Miss Sheila DeVille's School For Wayward Boys free porn video

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This is a story involving explicitly described sex. If you think you might be offended by it, or you aren't allowed by the laws of the place in which you live to read such a story, don't. If you read past this warning, any offense you take or laws you break are your problem. I've warned you. Permission is hereby given to archive this story anywhere on the Internet, so long as I'm credited as the author, it is reproduced in its entirety (including this disclaimer!) and no fee is charged to access it. On the matter of fees: I wrote this story (and others) for free, and I never expected to get anything out of it except the occasional response or critique, either good or bad. Constructive criticism is welcome, though please don't be abusive, and remember that this is primarily an attempt at a wank-story, not something aimed at a Pulitzer Prize. My point being: the only benefit I get from writing is feedback, and it seems to be tapering off in recent years. If you like it, tell me! If you don't, tell me why! Leave feedback on Fictionmania (that's best), or send email to: [email protected] Put "your stories" in the subject line, or I might miss it in all the junk email I get. Miss Sheila DeVille's School for Wayward Boys By Ed Miller Miss Payne walked down the hallway of Miss Sheila DeVille's School for Wayward Boys, on her way to her fourth period class. Her swaying ass, her huge, bra-less breasts, and the way she thrust her shoulders back proclaimed her confidence, her enjoyment of her position and her day. The boys she passed in the hallway saw what looked like an assured young teacher, barely into her twenties, with a body, a face, and a long mane of golden hair that assured her a starring role in their adolescent fantasies. There was nothing to suggest that anything else had ever been the case. The halls she walked through presented a slightly more unusual sight. At most public high schools, a teacher of Miss Payne's apparent youth and extreme voluptuousness would have elicited catcalls, at the least, from the troublemakers among the male students. Even a normal private school's hallways would likely have seen some whispered comments behind hands, some jokes snickered at furtively. In Miss DeVille's School, the students were quiet as the grave as they moved purposefully from lockers to classrooms. If many of them followed the sway of Miss Payne's perfect ass, or the bouncing masses that were her giant G-cup tits, they could hardly be faulted for that. But not a one made the least gesture of disrespect. As she reached her classroom and settled behind the desk, Miss Payne scanned the room. She was happy to see that her class was entirely full of boys today. As she expected, each of her young charges were in their seats, books on desks and ready for instruction. They sat ramrod-straight, eyes forward expectantly. Each of them was dressed in the school uniform: gray pants, blue blazer emblazoned with the school crest, white shirt and striped tie. Every one looked freshly pressed and ready to learn. Every one, that is, except Timmy. In the third row he sat, leaning to the side with his feet in the aisle. His book rested on the floor next to his desk, his brown hair was disheveled, and his tie was loosened to allow his top button to be unbuttoned. "Timmy," Miss Payne said quietly. Raising her voice was never necessary, and was reserved for very rare occasions. "You're not prepared for class. Please fix your tie, and open your book to page 512." The other students rushed to the required page as Timmy lazily gazed down at his book, then raised his eyes to meet Miss Payne's challengingly. "Why should I?" he muttered. Miss Payne's eyes widened and she let out an involuntary gasp of surprise. The other students in the room looked up briefly from finding their pages to stare at the jiggling flesh of her magnificent breasts. Then they turned their attention back to their books, and Timmy's rebellious gaze was the only one to meet hers. "Well, I..." Miss Payne started, so surprised and enraged as to be momentarily taken aback. "Timmy," she continued, regaining control, "please follow me to the headmistress's office. Class," she continued, raising her voice as she addressed the other students, "begin reading on page 512. Continue until I return, or the bell dismisses you." With that, she stood up, causing a rippling movement in her mammoth breasts that was distracting enough to momentarily wrest the class's attention from their reading. Even Timmy's extreme misbehavior didn't cause Miss Payne to think that he wouldn't obey her, and he did. As she walked out of the room and strode purposefully to the headmistress's office, he followed, shoulders hunched, apparently accepting of his fate. The walk to the office was silent; neither Miss Payne nor Timmy spoke a word. They passed down the white, spotless hallways, past classroom after classroom. In each, classes of clean, pressed boys listened attentively or read diligently, and each class was instructed by impossibly beautiful, young teachers. Occasionally, a female student could be glimpsed. They sat in their desks looking even more cowed than the boys, unsure, and obviously uncomfortable in their tight, tiny tops and their short plaid skirts. Some of the classrooms had a few empty desks, but neither Miss Payne nor Timmy were able to peer to the back of the room to see what the recent occupants were doing. When they reached Headmistress Roberts's office, Miss Payne held the door for Timmy. He slouched inside grimly, all hint of defiance out of his posture. He took his place in a seat in front of Miss Roberts's desk and waited quietly, as if for an accustomed ritual. Miss Payne, following, looked around the office with more interest. Discipline problems being as rare as they were at Miss DeVille's School, she hadn't often had occasion to visit the office since the first time she could remember seeing it, long ago when she was a student. Miss Roberts was different from the other staff, and kept her distance. The office was old-fashioned, paneled in dark wood. It was free of the sort of bric-a-brac that often dominates school offices; there weren't any athletic trophies or newspaper clippings, of course. The deep red carpeting contributed to the feeling of warmth and privacy. The office was dominated by the heavy old wooden desk that hid Miss Roberts's body below the waist. On the desk there was only an expensive antique pen set and a large wooden paddle with a long, thick handle. "Miss Roberts," Miss Payne began, "Timmy was extremely disrespectful in class just now." There was no elaboration, no appeal to Timmy to explain what he did or why. The boy didn't attempt to argue his accusation. "Well, Timmy," Miss Roberts offered, "I must say you're having trouble lately. You've been here since September, if I remember correctly?" Timmy nodded by way of an answer. "Since September," Miss Roberts went on, lifting an old-fashioned, leather-bound book and finding a particular page in it, "you've been sent down to my office... five times. Today makes six. None February, and then six in the last six weeks. I must say, I would have thought you'd have learned your lesson by now." Timmy slouched lower in his seat, his eyes downcast. He said nothing. "I'm afraid I'm at the end of my rope with you. This is, as you know, your last chance. If I have to speak to you a seventh time, you know what the punishment will be, don't you?" Timmy looked up at her and nodded, still mute. "The seventh time, it will be permanent until graduation. I should think that would be enough of an incentive to help you curb your misbehavior in the future. As this time is the sixth, your punishment will last for a week. Stand up and remove your clothes." Timmy complied. As he removed his clothes, he folded them carefully and placed them in his chair, revealing the healthy body of a boy in his middle teens. When he slid his white boxers off his legs, he stood before the two female staff members with his hands clenched in front of his crotch in embarrassment. Miss Roberts stood up from behind the desk and walked around to stand next to Timmy, picking up the paddle from her desktop as she did. Timmy's eyes focused on the paddle with an expression that couldn't be read; it might have been fear. As he and Miss Payne watched, the headmistress reached out and slapped Timmy's bare ass once, very gently, with the wooden paddle. Miss Payne had only had the opportunity to watch one of the punitive transformations several times, so she stared with interest. She could vaguely remember how Timmy must be feeling now, as his body began to betray him and to reshape itself along lines for which it was never intended. She saw his eyes squeeze shut, then spring open with surprise as he stared down at his body while it changed. At first, all that was noticeable was a slight decrease in mass. Timmy became shorter and thinner, almost imperceptibly. As the changes accelerated, she watched him shrink from nearly six feet tall, until he settled at an inch over five feet. He stared down at his body then, his hands still clenched to hide his cock. He looked years younger, thin, androgynous, and completely hairless. Then the next round of changes began. Timmy's face reshaped itself as the two older women watched. His eyes became bigger, his lips puffier. A light spray of freckles spread across his nose as it became smaller and more delicate. His eyebrows thinned as the hair on his scalp lengthened and lightened, spreading past his shoulders in a long shower of blonde. The changes spread downward, coming faster. His shoulders compressed in as his hips widened and his ass grew out into a sexy, tight, teenage butt. His skin and muscle tone took on the slight padding of a girl in the last stages of puberty. His hands and feet became smaller, more feminine. Finally, Timmy's nipples began to become more prominent. At first, they just seemed erect, but then they became puffy and stood out from his now- narrow chest. They brightened from brownish to a healthy, youthful pink color, and seemed to tighten even more. Then, underneath them, his breasts started to develop. As Miss Payne watched, Timmy's breasts sprouted out from his chest. The changes were coming faster now, and Timmy was breathing hard as his chest grew. It started as two slight swellings underneath his enlarged pink nipples, but they quickly increased in size. They grew past the slight A- cups that signal the beginning of development, and