Cheerleader's Panty Boy free porn video

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Author's note: this is actually an older story that I wrote almost 15 years ago. A gentleman who has been encouraging me to write these sissy stories suggested that I post some of my older work online here, so that all of my stories would be available to read in one place. It gets a little dark, and I can see how my tastes have changes since 2003, but I still enjoy the story. I hope that you will as well. Enjoy; Sissy Michelle Cheerleader's Panty Boy Steve began crossdressing when he was a young teenager. At first he liked to masturbate into his sister's panties, but that quickly progressed to the point where he was masturbating while wearing his sister's panties. By the time he was a sophomore in high school and his sister Staci had moved away to college, Steve would lock himself in his room when his mom was off at work. He'd dress up fully, wearing panties, bra (he and poor Staci were roughly the same chest size) plus a frilly dress that Staci had left behind when she moved out and a pair of his mom's pantyhose that he'd rescued from the trash. Steve would sometimes sneak down to the kitchen and steal a carrot from the vegetable bin. Then back up to his room where the carrot, liberally greased in Crisco, would be forced into Steven's bottom while he jerked off. It never took more than just a few pokes by Mr. Carrot-dick and Steven was shooting off into his panties. Sometimes Steven wondered if he was gay or something, and the thought really disturbed him, but he justified his actions saying that everybody jerks off. And as long as he didn't do it with a real man, a carrot wouldn't make him into a homo. His dress up sessions became more frequent and more daring. Once, when his mother was away for the weekend, Steven had gone all out. He painted his fingernails and toes. It was a dark-red mess; splattered all over his fingers, but Steven thought the red nails looked extra sexy stroking up and down his cock. He had chosen a larger carrot this time, and he loved the way it's bumpy ridges made him feel. In a fit of passion, Steven turned the vegetable around and shoved the thick end inside him. He winced a bit, but there was no denying that the thicker end felt better than the thin pointy one. And it made him feel so sexy! Steven was furiously pounding away at his cock and bottom, and he was so caught up in his fun that when he reached his climax, Steven straightened up and the carrot snapped off inside him. At first he panicked, thinking that he'd have to go to the hospital and everybody would think he was a queer! But then he realized that the carrot wasn't stuck, although it did make him feel all nice and full. Usually after an orgasm, Steve would clean up and put everything away, but this time with the carrot still inside, he just didn't want to stop. So he sauntered to the bathroom and helped himself to some of his mom's makeup. Lipstick, mascara, blush and blue eye shadow. He looked like an over-made up whore, but Steven loved the look, especially as he stroked his cock for his second and third orgasm of the past fifteen minutes. After that, Steven decided that he would be a little more daring. Steven started wearing his sister's stolen panties to school twice a week on the days he didn't have gym. He thought that nobody had noticed, but Mary Ramses had spied his visible panty lines one day while he stood in front of her and a few of her friends in the lunch line. She smiled as a plan formed in her head, and then she tapped her prey on the shoulder and asked him to grab a lunch tray for her. When Steve reached up to get the tray his shirt rode up and Mary was looking directly at his waistband. Sure enough, there was just a sliver of pink material showing through. "Thanks for they tray," she said and then leaned forward and added, "Nice panties too." Steve went into pre-adolescent shock right there and then. Mary was one of the most popular girls in school. She was a senior, the head- cheerleader to boot. Steve hadn't ever even had a girlfriend, and now Mary Ramses was going to humiliate and make Steve's life into a living hell. He sleep-walked over to an empty lunch table and sat picking at his food, unable to do anything other than think about the many ways in which Mary Ramses could torture him. His life was over, although his penis was rock- solid thinking that maybe it was just beginning. He looked over at Mary and her cheerleader friends and was embarrassed to find that they were all looking over at him and laughing. Mary smiled and gestured for Steven to come over, but Steven turned away with a shudder and went back to picking at his meal. But Mary wasn't so easily deterred. She detached herself from her friends and strutted over to the sophomore that she ordinarily would never have even noticed, she being a