Three Sissy Quickies free porn video

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THREE SISSY QUICKIES by Throne Marissa called out from the living room, "Poppy. We're waiting for you to bring the snacks." From the kitchen an intimidated voice answered, "But your friend... she's never seen me before. I mean, like this." "Well, it's about time Jen saw you. After all, she's my best girlfriend. We share everything. So get a move on." Paul picked up the 3-tiered tray and walked carefully on his 3 inch heels. He got almost to his destination and stopped. The women were chatting about some TV show they both liked. It was a crime drama and, because his wife deemed it too upsetting for him, he had never been allowed to watch it. As he stood there trying to gather his courage, he pictured the two females. His wife Marissa was short and busty, with a trim waist and well padded hips, along with a round jutting bottom and shapely legs. He appreciated that she was short, because so was he. And her curvaceous figure was a delight, except that nowadays all he got to do was look at it. She had declared that he got too excited about sex and so would have to be celibate for a while. When he asked how long that was, she told him it would be for an indefinite time. That had been three months ago, at the beginning of his sissy conversion. Instead of lessening his excitement, staying chaste had him thinking about sex 24/7. It didn't help that his wife appeared to go out of her way to be visually provocative. All that made it much easier for her to manipulate him. Jen was similarly short with generous curves. Seeing the two of them together could only increase his yearning for release. Worse, because his wife had him in Poppy mode, Jen would be seeing him for the first time as his sissy self. It was bad enough having his wife sneer at him, mock him with her gaze, and make sardonic remarks. But Jen had never liked him, certainly hadn't respected him, and had even disparaged him in front of his bride. He suspected that it was Marissa's friend who had given her the idea to control and feminize him. "Poppy!" It was Jen this time. "We're waiting." He tried to square his shoulders but lacked the confidence for even that slight display of self assertion. So he was demonstrating complete girly body language as he entered the room. Jen eyed him up and down for several seconds before she broke out laughing. To her hostess she said, "Oh, Marissa. This is priceless. Look at the pathetic wimp. You really did a number on him." "I did. Of course, with such a spineless guy it's easy. And you might recognize some of the stuff he's wearing. Remember all the clothing we bought at the thrift store?" "That junk? You said it was for Halloween costumes but I suspected something else. After all, we'd been talking about you doing this to the wuss for a while." "Yeah. And thanks for all your input. You had so many good ideas and you were you so enthused?" "Always happy to help. Right now I want to get a better look at his makeover." She reached into her handbag and pulled out a digital camera. "And some pictures." Paul could only stand there with the tray. He had his knees together and his elbows close to his sides. Jen took a few pictures and then stood up to walk around him, so she wouldn't miss anything. He was mortified to be seen in what he had on. His hair was only two inches long, but his wife had put product in it and combed it upward and tied a scarp around his forehead. The scarf had rainbow stripes and hung down in the back. His eyebrows had been thinned and his face was made up. Jen had used foundation and blush, eyebrow darkening gel, mascara, eye liner and shadow. Then she had applied lip liner, garish magenta lipstick, and a coat of gloss. He had a sleeveless top over his slender torso. It was bright pink and had the word 'CUTE' written across the front in looping red letters. It ended just above his navel. Below that were tiny cotton shorts, of vivid yellow. There were flesh colored stockings on his hairless legs and then those heels, which were red and had rhinestones on their tops. Jen snickered and trailed her fingertips over his exposed lower back. He quivered under her touch and sniffled. Stopping directly in front of him, she said, "Your own wife turned you into an absolute sissy. And in only three months. Twelve weeks. Though she did have a good start, you being such a weakling to begin with. Not at all like my husband Matt. Now he's a real man." She looked at Marissa. "Don't you think so, hon?" "I'd sure like to find out," she replied with a leering grin. "But right now my creampuff spouse has to serve us our snacks." Jen sat back down. Both women were wearing snug, low-cut tops that showed plenty of cleavage. And tight slacks that accentuated their nether curves. Paul was much too aware of their physical charms. His enforced celibacy tormented him. He took a steadying breath and