then past the B-cups that a girl of Timmy's age and build might expect to have, still gaining speed. Larger and larger they swelled, passing little half-spheres and developing out into full, generous endowments without stopping. Timmy passed a D-cup, then a double-D, and his breast development continued apace. When Timmy's growing breasts surpassed her own G-cup endowments, Miss Payne reached up to caress her tits unconsciously. The sight of the young boy being transformed into a young girl turned her on more than the earlier transformations she'd witnessed, and she knew it was due to the impressive size of his breasts. Timmy's titties settled onto his chest, finally, at a gigantic size that would have filled a J-cup bra to bursting. They were huge and firm, larger than basketballs but miraculously perky. They stuck out in sharp contrast to the rest of his body, which was much more in keeping with his actual age. Breasts like this would never be found naturally on a girl in her mid-teens or, for that matter, a woman of any age. But there they were, jutting proudly into the air and quivering with each short, excited breath Timmy took. Timmy's hands slid away from his crotch and up to his mammoth tits just in time for the two older women to see the last of his cock slip away inside of him, between the hairless folds of his new pussy. His hands caressed and kneaded his mountainous breasts as a new fire crept into his eyes. His breathing was coming very fast and shallow, now, and his hips were starting to thrust slightly as he unconsciously bucked in arousal. His fingers slid across his breast to pinch his puffy pink nipple, and he let out a yelp of surprise and pleasure. Miss Payne could only imagine how Timmy must feel now. The effects of the punitive transformation were more intense each time. As a boy, Miss Payne had only felt them once. Even that time, though her younger self had only had A-cup breasts and a coltish, immature frame, the arousal was overpowering. That one punishment, lasting only a day, had been enough to teach the young boy she'd been that misbehavior had its consequences at Miss DeVille's School for Wayward Boys. She was thankful that the transformation she had undergone when she'd decided to stay on as a teacher left her with much more self-control, even if her sex drive was still quite high. "Hopefully," Miss Roberts began, drawing Miss Payne's attention from her own reminiscing to the punishment of the current student, "this will teach you to behave yourself more appropriately." Miss Payne could see that the headmistress was moving awkwardly; she was just as aroused by the young naked boy's transition to a young, naked, and extremely busty girl. "Although, as you know, I'm going to make sure to ram the lesson home. Come over here and show me that you know your place as a female student in this school. Show me you know how to do what we both know you'll be doing for the next week." As she said this, the headmistress settled back into one of the chairs arranged in front of her desk. Miss Payne, in the seat beside her, could see how the front of Miss Roberts's skirt was tented out quite obviously. As she watched, Miss Roberts pulled the front of her skirt up, revealing the 12-inch cock that jutted from her crotch. It had far outgrown her panties, which were tangled up in her balls as the long, thick shaft jutted out above them. Miss Payne knew that Miss Roberts had been allowed to keep her dick when she took the position of headmistress, but she'd never seen it before. She'd brought several other students to the headmistress's office for punishment, but had never seen Miss Roberts take such an intimate interest in a student's discipline as she was doing now. Of course, all of the other students had been on their first or at most second transformation. Timmy was being turned into a girl as punishment for the sixth time. As she watched, Timmy moved down to between the headmistress's legs. He was awkward when he tried to get to a kneeling position; his huge new tits tended to overbalance him, and he couldn't see his feet. Once he'd reached his knees, however, he leaned forward, wrapped his lips around Miss Roberts's dick, and started sucking in earnest. From only feet away, Miss Payne watched intently. She hadn't yet had the opportunity to see this part of the discipline process this closely, and she found the sight to be enthralling. The transformed teen's cute face bobbed up and down in the lap of the older woman, his lips stretching to wrap around her thick member. As she felt the student sucking her huge cock, Miss Roberts had reached up to unbutton her top, releasing her breasts from their bondage and playing with them to increase her pleasure. Her breasts, like Miss Payne's, easily would have filled a G-cup bra to bursting, but bras were an article of clothing rarely seen in Miss DeVille's School. Her nipples were tight and hard as she tweaked them with her fingertips, enjoying the sensations that shot down to her cock, currently contained in the wet, luscious mouth of her student. Miss Payne couldn't contain her arousal. Watching the transformed boy blowing the head of the school was too much. She unzipped her own skirt and slid it, along with her panties, down her legs, kicking her clothing away and leaving her bottom half totally naked. Settling back down into the chair, she slid her middle finger down over the soft, silky skin of her hairless pussy mound. She teased the tips of her pussy lips, spreading the juice of her slippery cunt, then plunged her finger inside her pussy, stroking her clit with her thumb. The teacher continued to watch the student suck the dick of the headmistress. Slowly, Miss Payne unbuttoned her top and slid out of it as she continued to manually manipulate her cunt. She was careful not to jostle Miss Roberts's dick out of Timmy's cute female mouth. When her own giant titties were revealed, the teacher stroked them and flicked her nipples as her hand worked unceasingly in her pussy. Timmy's mouth was similarly committed to sucking Miss Roberts's dick. His head bobbed up and down, his blonde hair flying, as his lips stroked the length of her shaft. Her cockhead appeared as he reached the top of every stroke, slippery with saliva and pre-cum, then disappeared into his throat as he took the length of her cock into his mouth. Miss Roberts was bucking her hips in time to the teen's bobbing head, straining with the pleasure of the expert blowjob Timmy was giving. He was incapable of giving anything less. After several minutes of constant stimulation, Miss Roberts seemed to be nearing orgasm. Timmy, instinctively knowing what to do, redoubled his efforts, stroking his soft female lips up and down her male organ faster, sliding his tongue around the head of her cock with more force, pumping her shaft with his hand more quickly. His giant breasts jiggled, hanging from his chest, as the headmistress's moans rose to a higher pitch and her cock began to spasm, spraying jets of cum into Timmy's young mouth. Miss Roberts grabbed Timmy's head, holding it in her viselike grip as her hips pumped her cock into his mouth. She moaned in pleasure as her cock emptied her cum down his throat, and Timmy's moans seemed to suggest that he received equal pleasure from swallowing her thick, creamy cum. As her orgasm finally receded, the headmistress, shaken, released the student. He stood up unsteadily, nearly unbalanced by the huge J-cup breasts jutting from his teenage chest, then wiped a drop of cum that had dripped from his cute mouth to the tip of his chin. "Now," Miss Roberts said, regaining her composure, "bend over my desk. I want to see your naked pussy from behind." Timmy obeyed immediately. From her position, lying naked on one of the burgundy leather office chairs as she slid three fingers rapidly in and out of her smooth, slippery pussy, Miss Payne could see the teen's fantastic body just as well as Miss Roberts could. He was bent over the desk, his legs spread apart and ass-cheeks slightly parted to reveal his tight teenage asshole and his bald, wet pussy. His elbows were resting on the table, and his huge melons were large enough that they, too, were pressed down onto it. He looked back at the two staff members expectantly. Miss Roberts wasted no time. Her foot-long dick, having dipped slightly after shooting its load into Timmy's soft, wet mouth, had regained hardness. It was sticking up out of the front of her skirt. Her breasts, no longer hidden by the top that was unbuttoned and thrown open, jiggled as she took her place behind Timmy's bare, waiting pussy. She slid the head of her cock up and down his slit several times, rubbing it between his ass-cheeks and causing his hips to roll in anticipation of penetration, then slowly slid her organ into his hot, wet pussy. Timmy's ass pushed against the headmistress, deepening her stroke as she drove her cock into his pussy from behind. A moan escaped his lips as the thick meat of her dick penetrated his new female crotch. Miss Roberts's cock slowly pressed into his pussy, sliding deeper into his cunt. From the look of determination on the headmistress's face and the expression of pain mixed with pleasure on the teen's, Miss Payne could tell that the fit was excruciatingly tight. When Miss Roberts hit bottom, her twelve inches buried to the base in the young student's quivering cunt, both of them heaved an audible sigh of relief. As her hands slid to the young teen's slim hips and her own pelvis began to thrust her rigid dick into his stretched pussy, Miss Roberts's look of determination began to melt into a distracted mask of pure pleasure. Timmy, for his part, didn't look to be having too bad a time, either. His mouth was open in a loose "O" of silent moaning as the headmistress fucked him from behind. As she continued to fondle her immense, though not as immense as Timmy's, breasts and finger her wet, smooth pussy, Miss Payne watched as the headmistress picked up the wooden paddle from its place on her desk, turning the long, thick handle around and grasping it by the paddle. As she continued to stroke her thick cock in and out of the teenager's pussy, she positioned the end of the handle at the tightly clenched entrance to Timmy's ass. He moaned then, in what sounded like a mixture of fear and anticipation, but of course he couldn't object. Timmy's moans became louder and more insistent as the wooden handle slid slowly but relentlessly up into his ass. Miss Payne found her own pussy heating up and approaching orgasm as she watched the headmistress double-filling the helpless