The Sissy Challenge free porn video

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The Sissy Challenge by Cassandra Morgan Even in her human form, the panther glided across the floor, an air of danger about her. Her almond eyes pierced the night, separating prey from peer. A growl emerged from her throat, low and menacing. Her handler tugged at her leash, and she slunk into the crowd, her shoulder muscles rippling gently. She passed a woman in handcuffs, and a very large baby in a stroller. There was a weightlifter in a collar, walking behind a woman in leather. There was a woman with a full beard walking behind a man in super-hero garb. Good lord, did Dane love Fetish Night at B.J.'s. Oh, he was a fairly recent visitor here. Dane and his wife Bella, and their friends Oliver and Annie, had started coming in about a month ago to check out the human zoo. There was every kind here. Gay men and astronauts. Animals and knights. Babies and cavemen. Girls in football uniforms and men in wedding dresses. They were the vanillas. Oh, they tried to pass as a pair of the more adventurous couples, but they knew better. They were sight-seers. They were oglers. Some of the regulars looked down on them because of that, but others just shrugged. Everyone had started by looking into the asylum through a window. Everyone was drawn originally by curiosity. And so they looked. At the pain freaks. At the sadists. At the Littles, who cradled their teddy bears. At the Furries. At the masochists. At those who dealt pain. At those who absorbed it. At the babies. At the Satanists. There were so many ways the human mind worked, so many things that got people through the night. If you can think of a kink, someone was into it. Rubber. Leather. Insects. Ponies. Urine. Feces. Whatever. Blowjobs. Toejobs. Nose jobs. Clown sex. Dirty Sanchezes. Blumpkins. Donkey punches. A dog in a bathtub. A tuna melt. A dutch oven. A Bismarck. Every twist imaginable had been imagined. Everything you could think of to do had been done. All of it. The four of them, Oliver and Dane, Bella and Annie, had talked about it long into the evening. Theoretically they were for anything by consenting adults that didn't cause long-term damage. Gay? Big deal. Transsexualism? So what? Bondage? Old news. But, yeah, they were human, and they got a chuckle out of seeing a fat man in a tutu or an old woman in a diaper. There was a difference between being offended and being amused. But, honestly, every color in the rainbow is a good one. So they sat there, nursing beer - always overpriced at a fetish club - and chattering away, when a familiar figure appeared at the table. It was Suzanne, the waiter/waitress. Suzanne was a very large man in a very little girl's dress. Think of a linebacker dressed like Alice in Wonderland. "Get you guys anything else?" he growled. "Suzanne, I love your shoes," Annie said. "How did you find them in your size?" She smiled, and lifted one of them toward Annie so she should see better. "You can get anything," she said. "Even Mary Janes in 13 ?." Bella leaned in for a closer look. "They are so sweet!" she said. "And they go perfectly with your dress." "Thank you," Suzanne beamed. "I got them for the contest." "What contest?" Oliver asked. "The Hunger Games?" "No, silly," Suzanne said ."Our annual contest at the bar, The Sissy Challenge. Are you guys going to enter?" "No," Oliver said. "Maybe," Bella said. "Tell us about it," Annie said. And so Suzanne did. Every year, he told us, there were several contests at B.J.s. Any reason to celebrate, you know. In this case, they invited sissies to enter for prizes and awards. You got to pick how far you delved into the lifestyle. You could simply carry a feather duster, and you'd be allowed to be in the contest (although you would get booed off the stage). You could do the full Cinderella package. Annie was laughing out loud by the time he was finished. Bella was about to cry. Yeah, Oliver said. It sounded funny. All these mincing sissies flitting across the stage, the ones who took to it naturally and the ones who did not. It wasn't about dressing like a sissy, not totally. It was about being submissive to your partner, to letting the lifestyle envelope you. "God, Oliver. You'd be great!" Bellow howled. "You're small. You're pretty. Hell, you obviously own a maids dress! You'd be perfect." "Stop," he said. "How about Dane?" Annie said. "Dane has great flipping legs. He's a little tall for a sissy. But he has these pouty lips. Get him a set of tits, and he'd be fine. Curtsey for me, Dane." "Very funny," Dane said. "But it's, um, kinky that you think I could be girly." "Hold on," Annie said. "I like it. I'd get to be the Mistress! I've always wanted to be a Mistress. Now, go get me a drink!" Dane frowned. Oliver folded his arms. This was silly. "Come on," Bella said. "At least lets talk about it. What's the problem? You wear a dress? Big whoop. You wear lipstick? So what?" "And you do the ironing!" Annie laughed. "I'd like