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Chubby Sissy Hubby by Throne It was a black lace, stretch teddy, with wired cups. Or rather they were half-cups. I looked at it lying on the bed and thought I would start crying. Did my wife Tyra honestly expect me to squeeze into that? When I heard her approaching our bedroom a chill of dread filled me. She came into the room and put a hand on my shoulder. All I was wearing was a short diaphanous robe with a string tie at the waist. I clutched its front and pulled the halves together. She chuckled in my ear. "What's the matter, Leslie? Don't you like what I picked out for you to show off in? Afraid it'll show off your weight gain? Don't you think it's appropriate for the occasion? Are you afraid my visitors won't like it?" "P... please," I said miserably. "I can't have your lady friends see me in that... that..." "That sexy seductive bit of nothing?" she offered. "I've already told them that I found out about your naughty hobby and that I'm just helping you to become the sissy you've always longed to be." "But that's not... I don't really want to..." "No-no, now." She waved away my concerns. Tyra is so desirable. Tall and full-figured, with a full thrusting bust, flaring hips, a jutting round bottom, fleshy thighs, and large firm calves. That was what had drawn me to her from the beginning. She had on a sports bra and yoga pants. Smiling down at me from her superior height, she said, "The alternative is to tell them that I've had to turn you into my mincing girly-boy against your will, and reveal some of our bedroom secrets. Would you rather have them find out how weak willed and confused you are, and how much you've forced me to take over your life? I'll do whichever you prefer." "It's just that... I never thought..." "I know. It's the same as you keep telling me. All you want is to occasionally put on panties and prance around when I'm not home. But now that I know that Lester sometimes turns into Leslie, I'm taking you further. Helping you to fulfill your dreams." "I was happy just... you know... doing what you said." "You only thought you were happy. Once I get you past this silly display of reluctance, I know you'll really blossom. You have to accept my assistance, Leslie. And I can give the girls either version of your story. What should I say to them?" My lips quivered. Tyra just couldn't be convinced she was pushing me past my limits. And she thought the reason I didn't want her friends to see me was because I hadn't admitted my real feelings to myself. The real reason was that I was happy being Lester almost all the time and only needed to indulge my desire for panties and stockings now and then. Having them see me would be utterly mortifying. But I could never get her to change her thinking. And now those women were due to arrive in less than an hour. I surrendered and said, in my faint Leslie voice, "Yes, dear. You can tell them I want all this." I nearly choked on those words. She likes me to show appreciation so I added, "Thank you for your support." "No problem," she assured me. "Now let me help you into that gorgeous lingerie." She untied the filmy robe and slipped it off my shoulders. I stood there, naked, very aware of the absence of any body hair. When my wife had gotten me treatments so I would be smooth all over, I assumed the effect would be temporary. Since then I'd learned, to my horror, that it was permanent. She ran her fingertips appreciatively over my soft hairless chest. "I think you've gained another pound or two. That diet is giving you the girly curves you crave." "Yes, dear," I told her even thought I wasn't happy about it. Months ago, repeatedly saying she knew I'd be happier with feminine contours, she had started me on a high calorie and fat-heavy eating regimen. I had piled on the pounds rapidly, until now my formerly trim shape was gone, replaced by a plump chin, chubby arms, a protruding belly, wobbly thighs, and a fat rear end. Worst of all, I was developing man boobs. She liked to joke about how, with my weight gain and hairless state, all pink and squishy, I resembled a big baby. She took the teddy and got down on one knee, holding up the lightweight garment for me to step into. I got both feet through the openings and she worked it up my overweight legs. Tyra snugged it into place. She tucked my smaller-than-average genitals down and back, where they were easily held in place. Then she tugged the teddy up so I could get my arms through it. Finally she zipped it up in back. When she came around front again she eyed my chest critically. After a few adjustments of the top she was satisfied. "It's everything I'd hoped for," she self-congratulated. "Those half- cups hold up your boobies and show them off perfectly." She gave my nipples a playful double tweak. "You must be ecstatic. Or will be when you see yourself in the mirror." She patted my bottom, encouraging me to go to the full length mirror mounted by the closet. Sure enough, not only was my doughy figure shown off unflatteringly, but those unwanted male breasts were put onto display, pink and given the size of oranges by how they were lifted. I shuddered inwardly at the unmanly sight I made. "Now," she said, "let's pretty up your face and fix your hair, Leslie." There