went to Jen. Bending forward at the waist, as he had been taught to, he held out the treats to her. There were petit fours and miniature cupcakes and bon bons and more. Naturally, he wasn't allowed to eat anything like that. When his wife indulged in sweets he could only look on and salivate. That's what he had to do now, close enough to inhale the tempting aromas but not permitted to sample any of it. Jen sat there studying the selection. Because he had to maintain that unnatural posture, his back almost immediately began to feel uncomfortable. The guest had him rotate the tray slowly while she remained indecisive. He tried not to ogle the exposed tops of her plump breasts. At last she took one item and waved him away. He went to his wife who smirked up at him. She had Paul sink slowly into a deep squat and left him like that while she talked to Jen about a movie she was waiting for to be available on her pay cable service. Jen said that she had bought the DVD and would be happy to loan it to her. "After all," she said, "you and I share everything." Paul was trying to decide if there was some hidden meaning to that when his wife finally took something off the top tier and also shooed him away. He stood with his back to the wall, trying to be nonintrusive. The women gabbed about clothes and Marissa said Jen could try a new belt she had recently purchased. Paul remembered that one. It had been very expensive. His wife had made him look while she modeled it, along with other acquisitions. She even finished with a short nightie that had made his balls throb with unmet need. While they were still discussing clothes, Jen commented, "Poppy walks well in those heels. Was it hard for her to learn?" "It was at first. But I made her keep them on for an entire weekend. Once her feet and ankles recovered from that, she did rather well." To Paul she said, "Show her, Poppy. Put down your tray and swish around the room a few times." The he-she husband felt himself blush. He put the tray on an end table and began circling the room, adding extra hip action to his movements, holding his hands out to the sides with his wrists limp. It was demeaning but he would rather humiliate himself than risk his wife's anger. She could be endlessly cruel, as he had learned when she made him crouch in the half-filled clothes hamper, scrunch himself all the way down, and then closed the lid on him and set the bathroom scale on top. She had gone off to grind coffee beans, brew a pot, and unhurriedly sip a cup, while he was stuck in that cramped space, breathing the odor of unwashed clothes. Their conversation slowly ran down. He dared to hope that Jen might leave and this difficult encounter would end. Besides, he still had a half dozen pairs of Marissa's delicate panties to hand launder. That was especially time consuming because he was required to suck the crotch of each one until it was pre-cleaned. He was silently wishing for the visitor to leave when he was startled by a loud knock on the front door. Paul stood there, paralyzed by fear. Was another of his wife's girlfriends coming to be amused and entertained by his plight? Marissa said, "Poppy, be a good girl and go answer the door. Now." His hands were shaking and his knees threatened to buckle as he went to the door. It could be anybody. What if it was a police officer, there to tell them that Jen's car was parked wrong and had to be moved? He put his hand on the knob, turned it, held his breath and opened the door. There stood Jen's husband, Matt, with stubble on his square jaw and a crooked grin. He looked down at Paul and snorted derisively. "Mind if I come in, Paulette?" The smaller man stepped aside. He wrung his hands as Matt passed. Then Paul closed to door before someone passing outside might spy him. Matt went to his wife, who stood up to greet him. They embraced and shared a deep kiss. Then Matt went to the snack tray, took the biggest sweet he saw, and tossed it into his mouth. Marissa said, "Poppy was supposed to offer you the tray." Matt nodded. "She's not trying hard enough. Guess she'll have to be punished." "But later," Jen said. "Let's get to what we're here for." Paul was confused. What were they talking about? He just wanted Matt to go away. Having a woman beside his wife seeing him while he looked all sissy was terrible. That woman's husband eyeing him up and down was ten times worse. "So how are we going to work it?" Matt wanted to know. "I need Poppy at our place," said Jen. "Before I do anything else, she's going to give our bathroom a thorough cleaning. While I watch, and if she slacks off or misses any spots I'll be there to... motivate her." Marissa offered, "And I'm staying right here. Can't wait to get Matt into my big bed. It's been too long since it's been used for anything except Poppy eating my pussy, and for sleep." "So, fine," Jen agreed. "I'll be at home in our bed, with my own personal sex slave for the