senior and all. Mary leaned in close so that Steve was enveloped in the cloud of her perfume, then putting her hand right on the panty line on Steve's inner thigh, she said, "I like a man who's in touch with his feminine side." Noticing the bulge growing next to her hand she added, "it looks like you do too." Mary stood up and looked down at Steve, who still sat in a stupor. When she realized that he was unable to respond, unable to even look at her, she laughed at her power over the poor kid. She took a moment to consider her next move, and then she pulled a ballpoint pen out of her purse and scribbled her phone number on his hand. "Call me tonight at seven," she whispered and then wheeled and walked away. Steve spent the rest of the hour staring at his hand. Mary Ramses had given him her phone number! It was simultaneously the very best and the very worse thing that had ever happened to him! Mary Ramses had noticed him! Oh, Yes!!! Oh, God No! Did she like him? No, that couldn't be it. She was only going to humiliate him--after all senior girls only went for senior boys, and cheerleaders only went for football players. Still, hope springs eternal. Maybe, just maybe Steven thought, hoped and prayed, maybe Mary Ramses had really liked Steve! Maybe she didn't care about his panties! Maybe she thought it was a turn on! Maybe he was out of his mind and his life as a normal high school kid was over. The bell rang and startled Steve out of his conflicting fantasies. He stood up and trudged off toward class. Mary and several of her girlfriends sat by the entrance, giggling and pointing as he passed. Just as Steve got to the door, Mary suddenly called out, "Steven, come here for a moment." Slowly Steve turned to face the girls. Five senior cheerleaders. It was worse than a firing squad. He summoned his courage, cleared his throat and said "Yes, Mary?" His voice cracked in nervousness, and the girls burst out into laughter once more. Mary took pity on the obviously petrified boy and pulled him off to the side. "Steven, I think I might have made a mistake," she said. Steven deflated and quickly offered to go wash the numbers from his hand. "No, silly," she teased. "I gave you my phone number, and I expect you to call me tonight at seven on the dot. But I'm not sure I like having it on your hand, out in the open for everyone to see like that." Steven could understand her sentiments, and immediately stammered that he would write on a piece of paper and never show it to anybody ever. Or he would memorize it. Anything she wanted. "No, Steven. I don't want to run the risk of you forgetting my number." Mary pretended to think for a moment before a wicked gleam filled her eyes. "I've got it," she smirked and then her eyes suddenly went ice cold. "Why don't you go to the bathroom and write my number on your little pee pee. I'm sure it's big enough by now to get all seven digits on it." Steven immediately went into a blustery but incoherent affirmation of his manhood. Mary silenced him with a finger to his lips and looked him sternly in the eye. "Then it's settled. Go write my phone number on your penis, pull up your panties, wash your hands and call me tonight at seven." "Oh yes," she added almost matter-of-factly, "you'd better not jerk off or else it might rub off." More laughter from all the girls and Mary almost seemed to be skipping as she rejoined her group and left the lunchroom without giving Steven a backward glance. Teachers ushered students off to class, but Steven snuck off to the bathroom. He entered a stall and lowered his pants, making sure that his sister's panties didn't fall past his knees. Now Steven had the sex drive of a normal teenager, and he was always ready to masturbate, but never before had he ever been so rock hard and horny. His cock throbbed in synch to his heartbeat, which was pounding a mile a minute. Steven stared down at his shaking cock, the pretty pink panties he was wearing and at Mary's phone number etched on his hand. He wondered what color panties Mary wore, and his penis twitched violently at the thought. He wondered if she liked lacy panties? (twitch) of pretty silk ones? (twitch, twitch). Even plain cotton panties would be fine. Maybe one day, especially since Mary knew and liked it when boys wore panties (twitch), maybe one day Steven could steal a pair of Mary's panties (twitch, twitch). He wouldn't wash them ever, but wear them while they still smelled all girly. Twitch! Twitch! Twitch! Steven threw his head back in fantasy and moaned as he ejaculated. He came so powerfully that some of his jizz rebounded off the partition door and splattered across his upturned face. It was the most amazing orgasm of his young life, and he hadn't even touched his still-pulsing penis. Steven sat there panting for quite some time, and when the droplets dribbled down into his mouth, he swallowed them