was nothing I could say except, "Yes, dear." As I moved to the vanity table my chest mounds rippled, much to my shame. If only she would take me off that awful diet. I sat my pillow-bottom on the round chair and looked at myself in the mirror. I'd never had much of a beard but now there was none. My eyebrows were thinned out slightly. It wasn't enough to make people gape at me when I was out but I always got second glances. And I think some of the people at the office where I work were wondering about me. Tyra applied foundation and went to work with cosmetics. I had to see my face being changed from passably masculine to undeniably feminine. I wrung my hands and tried not to let my emotions show. She doesn't make me grow my hair long but there's enough for her to back-brush with gel in it and achieve a girly effect. With my soft features and the beginning of a double chin I resembled a chubby young lady. The make-up was overdone just enough to guarantee I would feel extra shame when her friends got an eyeful of me. My wife had me stand and mince around. She decided I needed stockings and selected a pair of fishnets with elastic tops. Then there were black heels, which thankfully were only two inches. Finally she let me pick my own jewelry. The catch was that if I didn't choose something on the flashy side she would say I was in denial about my true tastes and give me substitutions anyway. So I selected large plastic hoop earrings, matching bracelets, and a ring with an oversized plastic 'gem' on it. The earrings were screw-on ones because she hasn't had my ears pieced -- yet. Also, I think she almost seems to enjoy tightening them more than is comfortable. I had to do some more walking around, adding extra sway to my hips, and then she declared me ready to meet my new public. The women were due to arrive soon. I paced around nervously. Tyra said I needed to eat something to settle my nerves but that it could wait until her guests arrived. All too soon the doorbell rang. At least she didn't make me answer it. Instead, I had to hide in the dining room while she welcomed her friends and took them to the living room. I tried to adjust my top to somehow make it present my chest less dramatically but that was impossible. After all, that was what the teddy had been designed to do. And the sheer panel in front was taut over my expanding belly. Not only that, but the rear was merely a thong, which left my unmanly buttocks exposed. After the women had chatted for a few minutes my wife called, "Leslie, dear. Come in here and meet everybody." I shuddered at the prospect of being gawked at. Still, there was no way to avoid it. I left the dining room and went to where they were waiting. All conversation stopped as I walked in. All eyes were on me. There were three women. They must have been from Tyra's BBW support group, as they had the same zaftig figure as my wife. My humiliation was mixed with lust at seeing that trio of plus-size beauties. "Ladies," my wife said, motioning toward me. "This is Leslie. She used to be my husband Lester but once I found out how much she wanted to look and act like a female, I spared no effort to make it happen. She's getting to live her dream." Then she introduced me to the others. They were Annie, Barb and Zell. Annie said to me, "I can see you're succeeding at being all girly. I want to get that teddy in my size. Come over here, honey, so I can get a closer look at all your pink softness." She had dark red lipstick, which to me suggested a wanton sexual appetite. I went to her reluctantly. She made me stand directly in front of her, put my hands on my hips, and bend forward at the waist. That put my bust within easy reach. She asked Tyra, "Are her nipples sensitive? Is it okay if I test them?" "They're more receptive than mine," my wife assured her. "And I'm sure she'd love to have you play with them. She's such a slut." Annie reached up to capture the ends of my boobs between her forefingers and thumbs. She rolled them gently, sending waves of stimulation through me. I moaned in spite of myself and couldn't keep from wriggling my hips. Annie chuckled and said, "You really get off on this. Don't you?" If I didn't want my wife to reveal how she controlled my life and that I was too weak-willed to fight back, I had to go along with the fiction that I wanted all this. At that moment I didn't want the shame Annie was causing but I also didn't want the pleasure she was giving me to stop. "Yes," I told her in my high soft voice. "It feels so good. Please keep doing it." She laughed and took away her hands. "Maybe we can play some more later. But I can't monopolize you, sweetie. The others all want a turn, I'm sure." "Me next," called Barb. She had dark bangs, which is a look I find irresistible. "Come over here and sit by me." She patted a spot next to her on the sofa. As I lowered myself to sit she slipped her hand under me, unnoticed. I yelped in surprise and all the women laughed. Barb made no effort to remove her hand. Instead she felt my wide cushiony bottom. I knew better than to try to escape. As accustomed as I was to anticipating Tyra's wants and trying to satisfy them, I instinctively rose up just enough that Barb could explore my entire backside. She pawed and kneaded it, in no hurry