entire night. And for tomorrow morning." They all shared a laugh. Paul looked from one to the other. His wife went to the closet and got him a long coat that would cover his sissy garb for the short drive. "Wait," Paul said, still trying to understand. "You're giving me away, Jen?" "Not giving you away, airhead. I'm trading you for Matt. Both us girls get what we need in bed. I know I certainly could use a big cock like Jen's always bragging that Matt has." Jen joined in with, "And I want my pussy pampered by Poppy's busy tongue, which Marissa tells me is quite a treat. Nothing like a complete submissive who you don't have to do anything for in return." "You... you're swapping?" Paul said incredulously. "Sure," his wife affirmed. "DVDs. Fashions like that belt. You know how Jen and I are. We share everything." ********* Betty was in the grip of sexual tension. He had a male name, of course. But at the moment he was wearing nothing put panties and fishnet stockings. His undersized dick was stiff and it bobbed as he vigorously buffed another pair of his wife's tall leather boots. He had done two of them previously. Each one had a different type of heel. There were four inch spikes, a three inch stiletto with a one inch platform under the sole, and the current design, a three and a half inch block heel that he kept gripping with one hand while polishing with the other. His small dick was hard because he had an obsession with feminine footwear. A pair of flashy shoes, something classy but with ankle straps or extra pointy toes, or else outrageous hooker heels. All of those drove him to distraction. But his main and most powerful attraction was to boots. He whimpered just then because he had to touch them to get his job done, but was only allowed to have his hands on the cherished glossy surfaces. Betty longed to rub the sleek uppers against his nipples, to lap the lowers, suck the heels, and best of all to press his puny penis against the sweet spot, in front at ankle level, and hump against it until he lost control and spurted all over that beloved, seductively scented material. He was hunched over the current object of his attention, unconsciously rubbing that hand-filling heel with his thumb, sneaking his face closer to where his cloth was rapidly rubbing the dark surface, and huffing the intoxicating and distinctive scent of leather... leather... leather. A voice from behind him broke into his perverted reverie and said, "Snorting that magical smell, are you? Not concentrating on what you're doing? Maybe I should just keep you away from my shoe closet." He turned his head. Towering over him was his wife Velma, slim and angular, with cupcake breasts that had high-set nipples. She had on a tasteful blouse and smart slacks, along with a nice but not especially exciting pair of sling-backs. He gazed up at her fearfully. "I'm sorry dear. It's just that sometimes my mind drifts." "And I can see from the state of your sorry mini-dick where it drifted to. You just can't control your lust when you're around my shoes and boots." She made a sour face and shook her head disapprovingly. "I guess I'll simply have to do something about that." "I... you can't... I mean, please don't take away my privileges. I do keep everything organized. And clean. Remember when you wanted those oxblood boots? The ones with the studs around the tops?" He moaned at the memory. "And I knew that they were all the way in the back of the closet." "Yeah," she said with a sigh. "Because you put them there. So they'd always be handy for you to fetish when I was out anywhere." He smiled sheepishly and confessed, "Well, yes." "You are incorrigible. And I will have to make a change. But for right now I think I'll give you a treat. Find me my riding boots. The ones that fit so perfectly over my calves." Betty's breath shuddered. He reached for the boot rack in the closet, his hands going unhesitatingly to the second row from the bottom, and took the pair she desired. Velma sat on the edge of the bed and chuckled at her panty and stockings wearing spouse. He was helpless under the spell of boots. She made him gingerly remove her shoes and put them back into the shoebox where she currently kept them while awaiting delivery of an additional shoe rack. Then he gave her a brief foot rub. His erection didn't diminish. It still pressed outward against the panties' front. With a chuckle she granted him the honor of putting the riding boots on her. They fit snugly but with care he got them on, not encountering any problems. As he did it his arousal mounted. While he knelt before her, ravishing the boots with his eyes, she brought up her lower leg and teased his genitals with her foot. The touch of boot leather against his thinly encased privates made him gasp. She massaged his erogenous zone while he held onto the edge of the mattress and groaned, not knowing how far she would take this. "All right," she told him, sounding