was all Elizabeth said when Mistress Angela asked about it. “The gag makes her drool like a little bitch, and it’s easier to let the bib catch it. Besides, she’s still a baby sissy, isn’t she? Show them, slut!” In response, Jennifer raised the front of her frilly dress and pulled up her petticoats, revealing pink satin panties with a telltale bulge in front. Elizabeth reached over and yanked the panties down letting them fall to the chain between Jennifer’s ankles. “My newest addition to her training,” Elizabeth said, as the other women noticed the stainless steel chastity device enclosing Jennifer’s cock. It was the elaborate kind with a sounding peg inserted into the urethra. “Bend over, bitch! Show them the rest!” Elizabeth’s tone was commanding. Jennifer did as she was told and turned around bending over at the waist, still holding her dress up in front of her. The women saw that the cage encircled Jennifer’s boi clit and sack; a steel rod ran from the base of her sack to her boi pussy making a 90 degree bend right there. “There’s a stainless steel ball about the size of a trailer hitch up inside the slut’s cunt,” Elizabeth said proudly. “She’s totally plugged right now. The cage went on three days ago. I made her masturbate for me one last time and let her cum on my shoes. After she licked it all up, I locked her in the cage. She’ll wear it for the next 6 months to start. I may make it another six after that. We’ll see. I may even have her balls cut off. It’s not like she’s ever going to need them again. And no more messy leaking! That little plug in front can come out when I let her pee, which is twice a day, on command. The ball in her cunt stays in 24/7 except when I let her shit, which is usually only once every other day or so. She may be a bit uncomfortable, but I don’t care. In a few weeks she’ll get used to going on command, and that will make my life sooo much easier!” she finished with a laugh. The other women joined in, patting Jennifer’s bare ass and fondling the underside of her little cock prison.
“Who else is coming?” Catherine asked. “Just Diana and Danni,” Mistress Angela answered, “In about an hour. She’s the guest of honor, so I wanted to be sure we were all here and ready for her.” Catherine ordered Jennifer to cover herself back up, and Mistress Angela clapped her hands, bringing me and Jody running from the dining room where we had been setting the table but could hear every word of their conversation. “Jody, I want you and Jennifer to give Sharon a bath before Diana arrives,” Mistress Angela said. “I’m sure your Mistresses won’t mind.” “Of course not,” Catherine and Elizabeth answered in unison. “And it will give us some time to catch up,” Mistress Angela added. “Run along now! And make sure you scrub her really well! You’ve probably noticed her stench. I took her to the shop yesterday. I think she did close to 250 men. Not a record, but close. Go clean her up, inside and out! See what you have to look forward to, Jennifer?” she added with a wicked smile.
The three of us sissies headed off down the hall to the bathroom, Jody practically skipping, Jennifer mincing her way as best she could given her high heels, ankle chains and general inexperience with both. There they filled the tub with hot water and floral scented bubble bath, removed my clothes, collar and butt plug, popped me in and scrubbed me from head to toe. The whole time Jody chattered on and on about all kinds of girly things, the new clothes in her wardrobe, her latest vacation trip with Mistress Catherine, some new shoes she was dying to get, and even the latest date that Mistress Catherine had arranged for her, a chaperoned affair with an elderly gentleman who was very fond of slim, ginger sissies. She talked about how kind and gentle he was, and how grateful he was to have her kneel naked in front of him at the end of the evening and suck on his penis. He had taken Viagra, which gave him some staying power, but Jody liked to think it was her girlish charms that really got him hard. He had even sucked on her little clitty as part of their fun, getting it hard in his mouth. She loved the way it felt to have the older man lick and suck her slender cock. She wasn’t allowed to cum, of course, just stay up, but that was enough for her. Under Mistress Catherine’s instructions, she had sucked her date for nearly a half hour, licking and sucking his balls into her mouth until at last he came. It wasn’t a lot, but Jody described how she carefully caught it all in her mouth and showed it to both her date and Mistress Catherine before swallowing it and thanking the gentleman for letting her suck him and for sucking her little clit (which was still standing at attention). Just describing the scene made her hard all over again, and she playfully made her clitty bounce up and down so Jennifer and I could watch. Neither of us could enjoy such a feeling, however, but I loved watching her play with herself. Jennifer just looked slightly miserable, wordless because of the gag, no doubt contemplating spending the rest of her life as a sissy-slut-slave-bimbo-castrated-cuckhold-plaything.