to be done. I whimpered from upset but realized the sound could be mistaken for desire. The auburn-haired woman gave me a parting pinch and told me give Zell a chance. The last female wore glasses with large frames that drew attention to her emerald eyes. The eyewear had a studious or businesslike appearance, which contrasted with her lush figure and the way she licked her lips at my approach. Zell said, "You're so smooth all over. How do you manage that?" "I... had the hair removed..." As much as I didn't want to share the rest of it, I didn't want to irritate Tyra by slipping out of character. "I had it done permanently. It makes me feel so femme. I'm so happy that none of that awful man-hair will ever grow back," I lied. "So you're totally committed to becoming as girly as you can." It was time for an even bigger untruth. "Absolutely. That's why I put myself on a weight-gain diet. I want tits and a big butt." "Well, you've made a successful start. Tyra told us about your calorie quest, so the three of us got together and decided to each bring you a fattening treat, as a surprise." She looked over at my spouse. "You don't mind, do you, dear?" "Not at all. The last thing I want to do is interfere with Leslie while she's on her yellow brick road to happiness. My job is just to help her on her journey." Zell smiled at me and opened her capacious shoulder bag. From it she took a box of six cream-filled Wing Dings. "Here you go, sweet cheeks. Gobble them all down." I looked toward my wife, hoping she would allow me to eat one and save the rest, but she just grinned maliciously. I opened the box, unwrapped the first one, and stuffed the end into my mouth. As I chewed and swallowed, Annie was producing something from her own bag. It was a package of cheese sticks, which I realized immediately wouldn't combine well with what I was already eating. She motioned me nearer and got one ready for me. As soon as I had forced down an entire Wing Ding, I started on the cheese stick, a fried concoction of dairy product, grease, salt and added fat. By the time I was halfway through that, Barb was already summoning me to her. What she had brought was a quart of cheap pineapple-flavored soda, which turned out to be warm and flat. I opened it and took a long swallow. At least it would wash down the food. My stomach was already protesting from the uneasy mix of choices. And there was so much more for me to consume. "So," Zell asked my wife, "is Leslie any good for sex? I mean, being a sissy and stuffing his face all the time?" "Well, he's no good for regular sex. But food isn't the only thing he overeats. I got him started using his mouth on my pussy and that's been a big success." To me she said, "Hasn't it, blubber butt?" I nodded. Had she really just revealed that? And I was too deep into backing her up to share the truth about how I felt. Around a mouthful of food I managed to say, "That's right. My wife makes me... do that... and doesn't let me have... intercourse." That wasn't a lie. But I desperately wanted to tell the rest of the story. I took a glug of soda to clear my mouth and instead told them, "Tyra is totally supportive of everything I'm trying to accomplish." Barb wanted to know, "Is your sissy husband that good at playing the pink harmonica?" "Like you wouldn't believe." Annie joined in with, "And he likes doing it?" "Loves it. Can't get enough of having her face between my thighs." "So..." Annie said thoughtfully, "if there was another woman for him to use his skills on, that would be a good thing for him." "Oh," Tyra said with sudden understanding. "Are you volunteering to help Leslie?" "Well, if your pantywaist honestly wants it..." Everyone's attention went to me. My cheeks were bulging with food. I decided that if I tried to retreat from this awful situation, my wife would simply find some way to get me stuck in it again. If I protested that none of this was what I wanted, she would probably tell them that was a big part of my fantasy, to be an unwilling participant. In my mind's ear I could hear her saying just that, and making them believe it. So I tried to appear enthused and nodded vigorously. Barb offered, "I'd take some of that too." Zell made it unanimous with, "I'm in too. But I guess we'd have to figure out when to do it and all." "You know," Tyra decided out loud, "I'd hate to have you all make separate trips back here without knowing if his technique was to your tastes. I mean, I'm sure he'll approve of how YOU all taste." They laughed at that. "But why should I have you each make a special trip before you even know if his style works for you? How about if we just let you three give his face a test ride now?" This couldn't be happening. I was still gorging on that unwanted food, which was overfilling my stomach and making me queasy. Because Barb had let the soda lose its carbonation, I didn't even have the consolation of it producing burps. It took an effort for me not to moan from the growing discomfort. To me it looked as if my tummy was bulging, though that might have just been my imagination at work. The visitors watched me with renewed interest, now that they were expecting intimate contact and lots of pleasure. I tried not to let my upset show. At long last I was down to the last Wing Ding and