that! I'd love to have my very own sub." "God. Wake up and the coffee's done! Breakfast in bed! No more dishes to wash!," Bella said. It went on that way for a while, the women cackling, trying on the idea of their husbands waiting on them hand and foot, and both hand and foot wearing fingernail polish. "Think about it like this," Bella said. "There is nothing that says nail polish has to be worn by women. Or perfume." "Or skirts," Annie said. "That's all by society's insistence. The plumbing doesn't demand which gender wears panties. Bras, yes, because women have boobs. But you could have long hair as well as me. You could wear lipstick." Their arguing got more united, more pointed. Dane and Oliver kept trying to argue back, but they were losing. No surprise there, Annie said. Women were better at arguing. They were sharper, more clever. "I want this," Bella finally said. "I think it will be fun. I think it will be an adventure." "Hell, it's what...six weeks?" Annie said. "You can play dress-up for six weeks. Think of it as Halloween. Think of it as a Roleplay party. Just relax and go with it. It'll be a blast." Then they were making plans, about how many panties to buy, about how many dresses we needed. Should we sleep in nightgowns? Should we wear bras all the time? How about lipstick? Eye lashes? Hose? Before long, the conversation had gotten away from the men. They looked at each other. Dane rolled his eyes. Oliver shook his head. The women were a runaway train, and each idea stacked on top of the previous one. They were intent, designing beauty, and nothing else mattered. They were the puppet-masters, and the strings were being attacked to Oliver and Dane. Oliver looked out on the floor. Two women were dancing. One of them was wearing a gray suit. The other a green dress. He was one of them now, he thought. He wasn't a bystander any longer. * * * That night, Dane called Oliver on the phone. They had things to discuss. "How are you doing, Oliver?" "I'm okay. A little nervous." "No need. Look, they could be dressing us up like Batman and Robin okay? It's just roleplay stuff. No big deal." "Yeah, but dresses? Lingerie?" "Ah, no sweat. I say we go with the flow. So we wash dishes for a few weeks. So we wear bras. What's the big whoop. You've seen the things people wear at B.J.'s. It's a six-week costume party. Nothing more." "I guess..." "Hell, it's going to be easier for you." "Easier? How so?" "Well, no offense, but you're girlier than I am. You'll be able to pass. I'm a bigger lug. I'm going to be obvious. Hell, I've seen you in the shower at the club. You won't even leave a bulge." "Hey!" "Ha. Sorry, bro. " "Hey, Dane?" "Yeah." "Are you ... looking forward to this?" "Forward? Not really. I'm just going to endure it. I'm going to have a good attitude. I'm a six for six weeks. How about you?" "You won't make fun of me?" "Um...no." "I've had a hard on all night. I'm kind of looking forward to it. Don't tell." Dane stared at the phone. His best friend was a fag? Don't tell, his ass. He couldn't wait to tell. "Don't worry, Oliver," he said. And he bit his lip to keep from laughing. * * * That night, Annie climbed into bed next to Oliver and looked at him. She handed him a pair of panties. "How are you do, sweet cheeks?" she said. He looked down. "Please don't call me that." "Aww," she said. "Is my sissy upset?" "I'm not a sissy." "Oh, come on, Oliver. Remember that schoolgirl outfit you wore for Halloween? You were Brittney Spears in that video. So cute." "You wanted me to wear..." "Oh, stop it, Oliver." She looked him in the eye. "Look, this started as a discussion, but I have to tell you. I want it. I think it's going to be great fun to turn you, to control you. I want to be your Mistress. It excites me. My nipples get erect when I think about it. You know, I've always kind of called the shots for us. When we bought our Honda, I picked it out. When we rented our apartment, I picked it out." "But a sissy?" She looked at him and sighed. "Oliver, you knew I was bisexual when you married me. No one knows that but you. But I fell in love with Oliver. You. Your gender didn't matter to me then, and it shouldn't matter to you now. I miss breasts. I miss the smell of perfume, the feel of lingerie rubbing against mine. I miss lipstick on my crotch sweetheart. Remember when I had you dress as a Supreme for Halloween. It was the same as this. I miss my Olivia. I want her back." He looked into her eyes. There was love there, and something else. There was a streak of control there, an insistence that things be done her way. It has always been there, he guessed. It was one of the things that attracted him to her. He took the panties. "Put them on, baby," she whispered. "That'll be a nice start." * * * Across town, Bella was watching Dane pull a dress over his head. "A little short, baby," she said. "You think so?" Dane posed in the mirror. "Yeah, I guess it is. Needs tits, too." Bella walked around him, checking him out like a fashion critic. It