teenager, stroking her big cock in and out of his pussy while her paddle violated his asshole. Timmy seemed to be minding the violation less and less, however, as his tender young holes stretched to admit the foreign intruders and his hips started to buck back into Miss Roberts's thrusts again. Miss Payne's fingers working in her pussy and her hand stroking her tits pushed her over the edge then, and her eyes squeezed shut as her orgasm shot through her body, making her arms and legs rigid as her back arched with the ecstasy of her climax. When her eyes were capable of opening again, Miss Payne looked up to see Miss Roberts's eyes on her as she continued to double-penetrate the student bent over her desk. "Why don't you climb on the table and let Timmy service you as well? As poorly behaved as he's been, I doubt he's had a taste of pussy since his time here began." Miss Roberts knew that the teachers often rewarded well-behaved students by letting them stay after class and fuck their teachers. It was encouraged. Keeping order only by the threat of punishment was not as effective as training the boys to behave by using punishments and rewards. All the students at Miss DeVille's School had been delinquents and troublemakers at the schools they came from, but fear of the punishment combined with the reward of sex with the gorgeous and extremely busty young teaching staff transformed them into model students in no time. Miss Payne had several students whose good behavior she was rewarding regularly. One of her best students from her morning classes had stayed through the lunch hour, fucking her on her own desk, and she had felt pleasantly satiated with her pussy full of the young man's cum when she had returned from lunch and had to deal with Timmy's insubordination. However, she was certainly willing to let Timmy lick her smooth pussy to another orgasm, so she climbed onto the hardwood top of the headmistress's desk and spread her legs, grasping Timmy by the back of his head and guiding his face down into her hairless cunt. Timmy's tongue went to work at once, sliding along his teacher's slippery pussy-lips. Miss Payne moaned and set both her hands to work massaging her breasts and rubbing her nipples, as Timmy tongued her cunt and sucked her engorged clit. The rhythm of Miss Roberts driving her cock into his pussy and her paddle into his ass pressed Timmy's face up into Miss Payne's crotch repeatedly, rocking her soft, rounded ass on the desk. Each time his face was forcibly pressed into her crotch, Miss Payne felt herself creep a minute bit closer to orgasm. Her hands slid over her giant titties, her palms teasing her nipples, as the teenager licked and sucked at her sopping, hairless pussy. Miss Roberts, at the same time, seemed to be grunting and moaning more insistently now. She seemed to be moving toward a climax herself. Her big, round breasts heaved on her chest as her rapid breathing caused them to leap and bob, and she pulled Timmy's slim girlish hips back, forcing her cock into his pussy with one hand while she rammed the paddle up his ass with the other. Timmy's muffled moans of pleasure forced themselves past the folds of his teacher's pussy, as he was still burying his face between her legs and pleasuring her with his tongue. He was moaning faster how, though, and louder, his breath coming quicker as all three, the headmistress, the teacher, and the student, hurtled toward climax in their sexual triangle. Miss Roberts came first, grunting an unfeminine groan and ramming her cock and paddle into Timmy's pussy and ass as she deposited a second load of cum into the teenager. Miss Payne could see Timmy's eyes widen at the sudden deep violation as he continued to lick and suck her throbbing pussy, but he must have enjoyed it because he almost immediately began to orgasm as well. He collapsed onto the table, his massive breasts crushed beneath his chest, as the climax washed over him like waves on a beach, leaving his petite female body limp and spent. He never, however, stopped lapping at Miss Payne's lovely pussy. His tongue slid up her well-lubricated slit to her hard, sensitive clitoris several more times, enough to push his teacher over the edge and into her own orgasm. Her soft thighs clenched shut around his cute female face, gripping his head and trapping him up against her spasming pussy as she arched her back, thrusting out her G-cup melons and moaning in pleasure. As their orgasms subsided, Miss Roberts and Miss Payne unsteadily disentangled themselves from the teenager collapsed on the desk, with his giant breasts bulging out to either side of his torso and cum dripping from his pussy and his mouth. Both of the staff members began to arrange and don their clothing, leaving Timmy to clean himself up as best he could and get ready for his return to the classroom. * * * * * * * * * * Danny looked up from his reading to see Miss Payne and Timmy returning from the headmistress's office. He had been known that Timmy would be coming back as a girl, but that didn't prepare him for the sight he saw when they entered the classroom. Miss Payne returned to her place behind her desk, looking indecently satisfied. Danny was sure she'd been pretty well fucked since she left the room. She arranged herself in her chair before she addressed the class. Timmy, they all knew, was waiting in the hallway to be admitted back into the room. "Class," she announced when she'd settled into her seat, "unfortunately Timmy will be unable to join us for a week. Please say hello to Tina." Danny was amazed. The one time he'd been transformed, it had only been for a day. That was the third day he'd been in Miss DeVille's School, and he'd thought he could talk back to the teachers like he had in his old school. He'd learned quickly. Being turned into a girl, having everyone call him Dani, and being unable to control himself when anyone else was in the room had left him shaken, and he'd been careful to follow the rules ever since. Spending a day as a tiny teenage girl, completely submissive to everyone around him, was an experience he never wanted to repeat. Danny knew, from the length of Timmy's punishment, that it would be much more extreme than his own had been, but he still wasn't prepared for the sight of Timmy's transformed form when it walked through the door. The girl that Timmy had been forcibly turned into was tiny and petite, and most of her body was so girlish and cute that it was hard to believe she was the same boy who'd been sitting in front of Danny until he mouthed off to the teacher. The fact that it was only made Danny more adamant that he'd never break the rules again. Danny's eyes were drawn, unavoidably, to the one part of Timmy's new body that wasn't girlish and cute. He stared openly, as did the other boys in the class, at Timmy's enormous breasts. They jutted out from the transformed boy's girlish chest, huge and round, bigger than basketballs but nearly as spherical. The uniform top that Timmy had been provided with did nothing to cover them; he was now so busty that it wouldn't button, and he was trying to maintain some degree of modesty by holding it together in front of him. That was useless, since the shirt wouldn't close, and the whole interior curves of his breasts were revealed to his classmates. Timmy walked as quickly as he could over to his seat, and sat down in front of Danny. Danny could see that his classmate's skirt was so short that, when he sat down, it rode up the back and revealed the sexy teenage ass that was split by a thong. Danny's cock, already hardening at the sight of Timmy's enormous titties from across the room, stiffened even more at the sight of the soft, female ass in the seat in front of him. Danny reached out his hand, under the desk, and began to caress Timmy's sexy ass. His classmate stiffened when he felt the hand on his ass, but then relaxed, sliding back in his seat to give Danny better access. Danny's finger slid to Timmy's ass crack, pulled out the thong slightly, then released it and let it snap back softly. Miss Payne looked up from her desk at the noise, miniscule though it was. "Danny," she said gently, "you know better than that. If you want to play with Tina, take her to the back of the room." Danny blushed, but obeyed. When he stood up from his seat, his hard cock tented out the front of his gray uniform pants. It was right at eye level for Timmy as Danny guided the transformed teen up out of his seat and to the rear of the classroom, where a wide padded bench could be found. Sitting on the bench and feeling his hard-on stifled in his pants, Danny said to Timmy, "strip. I want to see you completely naked." The other students in the class had refocused their attention from their reading now, and were staring as intently at Timmy's back as Danny was at his much more impressive front. Miss Payne didn't scold them, of course. This was the one excuse they were allowed for losing concentration in the classroom. And the teacher seemed to be nearly as interested as the class in seeing the young transformed student strip. Timmy didn't hesitate. He couldn't. He opened the front of his useless shirt, exposing his enormous J-cup titties, and shrugged the top off his shoulders and to the floor. His short plaid skirt went next, as he slid it down his legs. Bending at the waist, he gave the class an excellent, unobstructed view of his thong-split ass, but the view from Danny's angle, of his classmate's new gigantic breasts hanging from his chest, dangling and jiggling, was even better. Finally, Timmy slid his thong down over his girlish hips and stepped out of it, revealing his tight, hairless pussy. "Now come over here," said Danny, and Timmy complied. He sat down on the bench beside Danny and lifted his enormous breasts to the other boy's face, letting him lick and suck the nipples and run his hands over the huge expanse of tit-flesh. The class watched intently as Danny's tongue wandered over Timmy's breasts, his hands rubbing the soft, rounded globes. Timmy's head was thrown back and his eyes closed, his mouth sighing at the feeling of his big female nipples being engulfed in a warm, wet mouth. His legs parted, revealing the wet pussy between them, and his slim hips started to rotate slightly, rubbing his pussy-lips against the padding of the bench. While Danny continued to suck and fondle his titties, Timmy's hand reached over to the other boy's crotch. He unzipped his classmate's fly, clumsily because of the angle, and reached inside. Freeing Danny's nine-incher, Timmy began to stroke his hand up and down the length of the