final cheese stick, along with the dregs of that unappetizing soft drink. OMG, talk about overeating. I was extra aware of my recent weight increase, especially my fat bottom and those shameful man boobs, so well advertised by my black lace, stretch teddy, which was getting plenty of stretching. Tyra snapped her fingers at me. "Ups-a-daisy, lovely Leslie. On your feet. That's a good girl. Now give those bubbies a shake for all your new friends to see. Your soon-to-be-very-special-friends." I rose unsteadily to my feet and gave my chest a halfhearted up-and-down jogging, which made my insides feel even worse. The women watched me avidly. Annie wanted to know, "Who gets to use the sissy first?" "You're the one who so helpfully thought of it, so move to the front of the line." Her mouth, with that dark red lipstick, curved up in a devilish grin. As she got up, the others' attention flicked back and forth between her and me. All three women were stunning, with their generously padded figures. Under different circumstances seeing them could have been such a positive experience. But at that moment, in the depths of my humiliation, wearing that teddy and with my face made up, having to maintain the illusion that this was what I craved, and having been made to gorge on junk food, it was quite the opposite. The thought of using my mouth on three pussies made me more nauseated than ever. Annie took my hand and towed me along behind her. Tyra called out, "The guest bedroom is at the end of the hall, on the right. Please turn down the duvet. Don't worry about getting wet spots on the bottom sheet. I'll have Leslie do a load of laundry later on. She adores housework. It makes her feel so wifely." At that point Annie dragged me into the spare bedroom. I dutifully adjusted the duvet and even fluffed up both pillows, though she would be using only one of them. After she sat on the edge of the mattress I got down on my knees in front of her. She had on low boots, which I carefully removed, mildly excited just to be handling her footwear. Then she laid back and spread her legs. I got alongside her and she raised her wide bottom so I could tug down the tight slacks she wore. Her lower half was gloriously attractive, all well formed contours. I hooked my fingers under the waistband of her lacy French-cut panties. She didn't make much of an effort to help me. Annie lifted her hips only slightly and didn't keep her legs close enough together. The result was that I had to work harder to get them off her and, more importantly, had to touch her more. Soon my little penis was straining against the crotch of my teddy. She noticed, pointed, and giggled. "That looks like a prick, only smaller. Way smaller. But I guess for a sissy like you, it's an asset. Makes you feel less like a man. Am I right?" "Yes, Ma'am." It was strange to be aroused and sick to my stomach at the same time. Kind of like I was being punished for feeling pleasure. I got into the position I was so familiar with from Tyra, on my knees and head down, mouth very close to the juncture of her legs. Normally I would have had my hands on Tyra's hips but I wasn't sure what Annie would allow. As if reading my thoughts she said, "Go on, Leslie. Steal a free grope." When I touched her that way my palms tingled. Annie's feminine scent was no stronger than my wife's but slightly different. Her labia were thicker and rippled. My tongue popped out automatically and I got my first taste. As I began to lap her she sighed. Her legs moved further apart. I got my lips firmly against her split mound and kept my tongue moving. Then I alternated that with sucking on her clitoris. She reacted as if she'd never had that done to her before and thought it was the best thing ever. I continued switching back and forth to prolong her enjoyment, but eventually I could tell that she was accelerating toward an orgasm and would not want to be taken off that direct course. So I got two fingers into her and used my mouth exclusively on her button of love. That did the trick and she was launched into a soaring climax, complete with jerking her legs in unison as she peaked. I lapped her through a slow descent and then she let out a long sign. "Damn, Leslie, you may be a dud when it comes to screwing, but you eat it like a champ. I'm going to get as much of that as I can." She got herself together and walked unsteadily out of the room. As she left she hollered, "NEXT!" Moments later Barb appeared. She eyed me from under her dark bangs, then said, "Let's get down to it." After she was on her back atop the bed, long pleated skirt spread out, she told me, "Get under there and take off my panties. Go on, Leslie." I did it, registering strange sensations while my head and shoulders were inside her skirt. I gingerly eased her panties down and set them aside. "Okay?" "Perfect. Now get back in there and make me get as noisy as Annie was." After I wriggled under her skirt she gathered some of it up so she could fling the hem over my back. I was in the dark, the warmth and her musky odor confined in that close space. I found my target by touch, using my lips and tongue. Then I fastened onto it like a suckerfish. I probed the interior and swirled around the entrance. She murmured appreciatively and pressed her heavy thighs