didn't particularly bother her that her husband was in a dress. It didn't seem to bother him, either. He was true to his word. He was treating this like a Halloween party. Bella bit her lip. He had no idea of what was coming. She could not wait to smack that bubble butt of his. This wouldn't be play all the way. But Bella had her secrets, too. She was fascinated by the world of domination. She read every article she could get on it, and when Dane wasn't home, she masturbated furiously to images of all her little sissies in handcuffs. No, she didn't particular find him sexy in a dress. He was too tall, too gangly. But she did like the idea that she could make him wear whatever the fuck she told him to wear, and he would bow his head and accept it. She liked that she could make him kiss her feet or cook her food. It's funny. In their marriage, she had been the giver. She quit her job to move with him to Cincinnati. She was prepared to have his children, back before they found out he was infertile. She cooked most of the meals. That was going to change. She was in charge now. Soon, he would find that out. * * * The next day, the four of them walked through the mall, the women in front, the guys tagging along sheepishly behind them. It was as if they had adopted the lifestyle already, and were meekly following their Mistresses from store to store. Annie held a bra up to Oliver's chest. She wrinkled her nose. Then tried another one. "Can I help you, ma'am?" the salesclerk said. "I'm Henry. Are you having any luck with sizes?" "Well, I"m buying lingerie for my husband. He needs some panties, some pretty ones." "He..." Oliver looked at the floor, blushing furiously. Did she have to tell the clerk? Did she have to tell the world? "Well, my husband is a sissy! Do you get many of those?" The man looked at me. He exhaled. "From time to time, ma'am, we run into his 'kind.' It's a new world, isn't it? Homosexuals are all over." "I'm not..." "Shush, dear," Annie said. "My good man, I'm prepared to spend money on bras and panties, maybe a corset. Can we use a fitting room? "They can share," Bella said. "We don't want to impose." Oliver blushed. He looked at the floor. Dane just looked at the sales clerk with a crooked grin. "We're fags," Dane said. "Want to come back into the dressing room with us?" The sales clerk muttered something about being busy. He rushed away as Dane laughed. "I'm telling you, Oliver, you have to have fun with it. The girls are hell-bent on this, evidently. So treat it like it was a giggle. Sissies for six weeks. That's us." Oliver picked up a pair of the panties. "They're ... girly," he said. "Do they have to be so lacy?" "Oh, my sissy princess will love it," Annie said. "You may never want to go back to boxers. You know, a lot of men who aren't cross dressers wear women's underwear. It's so much nicer." They all squeezed into the changing room. Oliver didn't know the wives were coming with them. But there they were, and clearly, Bella expected to see Oliver naked and Annie expected to see Dane. Annie fussed with Oliver's bra, lifting the cups out, frowning. "I wish we had one of those magical bracelets from the stories, the ones that make your tits grow," she said. "Or a chemical cream. Or a breast pump." "Yeah, what are you going to do?" Bella said. "I mean it. What are we going to do." "I don't know. She needs boobs, though. I guess breast forms. We'd never get hormones to work in six weeks." "How about implants?" Annie pinched his nipple. She lifted it. "I don't know," she said. "Would the soreness be gone?" "Mine would be," Bella said, laughing. "Annie, I don't want..." "Did I ask?" she said, coldly. "I'm sorry." "I mean this is a big decision. Don't worry your pretty head about it, ok. We'll get you titties some how or another." Dane was posing in the mirror on the other side of the changing room, his left profile and then his right. He pursed his lips. He flipped his wrist at the mirror. He seemed to be taking this much better than Oliver. Bella was cooing and clapping as he tried on one article of clothing after another. Annie pulled a wig onto Oliver's head. Dane's hair was borderline length for a sissy, but Oliver's was short. A wig was a must for him. She had picked a blonde one. "You okay in there, ma'am?" It was Henry, the sales clerk, damn him. The snoop, trying to steal a glimpse. "Well, they're a little baggy. Can you come in here and check them?" She opened the door, and Oliver wanted a hole in the world to swallow him up. He stood there in lavender panties. Annie had a bra in her hands. "See what I mean. They don't quite fit right." "Well, these are what we granny panties Why don't you try to the new bikini cuts? Your...sissy... will like them, I bet. And some breast forms. That bra will need some breast forms." "Well, I had thought about implants, to tell you the truth. But we might as well start with forms. You're going to need something, aren't you Olivia?" "Olivia?" Dane said. "I like that. Olivia." Oliver