shaft, feeling Danny's warm moan of pleasure against the pillowy expanse of his breasts. His hand slid over the boy's penis, feeling the stiffness and the elasticity of the skin. At the end of every stroke, he rubbed his palm against the head of the cock, sometimes eliciting a grunt from Danny. Pulling away from Timmy's breasts, Danny slid his hands through the long blonde hair and gently pushed Timmy's head down into his own lap. Timmy's mouth closed over the head of Danny's cock, and Danny felt the moist, warm suction of Timmy's mouth begin to work its magic on his dick. The class saw Timmy's head bobbing up and down in Danny's lap, the transformed lips sliding along the taut skin of the hard cock, the swaying of the enormous breasts as Timmy's rhythm quickened. They saw Timmy's hands stroking the shaft of Danny's penis as his mouth and tongue worked the head, and they saw him reach into Danny's fly again to free his balls, which Timmy's hand then fondled and tickled. There wasn't a limp dick in the classroom, or an eye trained on a book, as Danny lifted Timmy's head from his lap and pushed back on the transformed teen's shoulders, guiding him backwards to a supine position on the padded bench. Miss Payne's cunt was wet and throbbing again, even after several satisfying orgasms, as she watched Timmy's giant breasts settle and flow across his petite ribcage, and his legs spread to leave his wet, hairless pussy completely undefended. From across the room, the teacher could see the sparkling pussy juice that was covering and dripping from the student's hot cunt. When Danny leaned forward, positioned the head of his straining cock at the entrance to Timmy's pussy, and then slowly slid inside completely on the first stroke, Miss Payne could almost feel it. She made a mental note to keep Danny after class one day soon, to let him give her a good fucking. Danny's back arched as he began fucking Timmy in earnest, contorting so as to suck on his immense titties at the same time. Timmy having become so much shorter as a result of the transformation, it would have been an impossible task had not his tits become so unnaturally large. The teen's enormous, fat titties were so huge as to be up against his chin, and Danny sucked at the hard nipples as his ass clenched and he drove his rigid rod again and again into the prostrate classmate beneath him. Danny's rock-hard cock plunged into Timmy's wet pussy, and it felt like slipping into a warm, moist cave. Timmy's pussy was perfect. It was tight but yielding, completely hairless, and attached between the legs of the hottest girl to ever walk the halls of Miss DeVille's School. As he pounded Timmy's pussy mercilessly, impaling the transformed boy again and again with his rigid dick while he sucked at the monstrous titties that crowned his petite young chest, Danny found himself wishing that Timmy would never change back. Had Miss Payne said that he'd be this way for a week? Danny had never heard of a punishment that long, but he couldn't feel sorry for the sullen, argumentative boy who usually sat in front of him in class. He was too busy fucking him. Danny could feel his body approaching orgasm when Timmy started to come. His high female voice rose in a screech of ecstasy as he whipped his head back and forth, throwing his blonde mane around and causing the huge mammaries on his chest to jiggle and ripple like flesh-colored Jell-O with nipples. The sight of the big bouncing breasts on his transformed classmate's chest pushed Danny along the road to orgasm even faster, and he knew he couldn't hold out much longer. Grabbing Timmy's tight female ass, he pulled himself into the transformed boy's pussy that much harder and faster, trying to penetrate him as deeply as possible. With each stroke, he proved the depths of Timmy's cunt, driving his hard rod deep into the tight, hairless pussy. Danny's climactic groan blended with Timmy's feminine mewling as one orgasm wound down and another began. Danny pulled out of Timmy's pussy suddenly, jumping forward with his cock in his hand to crouch with it over Timmy's immense tits. Timmy's hands slid over his slick, smooth flesh to his cunt and began to masturbate his pussy as Danny crouched over him, moaning and stroking his cock. The still-male boy's body tightened as his cum was ejected from his cock, shooting at Timmy's face and breasts. The creamy ejaculate shot out in several big spurts, covering Timmy's enormous titties, his face, and his neck. Shuddering with the aftershocks of his orgasm, he stroked his cock weakly as he got off of Timmy clumsily, then turned to the rest of the class. Only when he turned around did he see the line of boys waiting to be next to fuck Timmy. Their books were on their desks, forgotten, and every boy in class was standing in line to use their classmate like the filthy whore he'd become, waiting in various stages of undress to plunge their dicks into the transformed body of their peer. "Get back to your desk, Danny," Miss Payne said, indulgently. "I'm sure Timmy has brought enough pussy to share with the entire class." * * * * * * * * * * Ryan's fourth period class was near the gym, so he was nearly always the first to the locker room. He was undressed to his boxers when he heard the other boys start to come in. Something sounded odd. There was an undercurrent of whispering that wasn't normal. He'd only been at of Miss Sheila DeVille's School for Wayward Boys for a week, but he'd already learned that students moved through the halls in almost total silence, and spoke only when spoken to by a teacher. He already knew why. Miss Johnson, the gym instructor, found it odd as well. Ryan saw her come out of the gym office and stand just inside the locker room, hands on hips, her tight, perfect ass barely covered by the athletic gray gym shorts that appeared to have been sprayed on and her giant melons barely contained by her straining sports bra. He turned his attention back to dressing, an action that was made much more difficult by the erection he had sprouted at the sight of his teacher's sexy body. "Why on Earth are you boys making such a... oh," Miss Johnson said. The whispering had stopped as soon as she started speaking, but it wasn't until the entire group of several students made it into the locker room that Ryan saw what had caused her to trail off. It was a girl. Actually, "girl" might not be quite accurate. Most of her looked quite young, only in the middle of her adolescence, but her tits... They were nothing short of gigantic. Huge, watermelon-sized, but very round titties hung magnificently from her chest. Her schoolgirl uniform, with the tiny plaid skirt and the shirt held almost together in a vain attempt to hide her stupendous endowments, was the most arousing outfit Ryan had ever seen. "Who is this?" Miss Thompson demanded of Danny, a boy in the class who Ryan knew slightly. Ryan knew the answer, at least in a general sense. There were no female students at of Miss DeVille's School except for the boys who had been transformed as punishment. "This is Timmy, Miss Johnson," Danny replied meekly. "He was rude to Miss Payne. She said that he's going to be 'Tina' all week." "I might have guessed," the teacher replied. "Well, I certainly hope he learns his lesson this time. But the rest of you must learn to be quieter in the hallways. Well, take him in back and let him change his clothes. I don't suppose we'll get much done in class today." Cowed, the group of boys surrounding the transformed teen moved to their lockers. Timmy's and Danny's were both near Ryan, and as the now-female boy started, as demurely as possible, to strip out of the few scraps of cloth that constituted his schoolgirl uniform, Ryan found that the hard-on that Miss Johnson had inspired hadn't subsided. He stared at every curve and crevasse of his transformed classmate's perfect body, amazed at the swaying of the immense tits and the sweet little teen ass. Timmy seemed to be trying to change clothes without drawing attention to himself, but there was no way he could hide endowments like those. "A week," Danny muttered under his breath, and Ryan strained his attention away from Timmy's naked form to see Danny shake his head. "What's that?" he asked. "Miss Payne said he's going to be that way," he started, inclining his chin toward Timmy's jiggling, female form as he pulled off his tie, "for a whole week. I've never heard of a punishment that long." "I've never seen tits that big," said Ryan. "I thought they were all like what happened to Greg last week?" "What?" said Danny. "Oh, I forget you just got here. No. That was only the second time Greg's ever been sent to the headmistress. That was nothing. Most guys learn after one time. A few screw up again and get the treatment twice. But this joker here," pointing his thumb at Timmy, "can't seem to fly right no matter how many times he gets punished. Each time, they make you bigger and sluttier. As many times as this guy's been transformed, it's no surprise his tits are as big as beanbags." "So... the reason they act like that is because of the punishment?" "Yeah," said Danny. "You think Greg let all those guys fuck him because he liked it? Fuck, no. When you get transformed, you can't be yourself. The way you act, the things you do... you're not in control. The only time you can do what you want is when you're alone. This guy," he jerked his head in Timmy's direction again, "will fuck and suck anything that moves until he gets back to his room. Then he'll probably lie down on his bed and hate himself for it. That's how they get you. There's no way I'm ever stepping out of line again." "So... you've been transformed, too?" Danny was saved from having to answer this embarrassing question when another boy from the next bay of lockers turned the corner into view. The towel wrapped around his waist did nothing to hide his hard cock as he stared at Timmy's very female form. The transformed boy, made slower by the inconvenient appendages attached to his torso, had just finished stripping down to his thong panties. The other boy, whose name Ryan didn't know, reached out to grasp Timmy's panties by the waistband and slide them down over his slim teenager hips and down his female legs. Timmy stepped out of his panties and followed obediently as the other boy led him down past the lockers to the shower room. Ryan joined the crowd of boys following. The rows of showerheads were spraying hot water indiscriminately, filling the shower room with steam. Little droplets of water attached themselves to Timmy's naked body, his female form glistening with