“Don’t you just love her titties?” Jody gushed as she bathed me. Jennifer nodded, and I thought I detected the response of the man she used to be in her longing look at my breasts. Jody loving soaped and rinsed my tits and paid special attention to my nipples. Then she leaned over and tongued them, sucking them into her warm soft mouth. I moaned with pleasure. In all my time in the booth yesterday, my tits had received no attention at all. With my hands locked behind me, I couldn’t even play with myself, so this was pure heaven. Jennifer squirmed uncomfortably watching this interaction between two sissy girls, probably due to her cock’s futile attempt at an erection in its confining cage. “I love these,” Jody cooed, continuing to lick and suck my tits. “Don’t get me wrong,” she blathered on, oblivious to Jennifer’s discomfort, “I love my own little titties, too! I just love to play with Sharon’s! They’re so…perfect!” Turning to Jennifer, she asked, “Are you going to get titties some day, Jen? Is your Mistress going to have yours done?” Jennifer nodded and made a slight moaning noise around the penis gag in her mouth. “Hormones?” Jody asked. Jennifer nodded. “Implants?” Jody continued. Again, Jennifer nodded her head. “Oooooo, lucky girl!” Jody bubbled excitedly. “I can’t wait to see them! And play with them! If Mistress Elizabeth will let me!” she added. “Is it true she’s going to have you…um…castrated?” Jody asked, the last word coming out as a whisper. Jennifer turned to her with pleading eyes, mute behind the gag. Jody smiled at her and went on, cheerfully. “If she does, that will make you girly so much faster! I have a girlfriend whose owner had her…done…and now she’s the sweetest most feminine thing you’ve ever seen! The only way you know she ever had…um…them…is that she has the cutest little clitty! It wiggles!” she said giggling.
When I stood up in the tub so the girls could wash between my legs, Jody turned me around and asked if I would bend over so she could clean my pussy. When they saw how stretched I was, Jody gasped, and Jennifer just moaned. “How many men fucked you yesterday?” Jody asked. “I don’t know,” I answered. “I lost track. I tried to count them but after the first couple of hours I realized I had missed a few and then I couldn’t remember. It was a lot, though. And some of them were huge!” “They must have been!” Jody said, as she carefully and gently soaped me. “Here, Jen,” she said, “you do this.” Handing Jennifer the sponge, she motioned toward my tender pussy. “Put your fingers in her to make sure we have everything, but be careful! Poor baby! Can you imagine having so many men fuck you over and over and over?” she asked as Jennifer timidly washed my pussy hole. “I bet Elizabeth takes you there someday!” she said. Jennifer’s eyes rolled up and for a minute I thought she might faint; she regained her composure and shook her head vigorously, but her eyes betrayed a trace of real lust as she contemplated what would surely be her fate one day.