stared at him. "You'll get a girl's name, too," he seethed. "Just wait." "We do need to talk about that, sweetie," Bella said. "I was thinking of keeping it simple. Dana? Do you feel like a Dana?" "Um, sure." "Might I make a suggestion, ma'am," Henry the salesclerk said. "Of course you may." The women turned to him. "Do you want the best in sissy-wear? The absolute best. We have a black maid's dress that is to die for. All the little girlie-boys love them. Might I fetch one for you?" Annie looked at Bella and grinned. "I think that sound perfect, Henry," she said. Henry disappeared. Oliver looked at Annie. "Do you have to tell the salesman?" he asked. "It's bad enough that you treat me like a sissy. But it's embarrassing for another guy to see me like this." "That's the point, Olivia," Annie said. "You're supposed to be embarrassed. You're such a simpering little girly boy. I find it quite titillating, to be honest. And judging from your little winkie in your panties, you do, too." Oliver covered his penis with his hand. Dane laughed. "You do have a little winkie!" he said. "If you got a sex change, they'd probably only charge you half price. You have a sissy dick! No wonder this suits you." Oliver bit his lip. Then there was a noise, and Henry was back. He had three maid's dresses draped over his shoulder, of assorted sizes. Oliver hated this. A woman's dress can be classy or cute or elegant, but a maid's dress screams servitude. You are ... the help. People glance at you and know you scrub toilets. You are less than human. He stepped into the dress and pulled it up. Annie zipped him ... her up, then ran her hands along her sides. She smiled. Her husband felt womanly. She took the breast forms Henry had brought and inserted them into his bra. "Oh, look at my hot sissy," she said. "Don't you think you look delicious? You're so beautiful. Ins't she beautiful Dana? You'd fuck her, right?" Dana looked at Olivia. "Well, she looks damn good. I'll say that. If you fix her makeup, she's going to make a lot of guys hard. Um, assuming that's what she wants." Olivia looked in the mirror and almost died. He really did look feminine. Annie pulled his shoulders back, which of course make his boobs stand out more. She ran her hands over his erection. "Olivia likes this, don't you girl?" He couldn't get the word out. Finally, it crept out, a weak admission for the court. "Yes," he said. And he did. * * * They arrived home just before noon, their arms filled with packages. The girls had bought their husbands four dresses each, matching ones so they could be in uniform. They had bought out the makeup counter. Oliver's ears hurt from being pierced. "Well," Annie said. "We're just in time for lunch. Do you supposed you could whip something up, Olivia? Maybe a salad and half a sandwich? Isn't that what sissies do?' "Yes, be quick, or I'll get my belt," Bella said, grinning "Ooh, Mistress," Dana said. Bella looked at Dana. She was joking, but she had no idea how close to the truth she was. Bella had every intention of striping her sissy's ass before the sun went down. "Now, rush," Bella said. "After lunch, we'll pick out a dress for you to wear, and we'll get down to it. It's Sissy Day! You two are going to have so much fun." "Of course we are, too. But who's counting?" Annie said. "Wait," Bella said. "You don't just walk. You don't just plod like a farmer going to the fields. You saunter. You sashay. You mince." "More wrist," Annie said. "More hips," Bella said. And so, for five minutes, the men worked on sissifying their walks. There is a way of rolling the hips, of letting the wrists flop, that fits the personality. It sounded silly, as if they were doing some strange pantomime of a woman, but a slight exaggeration helped. Once they got into heels, Annie said, it would look good on them. And so they made lunch. With two of them it was no problem. Dana made the sandwiches, and poured the ice tea. It felt good to Olivia to have Dana there, comforting to be going through this with someone else. No, Dana hadn't bought in to the degree Olivia had, but she was still a sissy. Olivia looked at Dana's legs. They were long, nice. She looked up at her ass. Stop that, she told herself. Put those thoughts out of your head. Dana, meanwhile, was struggling with her chores. She had considered the clothing, and she had resigned herself to being part of a dress-up session. But working as a maid? Was that right? While Bella sat on her ass? It felt subserviant. Like this was real. The food prepared, they walked it out of the kitchen. No, Annie said. Sissies ate in the kitchen. Not with the Goddesses. No offense, she said. But people should stick with their own kind. After lunch, the sissies were rushed into the bathroom to use hair removal cream, and to shave each other where the hair clumped. They did that, standing there nude and close to each other. Dana's hands were on Olivia's shoulder, and to Olivia, it felt nice. Soothing, somehow. The whole world had turned on