moisture. As the boys followed in, Timmy stood in the center of the shower room, the spray hitting his petite body. His humongous tits, their puffy nipples standing at attention, jutted out from his body. He stood with legs slightly spread, his dripping, hairless pussy exposed and visible, waiting for someone to make the first move. The boy who led him into the shower moved forward first. Guiding Timmy by the shoulder, he pushed him forward, bending the tiny female body at the waist. Timmy's titties overbalanced him almost immediately, and he fell to his hands and knees. His gigantic tits swayed dramatically beneath him, nearly touching the floor between his outstretched arms. The boy who had forced him into this undignified position crouched behind him, stroking his erect ten-inch cock. His towel had been discarded, and he was as naked as Timmy was, though the many spectators paid no attention to their still-male classmate's nudity, so intent they were on Timmy's titanic swaying breasts and his upturned teen ass. His as cheeks were parted and his pretty pussy was visible from behind. The boy behind him positioned his long, thick pole at the entrance to Timmy's pussy, then drove the dick into him from behind. Timmy's cute voice gasped in pleasure, and everyone knew when the lengthy rod was filling him all the way from the whimper of ecstasy that escaped his lips. The stiff cock pumping in and out of his pussy, Timmy moaned agreeably at the deepest penetration of every stroke. One of the watching boys, unable to contain himself any longer, dropped his towel, revealing the straining hard-on that every boy watching Timmy get fucked now possessed. This one skirted the coupling teenagers, descending into the steam in the center of the room and kneeling in the hot mist, directly in front of Timmy's face. No convincing was necessary; everyone knew the compulsion that went with the transformation was strong enough. Timmy's mouth closed around the thick head of his classmate's cock, and his talented tongue began to massage the stiff pole. With a cock buried in his pussy and another between his lips, Timmy let out a squeal that informed everyone present that he was having a spectacular orgasm. Some of the students reflected on the shame he would surely feel later, when alone in his room, for the way he was acting now. None of them, however, made any effort to lessen his humiliation. These were the rules; this was what was done. And of course, Miss Sheila DeVille's School for Wayward Boys was very effective in training its students to follow the rules. When the boys pumping their cocks in and out of Timmy's pussy and face finally spurted their loads of hot, creamy cum into him, they got up and moved to let other classmates have access to the horny transformee. Timmy waited on hands and knees, his pussy wet and waiting, his hips still rolling slightly in anticipation of the fucking that had only momentarily ceased. Another boy moved to lie on the floor, sliding under Timmy's body to fuck him from below. Timmy's immense titties hung down from his chest, resting on the body of the boy under him, as the thick, thrusting cock slid deep into Timmy on the first penetration. His pussy was wet and ready, and he began moaning again at the penetration until another boy, crouching in front of him, inserted another cock into Timmy's face. The insatiable transformed boy sucked it greedily into his mouth and buried his face in his classmate's crotch. Ryan was entranced at the sight of the boy he slightly knew, now transformed into a vision of excessive feminine charms, bobbing his head and bouncing his hips up and down as dicks penetrated him in two holes. The transformed teen's girlish ass moved up and down as the dick pistoned in and out of his pussy, and Ryan knew he had to have some release. Doffing his own boxers, he moved into the thick of the spray of the jets, feeling the hot water run over his body as he crouched behind Timmy. His hard cock was begging for release as he pointed it at the difficult moving target of Timmy's asshole, bobbing up and down as he energetically impaled himself on the cock underneath him. Choosing his moment, Ryan slid his cock into the other teen's ass, riding his bucking body like a bronco. The rhythm was problematic at first, but Ryan soon fell into a pattern that worked with, rather than against, the other two boys with their cocks in the fine piece of ass that Timmy had recently become. His cock buried in the hot, tight tunnel of Timmy's asshole, Ryan could feel the cum boiling in his balls as he pumped away, trying to last as long as possible before he deposited his cum deep up in Timmy's back door. The feeling of tightness, of friction, that Timmy's ass communicated to his cock was the most erotically hypnotic sensation that Ryan had ever felt. This transformed boy fucked like the sexiest woman alive. Ryan was glad that he could look forward to a week more of this. Eventually, Ryan couldn't hold out any longer. The jet of sperm spraying from his dick and up into Timmy's bowel seemed more forceful than the jet of the shower nozzles hitting them on the floor. The other two boys fucking Timmy reached their own orgasms, unloaded their cum into Timmy's waiting orifices, and then made way for others. Timmy, moaning regularly from apparently rapturous female orgasms, spread his mouth, his pussy lips, and his ass cheeks, easily accommodating all comers. He kneeled in the center of the shower, taking dicks up his ass, in his pussy, between his tits. He sucked cock and stroked it with his hands. Cum shot at him, covering his back, his face, his ass, his tits. It soiled his hair, then was washed away by the spray of the showers. Timmy fucked like a champion, tirelessly. No matter how many cocks were pressed into him, he satisfied them all, milking the cum from them with his holes or his hands, or the crevasse between his stupendous titties. Each cock was caressed, played with, and then sucked dry. Even when Miss Johnson, tired of waiting for a class that was wholly preoccupied with its shower-room antics, entered the shower, stripped off her clothing and sat spread-legged against the wall for Timmy to lap at her smooth hairless pussy, he still took a dick in his ass, one in his pussy, and jacked off two others in both his hands. A sexual dynamo, Timmy satisfied some classmates two or three times, keeping them past the bell signaling the end of the period and exposing some of his peers to their own punishment for tardiness to their next hour classes. * * * * * * * * * * When he finally staggered back to his room, long past his normal bedtime, Timmy had been fucked more times than a whore on payday. His schoolgirl uniform had rips where overzealous boys had stripped it off of him too roughly, and cum was drying on the skin of his face and body in flaky white patches. He was walking carefully, his pussy and ass having been pounded by penis after penis, and his throat felt sore from the many cocks that had been shoved down it. If one of Timmy's classmates had seen him stagger, exhausted from countless orgasms and the effort of repeated hard fucking, through his doorway, they would have been certain they knew what he would do once inside and cut off from other people. Almost all the students at Miss Sheila DeVille's School for Wayward Boys had been in his position at one time or another, and they had all reacted the same way. The moment the door was shut behind them, the veneer of the submissive, quiet fuck-toy fell away. They looked down at their female bodies in disgust at what they'd been forced to do, and to enjoy. They sobbed uncontrollably at the humiliation they'd undergone, barely sleeping though they longed for the oblivion that slumber would bring. Each of them spent the night in hysterical remorse over the infraction that caused them to be reduced to their present position, and each came forth in the morning resolved firmly never to put a foot wrong in Miss DeVille's School again. Had one of Timmy's classmates seen him once the door shut behind him, they wouldn't have understood or believed his reaction. When the last sliver of the hallway disappeared behind the closing door and Timmy felt his own will reassert itself on his body, he let out a satisfied sigh that suggested happy weariness, not suicidal depression. Instead of flinging himself on his bed, still clothed and sobbing, he grinned and hummed a tune as he stripped off his female clothes and showered to remove the drying cum from his hair and his perfect body. Drying himself off after showering, he admired himself in the mirror, turning to examine his cute ass and gigantic breasts. He lifted each and watched it fall, grinning at the jiggling the action elicited, then walked, still naked, to his bed. Lying down, he began to masturbate listlessly, all real desire satiated but still enjoying his body. "Well," he thought, "that was quite a day. And now I've got a whole week like that ahead of me. I can't wait." "I can't believe I waited so long before I broke any rules. I was so scared of being a girl that I knuckled under just like the rest of those morons, doing anything the teachers asked of me. When I slipped up and got transformed the first time, I thought my life was over." "But from the first time I felt that cock in my little teen pussy, I was hooked. This was it. What I'd been waiting for. When my first day as a girl was up and I transformed back into a boy, my cock was rock hard just thinking about the orgasms I'd had with my little pussy full of cock. I couldn't wait to be a girl again." "And after a week, I'm a boy again. But Miss Roberts said next time, it'd be permanent. Until I graduate, she said. I wonder what would happen if I got transformed again, permanently this time, then tried to escape? That's an interesting idea. If I made it, I'd be outside and a huge-breasted slut for life. If they caught me, they'd probably make me even more slutty and keep me here." "Of course, I'd be stuck as the demure little slut if I got out. I'd have to lay down and give it up to any guy with a hard dick that wanted to fuck me. But that's pretty much what I'd do if there wasn't any mind-control, anyway. When you're forced to act like you really want to act, that isn't really much like mind-control at all." Timmy grinned, his fingers slipping in and out of his wet pussy and his hands roaming over his giant, fat titties. He moaned softly and wriggled deeper into his covers, full of anticipation for the long week he had ahead of him and eagerly planning for the months and years that would follow it. End.