bored. "You can have sex with my boot. I'll even let you lower your panties. But don't take forever." "Th... thank you," he whispered gratefully as he yanked his panties down onto this thighs and inched forward on his knees. His hands went to the back of her heel and he elevated the lower portion of her leg just enough to give himself the ideal angle for what was to come. Betty got his pecker against the boot so that the underside of his organ was in full contact. Beginning slowly, he made kinky love to the mesmerizing riding boot. "That's it, Betty Boot," his wife said soothingly. "Get it on with my boot the way you're not allowed to with my body. Do it, you hopeless sissy. Show me what a freak you are for my boots. And how far you are from being a real man. You and your poor excuse for a cock. Demonstrate why I had to put you in panties and stockings and cut off all your rights to real sex. Hump that boot, sissy. Come on that lovely leather, Betty Boot." Her words pushed him over the edge much too soon. He grunted, squeezed his eyes shut, and spurted onto the gleaming leather. As soon as the last of the cream left his body, he slumped forward, still holding the heel of her riding boot. "Now lick it clean, girl," she ordered imperiously. "Make it quick." He bent to his unsavory task, his tongue moving rapidly, as he made himself swallow his own spunk. He gagged slightly but got it all down. The moment he raised his head she barked at him to go to the bathroom and clean his crotch at the sink. She also forbade him from rinsing his mouth. As Betty washed off his undersized male parts, he automatically checked to see if any hair was growing back. That was a habit he had acquired earlier on, when he was still using regular applications of depilatory to keep himself smooth down there, as well as everywhere else. Now he had to remind himself that those self-inspections were no longer necessary. His wife had gotten him laser treatments and none of the eliminated hair would grow back. Ever. As soon as he was cleaned and dried, he rushed back to see what else she wanted. Maybe his wife was in the mood for him to serve her orally. He preferred to do that before he was allowed to finish, on the rare occasions when that happened, but right now he was so glad she had let him spend intimate time with one of his favorite pairs of boots, that he didn't mind. He got there but she wasn't on the bed. He could tell that she was palming something in her hand. "Sit where I was," she told him imperiously. "And spread your legs." She opened her hand and held it out. What she had been concealing was a chastity device. A cage that would contain his penis and prevent erections. He had seen plenty of those on-line and knew that this was as small as they came. His wife assumed the position that he had formerly taken and worked the chastity over his flaccid member. She worked efficiently, snapping the holding ring around his scrotum, behind his testicles. Then she fitted the two pieces together, took a little heart-shaped lock, and slid it through the connecting openings. "Go ahead, Betty," she told him calmly. "Close the lock. Make it impossible for you to get hard. Now and until I decide otherwise. I'm tired of worrying that you'll mess with my shoes and boots when I'm not here. So from now until whenever, I'm keeping you locked. Do it." There were two sounds. The lock clicked shut. Betty Boot sobbed. His life would still include being made girly. And being the keeper of his wife Velma's collection of shoes and boots. But now that footwear would torment him because he had no way to release the passions it triggered. Without being told to, he bowed his head and kissed the area where he had just been permitted to hump her boot and spurt on it. That would likely be the last time in a long while he was able to do that. For a long while and maybe forever. ********* Charlie was stuffed into a pink, satiny party dress that was designed to be worn by a little girl, but had been specially made in an adult size. Whenever he was home his wife Edna kept him in similar fashions. He also had on pink tights and matching ballet slippers. There was a blond wig perched on his head, with sausage curls hanging down on the sides and back. In front it had bangs. His face was decorated with extra long false eyelashes, too much rouge on his cheeks, and dark pink lipstick that was applied to give him a bee-stung mouth. He hated being made to look this way but it was what his wife had done to him after he was caught cheating with his secretary. He either had to surrender to her complete control or face a devastating divorce and one-sided settlement, charges of sexual harassment and worse, the loss of his job and becoming unemployable. There was even a good chance he would do jail time. He knew what could happen to a guy like him, short and with a slight build, blond and soft featured, if he was on the inside. The