When I was bathed, dried, collared, belled, and dressed again in a pretty sissy party dress with lots of lace and ribbons, white stockings and pink high heels, the three of us walked back to the living room to find our three Mistresses chatting and laughing. At that moment, the doorbell rang, and Mistress Angela motioned for me to answer the door. I found our guest of honor, Diana, with her sissy slave slut Danni standing meekly behind her. Diana was tall, over six feet, and statuesque. Her bobbed black hair was thick and shiny, her makeup heavy but perfect. Her dress was clingy in all the right places, and she stood on 4 inch heels, adding to her already impressive appearance. “Slut,” she said by way of acknowledging me. She breezed past me dragging Danni on a black leash into the house. She greeted Mistresses Angela, Catherine and Elizabeth who warmly wished her a happy birthday with hugs all around. Diana had in fact been born male but had opted in her late 20s to become a kick-ass transsexual dominatrix, and she enjoyed a huge following of both men and women. Danni was her personal sissy slave, a confirmed gay man who really preferred the company of hairy, virile men. But Diana had captured Danni at one point after seducing him in a bar d***k and made him/her into something Danni wished-to-god she could change. She was always very uncomfortable around women, but here she was, transformed into a feminized sissy, controlled by a formidable tranny dominatrix, and at a party where no real men were anywhere in sight (or mind). She was dressed in a stunning little black cocktail dress, sleeveless, her longish blonde hair pulled back and tied at the nape of her neck with a black ribbon. The collar her leash was attached to was black patent leather, adorned with white pearls, and her shoes were strappy heels, definitely FMN (fuck me now) shoes if ever I saw them. Her breasts looked real enough, and they appeared to be disproportionately large for her slight frame. She was now a woman, all right, a lesbian’s dream girl. That was Diana’s intent, to transform Danni into something men lusted after but could never have, even though Danni would have given anything to be solely in the company of men.
As the party got underway, we sissies served our Mistresses drinks and light finger foods, hovering nearby to make sure their every whim was satisfied. After a number of drinks, the talk turned to sex, and Diana went on to describe how she had had Danni’s tits enlarged to a 36DD. She didn’t bother to chastise her. She knew that Danni would never get to be a man’s lust object again, and she was rarely aroused around women. Sissies presented a special treat – females with cocks, and Diana liked seeing Danni fucking and being fucked by obviously female-looking sissies. “I’ve been training her to lick pussy, too,” Diana said, “even though I know she hates it. Come here, slut! Show the girls what you can do.” Danni meekly walked across the room, eyes down, and knelt next to her Mistress. “Strip!” Diana commanded, and Danni quickly pulled her dress up over her head. She was naked underneath her dress, her huge tits hanging succulently against her slight body. Her little cock didn’t stir between her legs. “Who’s first?” Diana asked. “Me!” my Mistress replied, hiking up her skirt and beckoning to Danni who crawled obediently across the room to Mistress Angela. “Take her panties off with your teeth, bitch!” Diana ordered, and Danni obeyed, pulling Mistress Angela’s panties down to her ankles and then off over her feet. Slowly she crawled between Mistress Angela’s spread thighs and dutifully licked and sucked her cunt. “Remember your lessons, you little slut,” Diana cautioned. “Find her clit and give it the love it deserves.” As Danni licked and sucked and my Mistress moaned in obvious pleasure, the three of us sissies and the other Mistresses watched Danni’s perfectly smooth ass and heavy swaying tits with obvious envy. I noticed that her little cock stayed limp, and I also noticed that she had a jeweled butt plug peeking out between her ass cheeks. “Such a perfect little sissy girl, isn’t she?” Diana said with obvious pride. “And to think she hates being like this, and having to eat pussy! I never let her near my male clients, although sometimes I tie her up and gag her naked in the room when I’m having a session with a man. The clients love seeing a sexy tied up sissy with big tits, and what I’m doing to the men makes Danni’s cock swell right up. That’s even more of a turn-on for the client. But I never let her cum that way. And the only clients I let her ‘help’ me with are the women. She gets to do her pussy practice on some of them. What can I say? I’m a heartless bitch who loves irony!” Her laugh was almost evil sounding. When Danni had brought Mistress Angela to several glorious orgasms, Diana ordered her to do the same for both Catherine and Elizabeth, both of whom eagerly accepted the reluctant but voluptuous sissy’s oral attention.