her, but at least she had one friend left. Hair gone, Dana broke out a dark crimson fingernail polish. He dabbed it on Olivia's fingers, then on her toes. She ran her hand up Olivia's legs and looked into her face. Then she grabbed a crimson lipstick and started to apply it to Olivia. She was leaning close, and her crotch pressed against Olivia's legs. Something caught in her throat. She looked at Dana, then closed her eyes and Dana leaned into her. The two kissed softly, briefly, their lips sparkling with electricity as they touched. "You two die in there?" Bella shouted. Olivia opened her eyes. Dana smiled at her. She kissed her quickly again, then parted. "Here we go," she said. She walked into the bedroom, where the girls had laid out their clothing. Dana picked up a bra, looked at it. She looked at Bella, who nodded sternly. And so the sissies dressed. The panties felt like God was touching their private parts. The bra was just tight enough to remind them that they had been sissified. The hose were wonderful cocoons of pleasure. The dress, the red one, was tight and soft and flowing. The petticoats felt over the top, but it was impossible not to flirt when wearing them. The heels were awkward, neither Dana nor Olivia were used to anything like them. The choker was dainty. The earnings were punctuation. They were studs; it was too soon after the piercings to wear danglers. Bella bunched Dana's hair and tried to make something of it. Finally, she just spiked it. But Olivia was wearing a wig. Annie pulled the hair apart, coming up with twin pig-tails. She thought pig-tails were sexy on a maid. That afternoon was spent walking, and practicing with eye makeup. The chores would wait a day. This was the coming out of a sissy, the shaping and posing. There were voice lessons. There was curtsying. "Olivia, I'm not going to make you call me Mistress," Annie said. "But when you speak my name, I want a reverence there. I want to hear "Mistress" even if you don't say it. From your tone. Got it." Olivia nodded. "Fuck that," Bella said. "I want to be called Mistress. I am your owner. If you fail to call me Mistress, I will spank you. If you fail to curtsy, I will spank you. If you do not do your chores sufficiently, I will spank you. I am your Cleopatra. I am your Evita." Dana had a questioning look, but said nothing. Suddenly, though, he didn't seem as cool about this sub silly stuff as he had the night before. *** It was late at B.J.'s, but it was still early. Bar time always lagged behind real time. The fetishists were just starting to come out, the blood drinkers and the devil worshipers and the ass spankers. Annie and Bella sat at a table in the corner. Olivia and Dana sat on the floor by their feet. No one thought twice about them, or about the fact that the men were dresses, women's clothing this time. After all, the Sissy Challenge was going on. A man into animal play floated by. He blinked. An owl, maybe, Olivia thought. Maybe a hawk? Suddenly, a large shadow appeared over the table. A familiar one. "I love it!" Suzanne cried. He stood there, a large figure in his little Navy dress. "You look fantastic, girlfriend." He looked at Olivia. "You can have any guy in the place. Just grab a swinging dick and hold on like Tarzan." Olivia blushed. "Um, I'm not into guys." "No, but they're going to be into you," Suzanne cackled. "And your big girlfriend here. Some guy is going to want to go up on her, I'll tell you. What great fucking legs. That ass is going to get so stretched out we may have to put a highway sign on it." Dana looked down. It was sad, really. He had been so confident, so full of swagger. Had he been beaten? Or was he merely waiting for the right moment? A lifeguard type walked by. He looked at Olivia. Smiled. Then kept walking. Annie noticed. "Well, well, Olivia. Looks like you may have a gentleman friend. I hope I put rubbers in your purse." "Lots of rubbers," Bella said. Two women walked by holding hands. Annie stared. Bella looked at her and smiled, then covered her hand with her own. Annie looked at Bella. Bella squeezed Annie's hand, then continue to hold it. Annie smiled, then interlocked her fingers into Bella's. Olivia noticed the moment. Yes, she had always known than her wife walked on both sides of the street. That had been true in college, and Olivia supposed it was still a part of her. Olivia felt a twinge of jealously. Licking Annie was supposed to be Olivia's job; had she lost that, too? She felt a hand grab her own. She looked down, and it was Dana. Dana had a lost look in her eyes, as if things were spinning out of her control. She needed a friend. Olivia mimicked her wife and laced her fingers through Dana's. Dana slowly lifted her hand and placed it gently on her crotch. Olivia felt his penis there. It was larger than her own, but probably no more than average. She looked at Annie, but Annie was kissing Bella. Her hand was on Bella's breast. It was beautiful, Olivia thought. God. Were they just two gay couples out