before he could realize what he was doing. The salty goo snapped him out of his post-orgasmic bliss just as it disappeared down his throat. Steven panicked. "Oh my God," he whispered to himself, "I just ate cum! That makes me gay!" And at that thought, Steven suddenly began vomiting. In between his retching, he heard the door to the bathroom opening and heavy footsteps stepping up to the stall. There was a pregnant moment while Steven lay paralyzed with his head still in the toilet. If whoever was on the other side of the door looked down, he would surely see Steven's pink panties now pooled around his ankles. Steven tried to keep very still, but he could hear breathing just outside the stall door. Then a deafening knock slammed through the bathroom. "Son," a deep voice asked. "You okay in there?" Steven found he couldn't answer. He had just turned gay and now this man knew it. He had seen the panties, and could probably smell the jizz dripping down the partition. As soon as he opened the door one of two things would happen. The man would look at Steven and immediately know that he was gay and either beat him up if the man was straight, or if he wasn't, then he would shove him up against the wall and rape him. That's what homos did. Steven was only sixteen, and his inexperienced mind could only see these two nightmare possibilities. His world was spinning out of control. Things were getting dark. Somewhere off in the distance, somebody was knocking, but it sounded like the sound was coming through water. It was so faint, so far away, and getting farther, and farther... Steven woke up in the nurse's office. He was lying on the couch with a felt blanket spread out over him. He moaned and tried to sit up, but Nurse Schmidt slowly pushed him back down. "Zere, zere," she said in the German accent that she hadn't been able to lose since coming to American ten years ago. "Stay down, mein dear. You had us all vorried. I called your muzer. She'll be here soon, ya? You just lie zere und rest." Steven had finally calmed down, and he even fell asleep for a moment while the nurse wiped the sweat off his face with a warm wash cloth. A bell woke him, and he could hear the roar of student feet stampeding just outside the door. The nurse's office was just off the reception area, and he froze up once again when he heard the door open and the school secretary call out "Hello, Mary." "Hi Mrs. Beardall. I heard Steven fainted." "Really? How do you know Steven?' Mrs. Beardall asked warily. "We're friends," Mary answered confidently and brushed past the woman and into the nurse's office. She laughed softly as she saw Steven; wide-eyed and shaking in terror with the blanket pulled up to his chin. "Oh, Steven," she mused. "What are we gonna do with you?" It was at that moment when the tornado that was Steven's mother whirled into the room. Mary stood aside and let mama claim her baby boy, smothering him with kisses that were far too embarrassing for a high school student. After getting a few instructions from the nurse, she drew Steven to his feet and ushered him out the door. There was a moment as Steven passed Mary when she smiled at him and mouthed "Call me." Steve's mom took him home and put his straight to bed. Stevie was her baby, and after her divorce she found that she had become even more maternal then ever. Steven was a bit groggy, so his mom started to help him take off his shirt and pants. Suddenly Steven snapped out of his funk and twisted like a greased pig. "I'm fine mom, let me go," he cried out in panic. Mother's intuition kicked in and she suddenly realized what was going on. Steven was wearing those damned panties again and didn't want her to know about it. Well, too late honey. A mother notices these things. She sighed and closed the door, thinking that very soon she was going to have to sit him down and have a long, difficult talk with her boy. Steven lay in bed wearing nothing but the panties, fingering the cum that had dried on them. He watched the clock and wondered what else could go wrong today. Soon the whole school would be calling him queer-boy! He just knew it! At 6:00pm Steven began to feel woozy again, although his cock was still rock hard. By 6:15pm his head was aching and so was his cock. At 6:30pm he had to lie down to keep from passing out in frustration. Finally, he locked the door to his room and began to trace the outline of his cock through the sheer pink material that had gotten him into so much trouble. He hated that these panties turned him on so much, but he was unable to do anything about it. He reached out and no sooner did he touch himself than he was wracked with a violent spasm and a single drop of cum started to ooze through the silky underwear. He stopped just on the brink of his orgasm, remembering that Mary had told him not to play with himself. So he steeled himself and obeyed, but