While this was going on, our Mistresses encouraged the three of us sissies to begin pleasuring each other. Jennifer’s gag was removed but she was ordered not to say a word. When she undressed, we saw that her body had been shaved smooth, but she still had the look of a man dressed in women’s lingerie. Her wig added to the look of a feminized man in transition to full sissyhood, but she willingly opened her mouth and sucked on Jody’s little stiffy. Once she got Jody hard, it was her turn to lick my pussy and also tongue the tip of my clitty, licking up the drops of pre-cum that oozed from it, making the bell jingle as I tried in vain to get hard. While Jennifer mouthed my clitty, Jody fucked me from behind, marveling that my pussy still felt tight even after so much fucking the day before. Whenever Jennifer’s mouth wasn’t on me, my bell tinkled furiously as Jody pumped my ass and my caged little cock and jewels flopped up and down with each thrust. When Danni had finished off the women, Diana had her stand in front of the three of us while we took turns sucking her cock and playing with her gorgeous tits. We pulled the butt plug from her ass and, at Elizabeth’s suggestion, stuffed it into Jennifer’s mouth to lick clean. Danni found herself responding in spite of herself, and eventually sported a nice hard-on. At this point everyone took a turn sucking on her nicely erect cock, and the women laughed as it began to get limp again when each of the women took turns sucking her. It was only when someone with a cock sucked on Danni’s dick that it grew hard again. Diana thought this was hysterical and only proved what a twisted creation she had come up with. At last Danni was ordered to let Jennifer make her cum, and she closed her eyes as the feminine looking Jennifer sucked and licked her until her cum gushed onto Jennifer’s sissy face. “Leave it there,” Elizabeth ordered. Jennifer obeyed, occasionally licking her lips as the cum slowly dripped down her face to her mouth. Clearly she was going to make a wonderful sissy slut, with or without her balls.
“Bend over!” Diana ordered after Danni finished cumming on Jennifer’s face. Danni bent over the table, raising her ass for her Mistress. Diana raised her skirt, revealing a raging hard-on that went well with her large, imposing figure. She strode over the Danni and plunged right into her gaping pussy, fucking her hard and fast for the next few minutes. She reached around and crushed Danni’s swinging tits in her big hands as she pounded her from behind, pinching and pulling Danni’s nipples until she squealed with pleasure and pain. When Diana finally came in Danni’s ass with a loud groan and a last hard thrust, she stayed there for a couple of minutes, letting the rest of her cum spurt into Danni’s bowels. “Cream pie for dessert, sissies!” Mistress Angela announced after Diana withdrew and stepped back from Danni. “Lollipop first,” Diana said, pointing at her softening cock. “Jody, clean her up,” Catherine ordered and Jody rushed to kneel in front of the towering domme and eagerly sucked her cock clean until not a drop of cum or anal mucous remained. She licked her lips and looked up at Diana for approval. “Well done, little girl,” Diana said. “I may have to invite you to one of my parties in the future to do clean up on all my guests. Would you like that?” “Oh yes, Mistress!” Jody said eagerly, shooting a hopeful glance at Catherine. “I would love that Mistress Diana!”
“Gather round, girls,” Mistress Angela said to the three of us sissies still on our knees. She moved to Danni who was still sprawled across the table top, her legs spread, tits flattened against the shiny dark wood of the table. “Don’t you dare waste a drop,” Mistress Angela ordered. “I want to see a three-way snowball. Sharon, you first!” At that I knelt behind Danni’s beautiful firm ass and sealed my lips to her well-fucked asshole. I probed her with my tongue sucking slightly and was rewarded by the first drops of Diana’s cum oozing into my waiting mouth. I waited patiently, holding the warm cum in my mouth, and was happy to feel more of it dribbling from Danni’s hot fucked hole. I slurped it up, still holding it in my mouth, until I was sure I had collected most of Diana’s offering. I turned to Jennifer and kissed her on the lips opening my mouth to let the warm gooey cum run into Jennifer’s mouth. Jennifer then crawled over to Jody and kissed her, drizzling Diana’s load into Jody’s eager mouth. “Show us!” Mistress Angela commanded. “Show us the cum!” Jody crawled over to where the women were seated and went to each in turn, opening her mouth and showing the prodigious load of semen she held there. “Danni! Get your sissy ass over here and swallow your Mistress’ cum!” Diana ordered, and Danni quickly crawled to Jody and lay down on her back, mouth open. Jody knelt over Danni and let the cum dribble into Danni’s waiting mouth for what seemed like five minutes. “Wait til you have it all!” Diana said, and when Jody finally finished the transfer, Danni gulped and swallowed her owner’s huge load.