on the town? It felt that way. His wife was necking with another woman. His fingers were on another man's penis. And they were in a public place. Olivia could feel eyes on her, and suddenly, it didn't matter what those couples were into. They could see her shame. She moved her hand. She looked to the dance floor. Susanne was dancing with a cowboy. Suddenly, Olivia was quite aware of herself. She felt her dress hem on her thighs. She felt the stickiness of her lipstick. She felt her pigtails bounce around her head. She looked at Annie, whose head was lolling back. Bella's hand was up her skirt, churning furiously. "Come with me to the ladies, kitten?" Dana asked. "Uh, no thanks. I don't need to go." "You need to go," Dana said. "Because I need to cum." Ooooh. Olivia stood, smoothed her dress. She followed Dana for a few steps. Dana reached her hand back and took hers. Together, they minced to the restrooms. They picked the door in the middle,the one that said "Sissies." Then they where inside, and Dana was kissing her, and his cock was hardening against her leg. Olivia felt her tongue invade her mouth, and then it was gone. Dana pushed down on her shoulders, and she sank to her knees. Dana pulled up the hem of her dress, and her dick popped out. And then it was inside Olivia's mouth, hard and intrusive, not nearly as soft as she had imagined. He was grinding, face-fucking her, urgently, desperately. Another man passed them, but they did not look up. They kept having their public bathroom sex until Dana twitched, then spurted. The load hit Olivia in the back of her throat, and she coughed. She swallowed what she could, then ran her tongue through his public hair to lick up the excess. Had Olivia always been a cocksucker? she wondered. It had taken her only a few days to get Dana between her lips. She had not been raped or coerced. She was ripe and ready. She kissed the head of Dana's flaccid dick. She looked up at her, and she crouched and kissed him again. "They were having fun," Dana said. "I thought we should, too." "Dana...are we gay?" "Well, you might be," he laughed. "No, sugar. We aren't gay. We performed a gay act. But I won't go to bed tonight thinking of dicks and men's asses. As long as you were in a dress, and you looked pretty, I thought I might as well get a blow job. Hell, if you hadn't just drained me I might fuck your ass, too." Olivia ran the tap, then leaned down and rinsed her mouth. She re-applied her makeup and checked to see if her wig was still straight. She turned and began to walk out. "Olivia?" Dana said. "Would you like to fuck mine?" * * * Not many customers know this, but there are private offices in the back of B.J.'s. You go past the restrooms, past the kitchen, and there they are. Suzanne had seen the intensity with which Annie and Bella were going at it. He saw their sissies slip away. So he had had gone over, taken Bella by the hand, who had taken Annie, and led them to an office. He pushed them inside, smiled and then closed the door, giving them their privacy. It was perfect. Bella had pinched Annie's nipple between her thumb and forefinger. She had bit her on the shoulder. And she pushed her down toward the floor. Annie admitted to bisexuality, but this was greater than that. This was a hunger, a yearning, that she could not resist. She wanted Bella, wanted her like a drug addict wants a fix. She sank to her knees, then licked upward on her thighs. Bella's hand dropped on Annie's head, then gently guided her face toward her. It was wonderful. The taste and the feel and the smell. At the moment, Annie didn't care if she ever had to make Olivia's little dick happy again. She was at the altar of almighty pussy, and it was good. Bella ground her face in hard, until Annie could barely dart her her tongue in and out. Bella wished she had handcuffs to restrain her. Maybe a paddle to spank her. Annie was a domme? Hah. She was the fucking domme around here. The fucking sissies were wimps, and Annie was pliable. She was in control, as it should be. Bella pulled her up, kissed her. She probed her ass with two fingers, three. She looked into Annie's face and saw the passion, that slightly unfocused look of servitude. She kissed her again, then reached up and slapped her across the face. Blood trickled at the corner of her face. She put her own hand to her mouth, then looked at Bella questioningly. "It's going to be like that, bitch." Bella said quietly. "You can domme that fucking Olivia sissy all you want. But I domme you. You will be my personal sissy. You will lick wherever I tell you to lick, and you tell the world that you are mine." Annie was flabbergasted. She'd thought of herself and Bella as the same rank, but obviously, that wasn't right. She was being claimed. She was being bitched. She fell to her knees again. She kissed Bella's shoes. "My ass," Bella said. "I want you to kiss my ass." And, as the ultimate surrender, Annie did. * * * He liked the pain. Spank him, slap him, whip him. Dana loved it