secretary had sex with him willingly, but made sure she had all sorts of evidence that suggested otherwise, and then blackmailed him. When she got bored with that she let him have her once more but arranged for several of the other women to catch them, including the female boss. And made sure it looked completely non-consensual. So now he was stuck in this insulting role. It had gone on for half a year and he was gradually succumbing to it. He was prone to pout or break down and cry. Sometimes he was petulant and would even stamp his foot or, on one occasion, stick out his tongue. Charlie fought to hold onto his grown up male persona. When he was at the office, where they had allowed him to stay on but with less authority, he sometimes found himself acting immature. It didn't help that he always had cotton panties on under his trousers. And part of the agreement to not fire him included depositing his pay directly into an account that was in his wife's name alone. It was all so difficult. But lately he had been telling himself that he would prevail. And find some way to turn everything around. He would begin working on that this evening. Edna was going out to one of her female friend's homes for a wine party. She expected to sample several different bottles and therefore planned to sleep over. Charlie would have until the next day to think his way through all this. Sitting on a white, ice cream parlor chair that his bride had bought especially for him, he tried to organize his thoughts. She had given him an oversize lollipop that he was expected to eat... like a good little girl. Charlie stuck out his lower lip and frowned at the candy. His wife was suddenly there, saying, "If you keep looking so grumpy, your face might freeze like that. Would you want to always look so sour... Cherry?" "No," he responded, crossing his legs at the ankles, shoving the candy into his mouth, and giving it several hard sucks. "I'm glad to hear that. You know what happens when you show a bad attitude." Then, as if he didn't know the answer, she told him, "You get spanked. Is that what you want?" He took the lollipop out of his mouth, licked his lips, and forced a half a smile onto his face. "No, Mommy Edna." She was a full-figured woman and lately had appeared somewhat matronly in his eyes. At the moment she had on a dark skirt suit and her hair was up in a tight bun. His eyes went to her very full bust and he tried to remember when he had been able to put his hands on it. And to have sex with her. Those memories were sometimes difficult to access. She granted him a tolerant smile. "And don't forget that the reason I call you a pretty name like Cherry is to remind you to have a good attitude. Cheery Cherry." He nodded and popped the pop back between his lips. Why couldn't she just leave? He had so much to think about. These days any distraction made it impossible to concentrate. He attempted to focus but lost his train of thought when he heard a car pulling up out front. "That'll be your babysitter, Cherry. I wouldn't want to leave you all alone, girly." "My...? I don't need..." He was too flustered to properly make his case. Edna went to the door and opened it. In walked Maria -- his secretary. The dark-haired, dark-eyed beauty smiled at him. She had a large plaid zipper bag with its long straps over her shoulder. Charlie couldn't help recalling all the sex they had shared. "I don't understand," he managed to say. "Well, you need an adult to keep an eye on you, Cherry. And Maria seemed like a perfect choice." "But she's the one who seduced me." "I'd hardly call it that," his wife corrected. "You went after her. I mean, she threw a few hints your way, but that was only because I asked her to." "What?" "Well, I'd had a conversation with some of the girls. The ones I'll be seeing this evening. It was about cheating husbands. I told them I was absolutely certain you would never do that to me. It turned into a bet. I'd met Maria at your company's office parties, and we'd hit it off. So I requested that she flirt with you a tiny bit, never imagining you'd take the bait. When you did, I was infuriated. She thought it would be fun to let you have some sex with her -- she's very easygoing about that sort of thing -- and then stick it to you with blackmail. I was more than happy to go along with it. It was amusing to watch you get calls from her, and see you go into a nervous dither. Then we staged that final act that got you into so much trouble. After she agreed with your employers to make a few changes to your status, I had part of what I wanted. But it wasn't enough and, with the leverage I had, turning you into a harmless little girl struck me as the rest of the payback I needed. Making you over into someone who could never even think of cheating on me or any woman again." Maria added, "Clever. Right? Don't you agree... Cherry?" She tittered. As she set her capacious bag on the sofa, he