“Well, that was delightful!” Elizabeth said, “But if you will all indulge me, this is also kind of a coming out party for Jennifer, and I have one last little surprise for her.” Jennifer quickly glanced at her Mistress and then lowered her eyes submissively. “Come here, darling,” Elizabeth said seductively. As Jennifer crawled to her Mistress, Elizabeth reached into her bag and pulled out a harness and large strap-on. “Stand up and turn around, slut,” she said when Jennifer got to her. Jennifer obeyed, and Elizabeth buckled the harness around Jennifer’s waist and between her legs, positioning the strap-on just above Jennifer’s caged cock. “This is the only kind of fucking you’re going to be doing for at least the next six months, dear, and the only way you’re going to fuck me, possibly for the rest of your life, so I want to give you a little preview. Jody, come here, dear. I think you’re the only sissy who didn’t get her pussy stuffed this afternoon, except for Jennifer, but then she’s got a kind of permanent stuffing going on,” she said, referring to the steel ball residing in Jennifer’s ass-pussy. “Go ahead, Jennifer. I want you to fuck Jody’s pussy until she cums. Do you think you can do that for us?” Jennifer nodded and moved to position herself behind Jody who had raised her slim boyish ass and lowered her head to the floor, kneeling in front of Elizabeth. Jennifer eased the strap-on into Jody’s ass with a sigh, and Jody moaned softly at the invasion. For the next 10 minutes, the room was filled with the sound of Jody’s moans and sighs and the slapping of Jennifer’s pelvis against Jody’s pale ass cheeks. Jody’s little clit rose and stiffened, bobbing up and down with the rhythm of Jennifer’s fucking. “Sharon, help your sissy s****r out,” Mistress Angela said, and I lay down on my back, putting my head between Jody’s thighs directly under her bobbing cock. I guided her cock into my mouth and sucked on it lustily, enjoying the slim size of it as well as the knowledge that it belonged to one of my favorite girlfriends. Of course I would help her out. I would love to have her cum in my mouth. The tiny bell between my legs tinkled softly but constantly. As she got closer to cumming, Jody began panting “Thank you! Thank you! Thank you!” with each thrust of the strap-on dildo. Jennifer thrust harder and harder, and Jody’s little cock got harder and harder in my mouth. I felt it swell just a little more, and a big jet of hot cum hit the back of my throat. I loved it, loved taking her sweet juice into me, loved the taste of it, loved giving her pleasure. I sucked and sucked, rubbing my tits and playing with my own nipples as I drained her little balls. Jody squealed with ecstasy, her hips spasming as her orgasm continued, making it hard for me to keep her in my mouth, but I kept sucking until I felt her start to soften. I came back to reality to the sound of soft applause from the four Mistresses in the room. “I’m proud of you, Jennifer,” Elizabeth said. “I may never let you fuck anyone with your real cock again. You have a flair for the strap-on! Snip, snip!” she said, making a scissors gesture with her fingers. I could almost feel Jennifer cringe in response, and I felt kind of sorry for her, but then I know there are many, many sissy pleasures she could have even if her sissy clit remained locked up forever or she lost her little sack. She would learn to cum in other ways, as I had.
Sharon goes shopping for a date