all. It had started with Mistress Bella and her belt. It had graduated to cutting, to burning, to raping. When Dana was a guy, he was a happy guy. But as a girl, he craved pain. The sissy shit? He did it because Mistress wanted it. The gay sex? That was humiliating enough. But she told him the reason he was alive was to take what she could dish out. Mistress thought she was so tough. But Dana was tougher. She was the toughest sissy in the world. Tougher than blood. Olivia was different. This sissy stuff was made for her. Put her in a room with 100 cocks, and she would sit on every one. The pink faggot. He loved her and her innocence. But he wasn't like her.When Dana was a kid, he had read a story about a man imprisoned in an iron mask. That was him, only with silk panties. He laughed. He raised his arms and checked out his clothes. He rubbed his nipples through his bra. Olivia liked being pretty. It didn't matter as much to him. Oh, he liked when Olivia sucked his cock. What was not to like? He liked the intimacy. And pain. He liked the pain *** The dynamics had changed for the foursome. It was a caste system. Bella was at the top, and then Annie. The sissies were at the bottom, although it seemed that even there, Dana had the edge over Olivia. So many genitals to kiss, so little time. Bella had planned to have Dana sleep in a large dog cage she had purchased at Pet World, but by the time the group got to Annie's apartment, everyone was exhausted. Bella took Annie into the master bedroom where she kept her vibrator. She planned on a probing experience. The sissies, meanwhile, collapsed into the spare bad. They had early chores, so they needed sleep. Olivia spooned behind Dana, snuggling close before drifting off to sleep. Dana was awaked two hours later by Olivia's fingertips, which trailed lightly over her stomach and then downward. They lifted her dick, stroking it gently. As it grew in Olivia's hand, she gripped the shaft, then squeezed, then unsqueezed. Dana rolled onto her back to give her sister freer access. Olivia responded by kissing her nipples, then down her stomach. Then nibbled at the head of her cock, then took it into her mouth. She slid her lips down the shaft. Okay, maybe this was gay, Olivia said to herself. She no longer cared. She was a sissy, sudden and proud. She sucked the dick in deep, drenching it in her saliva. Dana's dick was a perfect fit in her mouth, she thought. This was no six-week contest. This was one moment in her whole life. There would never be a time she would not want to suck this cock. There would never be a time she would not want to wear a dress. She still loved her wife, but she was falling in love with Dana, too. It sounded so wrong, but it felt so right. Dana came, gently and not particularly profusely this time. Hell, she was drained. Dana fell asleep softly, peacefully. Olivia touched her beautiful face gently, running her fingers along her cheek. She kissed her softly. Goodnight, my love. * * * Bella was in a foul mood the next morning. Her sissies had overslept, and her breakfast had been late. Dana had not slept in her cage. And while she had fucked Annie with her strap on, she had not ridden her the way she needed to be ridden. What the fuck kind of Mistress was she? She cuffed Dana in the closet and closed the door. She spanked Annie with her belt. She bought a cock cage she had purchased for Dana and made Olivia wear it. She was Atilla. She was Genghis Kahn. In the days to come, Bella would demonstrate her mean streak over and again. She sent pictures of olivia to Olivia's boss, and Olivia had to tell him that she was transitioning toward a sex change. She took Dana to lunch at his golf club, dressed as a sissy. She found out where Olivia's parents were having dinner, and she took Annie there as a lesbian date, making out at a nearby table. All three began to fear her dark moods. She caned them all. She made Dana sleep in her dog cage. She performed golden showers with Annie. She took Olivia to a fly-by-night doctor and had him give her implants. Yet, things ran fairly smoothly with that chain of command. People accepted their roles, by and large. One day, for instance, Annie was walking through the house and saw Olivia going about polishing the furniture in the living. She leaded against the doorway and smiled. Her husband, at least what used to be her husband, seemed happy. She minced about the room - there is no better word for it - singing and dancing. It was like watching Cinderella whistling while she worked. "You seem happy, my sissy," Annie said. Olivia beamed. "I am, Mistress," she said. "It's a wonderful day, and the contest is coming up, and my chest feels better. Soon, I won't need a wig. What could be better?" Annie shrugged. "Some sissies would long for the old days." Olivia wrinkled her nose. "Things weren't that good then, were they , Mistress? You missed sleeping with girls, and I was wearing boy clothes. Mistress Bella wasn't complete. And Dana? She wasn't nearly as