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Inside Out Part 2 The Last of Sheila

Inside Out Part 2 That Last of Sheila? By Suzanne Knight I got up around 7Am showered and shaved, went with a comfortable bra with weighted breast forms that moved naturally when I walked, put on the waist cincher, sheer taupe pantyhose and a gaffe. The Sheath Vee String Vagina had been pretty uncomfortable yesterday after only a few hours. I did understated make up except I still used the dark red lipstick that went with the finger nails. I slipped into the white blouse and the blue...

2 years ago
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Sheila Breastfeeding her Sister

I turned around to find Sheila holding a new born baby in her arms. She sat in the chair asking if I could help her train to breast feed her baby. “When did you have the baby” I asked the 18 years full bloomed girl that she was then. “She is my baby as well as my sister” innocently she responded. I took support of the table as I felt the roof is falling down. I knew Sheila for the last so many years. She first came with her dad, Paul, bleeding in her pajamas about 3 years ago. Paul told me...

Incest
1 year ago
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Sheila Breast Feeding her Sister

I turned around to find Sheila holding a new born baby in her arms. She sat in the chair asking if I could help her train to breast feed her baby. “When did you have the baby” I asked the 17 years full bloomed girl that she was then. “She is my baby as well as my sister” innocently she said. I took support of the table as I felt the roof is falling down. I knew Sheila for the last so many years. She first came with her dad, Paul, bleeding in her pajamas about 3 years ago. Paul told me that...