against the sides of my head, making my sense of being trapped even stronger. Simultaneously, my stomach sent signals that it was still overtaxed. My mind was having trouble separating the joy of being with a voluptuous woman and the gastric distress from my forced feeding. I mouthed Barb through two quaking climaxes before she relaxed and let me out from under her voluminous skirt. I was still trying to recover when she got up, patted me patronizingly on the head, and went out. As I was attempting to get my thoughts straight, in walked Zell. She eyed me lasciviously thorugh those large-frame eyeglasses. She unfastened and whipped off her wraparound skirt. Despite everything that had happened, I was mesmerized by her heavy but shapely legs. Her panties were soon off. She motioned for me to come to her and then pointed toward the floor. I understood and put myself in front of the tall commanding woman before getting down on my knees. She said, "How about a kiss?" I was eye-level with her neatly trimmed pubic hair but as I leaned forward she pivoted and presented me with her wide, well-upholstered rump. I was in no condition to fight back. My full stomach continued to rebel as I pressed my lips to one cheek and then the other, over and over. Then she made me wedge my face between those yielding hemispheres and finish with several very intimate kisses, delivered over several minutes, each one lingering much too long. When she turned back the other way and planted her feet well apart, I was relieved to be lavishing my attentions of a wet pussy again. I held onto her thighs and lapped hard, getting my tongue into her cleft each time. She shivered and purred and held onto my hair. Zell got wetter than any of the others and gave my lower face a good pussy washing. I coaxed her into a violent orgasm that made her practically gush. She pulled my head down and rubbed herself as dry as she could on my hair. Putting her skirt back on, she pinched my ear, hauled me upright, and walked me out to where the others were waiting, panties in her hand. I had to kneel in the middle of the room, like some exhibit, while they discussed me. "Such a devoted pussy licker." "Really rocked my world." "Kisses ass like a sissy slut." "And you're all welcome to keep on sharing Leslie," my wife promised them. "I was thinking we could all get together this time next week and have a sort of theme party. Each of us could find a sex toy for my sissy. It could be something to provide pleasure or to give pain." "Ohhhh," Annie said. "I've seen those chastity thingies online. Would that count as pleasure or pain?" "Get one and we'll let the sissy decide." "How about stuff to, you know, restrain him with?" "Bondage gear? Always welcome." "Or it could be things that weren't meant to be used for kinky games, but we can repurpose them. Like a dog collar and leash." "How about diapers?" "And fresh produce. Like a big fat cucumber to go you-know-where." I could barely follow everything I was hearing. They went on endlessly, laughing and throwing ideas back and forth. All of that, along with the taste and scent of women so strong in my mouth and nose, interacted with my upset tummy to keep my libido off balance. It was almost as if I was coming to equate indigestion with sexual excitement. And there was the weight I was gaining, and how that was changing my bottom. How much bigger would those chest-warmers grow? "And the week after that," Zell enthused, "we can each bring something special for Leslie to wear. Help to build his pansy wardrobe." "This could go for weeks." "Months." "Years." "And we'd be getting so many orgasms from that talented sissy mouth the entire time." I couldn't believe how bizarre my life had become... and how much more like that it was now guaranteed to get. ********* (I've recently read several stories by Lisa Lovelace and enjoyed them all. You might want to check out her THE NEW ADMIN.)

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A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Chubby Freshman Chapter 13

James softly kissed the cute chubby freshman not wanting to frighten him away by rushing things. As the senior student kissed Jerome he put his hand to the freshman’s smooth boyish cheek and caressed softly. Jerome seemed to respond to the kiss and opened his mouth and the experienced student gently pushed his tongue into the boy’s mouth. As the kiss seemed to finish and without a word both excited students holding wine glasses nearly full slowly moved to place the wine glasses on the coffee...

1 year ago
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Chubby Loving

Are you a Chubby Loving kind of masturbator, or do you prefer a more traditional set of beauty standards when you’re picking out the pornstars you’d most like to see fucked? Well, if you fall into the latter category, perhaps you’d better go check out one of my other lists of smut here at ThePornDude because the BBW stuff isn’t for you. But, on the other hand, if you do like a lot of extra meat on your sandwiches and your sluts, I think you’re going to love what you find here.Unlike the...

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2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

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