lovely as she is these days." "You don't mind that we don't sleep together anymore?" Olivia frowned. "I miss being your husband, because I love you," she finally said. "But I wasn't much of a man. I know that. It was like you wanted a guy, but at the same time, you wanted a girl. So you picked me. On my best days, I guess I was about halfway between the two." Annie looked out the window. "Bella can get me going," she said. "She isn't really a lesbian, I don't think. I think she's ... a controller. She gives up pussy so she rule. That's okay. I love her. Of course, I still love you, kewpie doll." Olivia smiled. "Thank you, Mistress. Have you had your lunch?" "I have. I got a salad when I was out. But thank you. You really are the best sissy in the world, no matter what anyone says." Olivia stopped. She looked at Annie. "I think it suits me," she said. "A girl thinks a lot when she's doing the dishes, or the laundry. I turned over so quick that I think all I needed was a nudge. I really didn't fight very hard to stay out of dresses or, well, out of bed with Dana. Do you think I was destined for this life?" Annie shrugged. "Who knows anything about destiny. An artist can be quite happy living as a house-painter. I believe in relationships. I believe in family. And the four of us are one big, strange family." Olivia looked at her. "Do you like being a switch? Going from being submissive to Mistress Bella to being a Mistress with Dana and me? Isn't it confusing?" "Not really. Everything seems as if it's reached its' proper level. I can butt fuck Dana in the morning and spend the afternoon being spanked by Mistress. It feels like one person, one personalty, you know? It's like eating steak and lobster. Both tastes blend together well." "Some of us like sausage," Olivia said, giggling. "Faggot," Annie teased. "Guilty," Olivia said. And they tittered together, one and a half sissies, one and a half subs. Life was good. * * * On the night of the Classic, B.J.'s was packed. There were gay cops. There were transgender Superheros. There was an entire herd of human ponies. There were Masters and Dommes, subs and adult babies. And, of course, there were sissies. Maybe a hundred of them, some in shimmering pink dresses, some carrying teddy bears, some holding the hands of fellow sissies. Dana looked through the crowd and saw Suzanne in a Madeline costume. She waved. She walked past a construction worker and did a double take, checking out the beefcake. "Man," Dana said to herself. "I'd like to get spanked by that." The night was set up very much like a beauty contest. There would a Maid's Dress Competition (instead of evening gowns). There would be a bathing suit competition. There would be a talent competition. There would be an interview session (bawdy and brash, to elicit a chuckle from the crowd). There would be singing in the fifth stage. Olivia thought she did okay in the Dress competition. She was small and cute. And her new boobs helped her with the swimming suit competition. She didn't know about the talent competition. She tried to do a tap dance in heels, but she wasn't flawless. She did okay in the interview session, but not as well as Dana, who kept making reference about how long he could blow the interviewer, who played along to the delight of the crowd. For her song, she did "Girls Just Wanna Have Fun," and her female voice held true. She did have fun. She looked out on the crowd, there were hundreds of spectators, all seeing her as a sissy. And why not? That was the way she saw herself these days. Yeah, she could joke about Mistress Bella's firm hand, but if Mistress Bella hadn't been there, if Mistress Annie hadn't been there, she would still be a sissy. She would still get up early and cook, and she would still clean, and she would still wear panties and a bra. She would still fold laundry and iron and tidy the common rooms. And, Dana or not, she would still suck cock. God, she loved cock. She looked out on the crowd, and she imagined this man as a partner, that man as a top, this man sticking through the glory hole of her imagination. No, Olivia didn't win. She finished sixth, which wasn't bad for a first- timer in a field where were there were so many sissies who had been in the life for years. Dana didn't make it out of the first round. And, surprise of surprise, Annie finished 23rd, not bad for a switch. Still, as a top 10 finisher, Olivia got roses, and the crowd cheered for her. It warmed her. She looked down, and even Mistress Bella was clapping. Next year, she thought. Next year, I'll win it. She had time. (c) 2015 Cassandra Morgan

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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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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...

2 years 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,...

2 years 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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