Incest
1 year ago
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SHEILA 14

--------------------------------------------------------------------------------------------- I couldn't say a word as all I could do was stare at Sheila. Shaking my head I tried to wrap my mind around what I'd seen. {I love you Roger. Please don't leave me.} She loved me? How was that... I stopped as I remembered just how complex the emotion program had become. I tried to say something though I seemed to still be in shock somewhat. True I had started to feel something for her but love?!...

2 years ago
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Sunday session with Sheila

On Sunday morning i went to my neighbour Sheilas house for a promised liaison. Sheila is a 67 year old widow that i have started having some fun with. I arrived at her door at 8am for our planned shenanigans, Sheila answered the door in her dressing gown and ushered me in and upstairs to her bedroom. Once in the bedroom she ordered me to strip and lie on the bed. My clothes were discarded quicker than i ever thought possible and i lay back on the bed propped up on the many pillows. Sheila...

4 years ago
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Sheila choti sister

When she turned fifteen, my sister Sheila started going to the same school as me and sort of got in my view every now and then. Some of the guys would come around sniffing out about my sister, wanting to know how old she was, and did her ever fool around, and that kind of stuff. Well, naturally I’d growl and make mean noises and then go sniffing after their sisters. It wasn’t that I was all that protective about Sheila. It was just that I couldn’t imagine anybody wanting to do anything like...

Incest
3 years ago
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SHEILA 16

------------- Ruslan (short blonde hair, 6'7'') - Leader Serafima (dark red head) - support/medical Karina (blonde Hair) - Sharpshooter sniper Timur (Dark hair 5'2''} - computer/hacker expert Egor- Electronics expert Stas - Explosives expert Pibald group ------------ Evelyn (Auburn hair) - Leader former wife of General Gance/sniper Christine/Chris (blonde) - personal combat expert- Evelyn's daughter Trina (red head) - Tall muscular, armed combat, Chris's lover...

1 year ago
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Inside Out Part 3 The Return of Sheila

Wednesday came and Sam and Dr. Inga Carlson a plastic surgeon showed up around 10 AM. Dr Carlson was a tall, rather severe looking woman about 50. She asked me to strip down to my shorts and gave me a once over physical then poked and prodded all around my body. She spent a long time studying my face. She took a brief medical history from me but asked if I could please answer in my femme voice. I complied but it did seem weird. She was typing into a laptop all the time. Finally she...

3 years ago
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Hot Sheila

Sheila and I have had some pretty wild escapades together but one stands out in my mind as probably the wildest. It was Halloween, and we had planned to go to the Santa Monica Street Fair where every year about six blocks are cordoned off and people come from all over to show off their costumes. It’s always a meat-fest and not unusual to see many girls and guys walking around almost naked or wearing so little they might as well be naked. As usual I was going to be part of the spectacle. I...

2 years ago
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Sheila

One?Please?, she said, ?I want you to come with me to pick out a new dress.?Kathy knew that I didn’t like to go clothes shopping with her.  She always took so long to make a decision, always having to sort through all of the racks of clothing, always asking my opinion on one or another, and always ignoring my advice.  I quickly scanned through a laundry list of excuses in my mind, but before I could utter a protest she said, ?Look, I need something new to wear to work, and besides, you could...

2 years ago
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SHEILA 15

--------------------------------------------------------------------------------------------- Timur was still cursing when they pulled off the road. "Comrade? What has you so agitated?" Timur's head snapped up as he looked at Ruslan with a startled look. "I have encountered something I have never seen before." Timur said with great confusion in his voice. "That is no small thing for you." Ruslan told the smallish male a hint of concern in his voice. Timur was nodding as he wasn't...

4 years ago
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Sheila

Well, like most guys, I never thought it would happen to me. I was like everybody else raised in the fifties and sixties — well, not everybody, but most. I grew up thinking that "queers" and "fags" were lower life forms if they were alive at all. Now it's a new century and things have changed. And with the times, so have I changed. It didn't happen all at once and it took a lot of soul searching, but I've "crossed the bar". Here's how it happened... Sheila was promiscuous. I knew...

2 years ago
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Sheila Gets A Surprise

Walter and Sheila are early sixties and sexually active. Walter has always wanted to share Sheila and this is how it happened. Walter had two mates who lived nearby, Don and Bob. One afternoon while the three were chatting Don suggested they have a game of golf which they all agreed was a great idea. To spice things up Bob suggested a little side bet would be a good idea, Walter was a little short of cash so it was agreed that if he lost he could find another way of paying.They set off to the...

Mature
2 years ago
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Sheila

This is a rework of the original. I removed most of the swinging stuff and made it a true romance. I also tried to clean it up a little more. I hope you enjoy. * I was walking through the terminal at the Madison Wisconsin Regional airport when I heard the loud scream of a little girl about 4. I turned and saw this little tyke crying. I walked over and knelt down and asked what the matter was. ‘I can’t find my mommy’ she wailed. I picked her up and carried her to the ticket counter. I then...

2 years ago
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Wayward Wifes Punishment

                               Wayward Wife's Punishment                                                                                   Chapter 1                                             Prologue        Years ago, when beginning the writing of this story, there was no intention of turning it into a novella or longer. The initial concept however quickly changed from a "hit and run" sex and violence short story to this epic of self-discovery on the part of the protagonist. This work still...

4 years ago
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Just a word with Sheila

That Tuesday morning I noticed that my sweet secretary Sheila was not dressed in her usual scrubs; but she was clad in a sexy black skirt and a tight fitting white top. I commented that she looked quite sexy. But then she surprised me; as she bent over and showed me her black string with barely covered her dark asshole.After the ordinary Tuesday’s meeting, Sheila asked me if she could have a quick word with me. She walked into the ladies room and pointed me to enter there.As soon as the door...

3 years ago
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Mum Dad and Auntie Sheila

It was approximately 8:45pm and dad was out as usual but mum was sat downstairs with her friend, I called her Auntie Sheila, she wasn’t my real Auntie but that’s what I called her. They were sat on the sofa drinking wine, I was sat at the top of the stairs, our room was open plan so I could see the TV from there, and where they were sitting, I was 15.As I watched the TV I noticed mum leaned over and whispered in her ear, then they both laughed, mum put her wine glass on the coffee table and...

2 years ago
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Denise The Submissive Mom Chapter 22 Sheila one week later after party

On the 70inch tv screen behind her , Sheila could see that Rocky had made time this week to meet a new submissive, she would learn later that her name was Gwen a 55 year old bank executive , she was sucking her son's giant dong , rather choking on it . She was dressed fashionably , rather businesslike , Rocky had hypnotized her as she was leaving the bank & they went to her home where they were met by her retired husband Norman who he brainwashed also. Sheila noticed that Gwen was stacked &...

1 year ago
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Sheilas Humiliation

The Humiliation of Sheila By Steveswitch33It was indeed very humiliating for Sheila Johnson, her husband was in the front room, while his wife was being force fucked by a white man. It started when they moved back the Eau Claire. They hired a local moving company from the Chippewa Falls area called Rodryder Movers.Rod Ryder was the head man of the moving crew, he just sent his people home and he was going to assist Sheila in organizing things, while her husband Steve watched basketball in the...