felt weak in his knees. The situation he thought couldn't get any worse had just done exactly that. And with Maria there he wouldn't be able to even start planning to save himself. It was all too much. He held the long stick of the lollipop in both hands and lapped at it furiously. His secretary said to his wife, "You should go now, Edna. I'm sure we'll be fine together, me and your sugar-sweet girl. I'll just make sure everything I need is in her diaper bag." Charlie choked out the words, "Diaper bag?" "That's right," Maria told him. "Remember that, even though your lovely wife is getting her revenge on a nightly basis, and 24/7 on the weekends, you still owe me. After all, I had to put up with your selfish performances in bed. The way you slobbered all over my tits -- UGH. So I decided to make you a baby whenever I feel like it." She grinned at him. "Unless you want to do something about it. I mean, the company left the matter of your sexual misconduct open for the next five years. If I tell them that I'm suffering post-incident trauma, you could still end up behind bars. Would you rather play baby with me or be a cellblock bitch for a bunch of sweaty men?" "I... I'll cooperate." "Great. But when you talk to me, don't sound like Charlie, the way you just did when you got upset. Or even like young Cherry, like Edna tells me you have to here at home. No, I want to hear baby Cherry. Can you do that for babysitter Maria? Or how about Aunt Maria?" He went blank for several seconds before saying, in a feminine, babytalk way, "Okay, Miss Maria. Cherry be good." "That's more like it. And don't break character while I'm feeding you your bottles or changing your diapers." He almost blurted out some words of protest at that last revelation. But self defense prevailed and he clapped his hands lightly together, grinning foolishly and babbling, "Bottles. Diapers. Auntie Maria. Yay!" Edna, looking more maternal than ever to her husband, gave him a sly smile. She was obviously enjoying this. Maria whispered to Charlie that he should be sitting on the floor. She unzipped the bag and laid out a large cloth diaper and baby powder and lotion. He shuddered at the prospect of what was going to happen soon. Next she took half a dozen filled bottles from an inner cooler section of the bag and put them in the fridge. Then she took his lollipop, telling him that he'd had enough candy. But she promised to spoon feed him lots and lots of healthy mush. A sense of powerlessness overwhelmed Charlie. Or as he was more and more thinking of himself, Cherry. Maria put a bonnet on top of his wig and tied it under his chin. She pulled mittens without thumbs over his hands and fastened them securely around his wrists. He realized that his fingers were now encased in thick padding and rendered useless. Finally she took a fat pacifier and draped its ribbon around his neck. Charlie's wife smirked at him and then left for her overnight visit. Maria tickled him under the chin. Her touch had a mildly erotic effect but he felt more like a toddler than a man. "We're going to have so much fun," Maria assured him. "And I'll come to visit you as often as I can. Now let's get you out of your tights and into a nice warm diaper, with rubber panties over it, before you start drinking all those bottles. Okay, Cherry?" He could only tell her, "Okie, Maria." She was already spreading a blanket on the floor next to him. It was covered with cartoon animals in bright colors. Charlie gave up and let her turn him and ease him back until he was lying there, looking up at his former bed partner, her shapely breasts under a colorful T-shirt with no bra holding them. Her sweet face smiling down at him. She pulled up his dress and worked down his tights, removed his footwear, and got the tights the rest of the way off. From the bag she also took a pair of ankle socks. Maria told him, "We're going to have such a good time, Cherry. All night and into tomorrow." ********* (For any readers who want to read stories with primarily gay content, I now have some on the free fiction site, gayspiralstories.com. Their specialty is mind control themes. If you take a look at my efforts and want to comment, please leave a review there. Thanks.)

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THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

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...

1 year 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...

2 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,...

3 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...

1 year 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...

1 year 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...

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...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

1 year ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

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