3 years ago
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JuniorChapter 16 Sheila

Upset was not the word for it. I had seen Charlie upset lots of times when we were roommates at Cromwell and later at Pontiac. This was different. Charlie was mad, not angry mad, this was foaming-at-the-mouth mad. I didn't blame him, nor did I blame Sheila for letting her son find us on the bed in my room, kissing. I blamed myself. I should have stopped it before it began. Refraining from kissing a married woman, albeit a newly married woman who had come into my room and initiated the kiss,...

3 years ago
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KT LLCChapter 5 Sheila Reneacutee Schwartz hereinafter the Bride

Interlude: 25th Anniversary Cindy: "When Mom talks about the Merger, she is referring to the household staff. Dad means business. After all, it's still his thing. Mom had all real property. Dad wanted to make sure they both got a fair share of the company. I gather this was not trivial." Sheila: Showering together was nice. There was no sex, though a fair amount of pinch and tickle went on. What was nice was having someone to shave my hard to see places. In return, I lathered Sean and...

3 years ago
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A Date With Sheila 54 Years Part 2 What A Fuck

Just a recap of the last session. Sheila my new found love is 54 years old and I Mohan Reddy am 52 years. Sheila has a figure of 36/34/38 and height 5’9” and I am 5’11 “ and an asset of 6”. To continue with the story. We met at the gym and since Sheila’s hubby was abroad in Bangkok this is her enjoyment. Sheila had the food ready. We came and I poured 2 vodkas for us. We started drinking and began dancing. I did not tell you that after coming out of the bath we did not put anything on. We were...

2 years ago
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Hearing Sheilas moans in the next room

My Boss informed he would send me to a conference round in a far city and he gave me the choice to pick up my own female companionship.I used to travel with Angela, a very efficient but boring lady. She was older than me; a very good looking woman, longtime married. But she was hetero and had never accepted my sexual insinuations…This time Angela was ill; so my new choice was Sheila, a skinny redhead in her early thirties, married and social. She was also a real workaholic…While on the plane to...

2 years ago
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Threesome With Sheila Radhika 8211 Part II

I am a 25-year-old guy working in an MNC with a handsome salary. My height is 5’10 and I am having an athletic build, which makes me look sexy. I date women who are looking for some kind of fun. I also come across various women who just want sex and I serve them as well. If you feel like having a great massage and/or something more than that, mail me at I keep traveling due to my job and this gives me access to most Indian cities. I am a bodybuilder and while in the gym, I learned the art of...

3 years ago
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showering with Sheila

A continuation of my last story.After my quick fuck with Sheila (my 67 year old widowed neighbour), we both went into the bathroom, where i stripped Sheila of her sodden cum soaked black granny pants and her tee shirt and bra. Those and my tee shirt were quickly discarded on the bathroom floor as we clambered eagerly into the shower. I played with her saggy boobs, circling her massive stiff nipples with my fingersas i tried to cup those magnicent hangers. Sheila pressed her back against the...

1 year ago
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A Date With Sheila 54 Years Part 1In The Gym

Hi, this is Mohan Reddy again with a recent story of how he met a lady of 54 years, made friends and made love. I am a 52-year-old who stays alone in Indore due to work. The lady is my dear Sheila. She is a lovely lady with a cute figure. Not fat for her age but has flesh at the right places. We met recently at the Gym when we went for a workout. I go daily for the treadmill and so does she. I have been seeing her for the last week come to use the treadmill and sit for a while looking around...

2 years ago
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Finding Sheila

The interface to the biological unit was still active. The previous night, the Law Master had not severed the link and the AI engine had been left connected prior to and during the biological unit’s sleep cycle. The Law Master had mated the biological unit. The A.I. Engine was still interfaced. The process was strange and disconcerting. Technically it would be unlawful for a Law Master to mate with a Field Agent biological unit under their supervision, but for some reason he had received...

2 years ago
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JuniorChapter 19 Gladys Sheila Gladys

Gladys wanted to stay in my room and I let her. I didn't know if she was afraid of Charlie or if it was for the reason she gave; she liked the way I fucked. "Did you mean what you said about my tits?" she asked, snuggling against me so I could feel her nipples bore into my chest. "Yes." "Charlie never says nice things to me the way you do." "I know." "You're sweet. But, God Damn, you can be mean, too!" "I know." "You're not generally like that, are you?" Remembering...

4 years ago
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The Empire Book 3Chapter 20 Sheila and other Allies

Jason had just completed dinner with Cassius and Alana, Razza, Celia, Felicia, Gamma, Jonathan, Norbert, and Philippa; when he received the notification that the fleet had arrived from Parzool. Cassius very much enjoyed the meals at Jason’s house and eagerly accepted each invitation, unless he had pressing Empire business. He also enjoyed the whole household, with its diverse members and resulting interesting and stimulating conversations. The Queen invited them up to her ship for a brief...

3 years ago
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Cumdump Sheila 8211 The Beginning

Jake didn’t sleep much last night. He kicked the sheets and climbed out of bed with a curse. “That fucking bitch shattered my life, and now she won’t even let me sleep in peace,” he muttered to himself. It’s been more than a month, but he still couldn’t get her out of his head. He wandered around his one BHK apartment, lifelessly brushing his teeth. Then he heard the doorbell ring. He opened the door to find his uncle and his cousin smiling pleasantly at him. Shit! Jake had totally forgotten...

Gay Male
2 years ago
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Inside Out Part 5 Sheila is on the Run Again

Inside Out Part 5 Sheila's On the Run, Again I was enraged by Agent Harrison's not so subtle threat. But what troubled me even more was that he was right. If I valued my life I had to cooperate. When I calmed down a bit,I googled Congressman Santini. He was on his third term in Congress, married with two teenage children. He had made quite a fortune in the late 90's Internet boom by founding a company and then taking it public and finally selling it to huge technology...

4 years ago
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Dumping Sheila on Valentines Day

Valentine’s Day surprise leads to a real eye and mouth opener when cheating girlfriend gets caught giving another man a blowjob. ‘So, Paul, you didn’t tell me. Where are you taking me for Valentine’s Day?’ Sheila looked as hot as a house fire. She always acted so coyly innocent whenever she looked so sexually arousing, especially when she knew she was in for a surprise. Only, in the way she was acting, she didn’t look so innocent wearing that dress. She looked guilty, like someone trying to...

4 years ago
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Sheila Meets a Neighbor

Jerome was one of the earliest black studs in my stable.Back in '76 I had a basement apartment and he lived upstairs.He met me,as a female,one day when I was returning from grocery shopping.I was dressed casually in a sleeveless maroon turtleneck,mid-thigh jean skirt and a gaff under sheer nude hose with tan,3" high-heels.I wore a short blond wig of natural hair and light make-up.He walked up to me,wearing a wife beater t-shirt and sweat pants with sneakers, as I began to unload my groceries...

3 years ago
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Sheila Meets a Neighbor

Jerome was one of the earliest black studs in my stable.Back in ’76 I had a basement apartment and he lived upstairs.He met me,as a female,one day when I was returning from grocery shopping.I was dressed casually in a sleeveless maroon turtleneck,mid-thigh jean skirt and a gaff under sheer nude hose with tan,3′ high-heels.I wore a short blond wig of natural hair and light make-up.He walked up to me,wearing a wife beater t-shirt and sweat pants with sneakers, as I began to unload my groceries...

1 year ago
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The New Girl Sheila

I was sitting at my desk when my boss James came in and trailing behind him was a new girl that I had not seen before. "Carmen" he said "This is Sheila" "She will be assisting you with some of the new specs we're doing" he added and I reached up and gently shook her hand. James explained the work she was going to be doing with me and as he did I kept looking over Sheila now and then. Young, nice figure, good looks and a good set of tits I thought to myself and I was hoping I could get to see...

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