was still left with a tantalizing need to reach a climax soon. Steven closed his eyes to ward off temptation, but was left with visions of Mary, stripped down to her bra and panty, and Steven wearing a matching set. They were fucking each other. It was too much. It was 6:45 and he was in agony. "Fuck it," he told himself and reached for his cock. But just as he touched himself the phone rang. Steven froze. He somehow knew that it was Mary. Sure enough, his mother was calling up the stairs, "Steven! Telephone. Are you feeling well enough to talk?" "Got it, Mom," Steven screamed and lunged for the phone in his room. He waited until he heard his mother hang up the downstairs extension, then he ventured a tentative "Hello." "Hi Steven," came Mary's full voice through the telephone line and directly into his head. "I hope you're feeling better, honey, 'cause we've got some things we'd like to discuss with you." Steven swallowed and tried to find the remnants of his masculinity. "Oh, sure Mary," he ventured, "I was just faking that. Wanted to get out of a History test." Mary wasn't buying it. The sweetness in her voice disappeared and was abruptly filled with a deadly seriousness that told Steven that she wasn't to be trifled with. "Listen, you little sissy punk. Who do you think you're fooling? You're nothing but a little panty boy, and probably went right home and jerked off into your pretty panties. That's why I called, I figured that you'd rubbed my phone number off from beating your meat so hard. You'll have to be punished for that, but the important thing, you little punk-ass fuck, is that you realize that if you piss me off, I can make your life into a living hell. I can have you beaten up. I can make sure that everybody in school thinks your gay..." "Please, no, Mary!" Steven cried out from the depths of his heart. "What do you want? I'll do whatever you say." Suddenly Mary's voice was all sweetness and light. "That's better honey. Listen, Steven, we can be best of friends or we can be bitter enemies. If you want to be our friend, you should come back to the school. We'll be waiting at the gym. Be there in 20 minutes" "We'll?" Steven squawked. Mary ignored him. "And don't forget to wear your pretty panties. And I'd love it if you could find a bra to go with it." "But I'm sick. My mom won't let me..." Mary had already hung up. What to do? Steven saw disaster on every path. If he showed up wearing panties and a bra, he'd probably find the football team waiting there to fuck him. If he didn't show, Mary would probably tell the football team that he was gay and tell them to track him down and fuck him. Either way he was fucked. And then Steven's mom made his choice for him. She knocked softly on the door and asked "Sweetie, are you going to be okay? I've got to go back into the office." Steven recognized fate and mustered up his confidence. "Yeah, Mom. Everything's fine. Thanks." His mom sighed and realized that he was probably masturbating again. That's all he seemed to do these days. She took some small measure of comfort in the thought that if he was jerking off again after such a traumatic experience, well that certainly meant that he was going to be okay. Steven waited until he heard the car pull out of the driveway and then he exploded into his sister's room where he found a sexy leopard print bra. Staci had never been all that big, so the bra cups actually cupped his flesh nicely. And while he was rummaging through the lingerie drawer, he spied the matching leopard print bikini. Steven discarded the cum-spotted pink panties and slipped into the fresh pair. In for a penny, in for a pound he thought, and shimmied into a pair of his mom's pantyhose. Then he threw on some jeans and a sweatshirt and ran out the door. Too bad I didn't have time to do my nails, he thought. I bet Mary would really like that. Fifteen minutes later he was standing outside the gym, watching as Mary and the other cheerleaders went though a late-evening practice. He was terrified, but unable to stop himself as he slunk into the back shadows. Mary spied him immediately. She turned practice over to her co-captain and then bounced over with a few of her friends. They seemed positively giddy to see him. Melody, who Steven thought was by far the best looking of all the senior cheerleaders came right up and hugged him. "Oh my God, Mary. You were so right!" She said. "He'll be darling!" Steven was enveloped by a whirling mass of femininity in cheerleader uniforms. They pushed and pulled him forward, and before he knew what was happening, Steven found himself standing in the high school holy-of- holys: the girl's locker room. Mary forced him to his knees as Melody locked the door. They surrounded him and before he could object, they stripped him down until he was kneeling in his sexy lingerie, looking up at the five most popular girls in school. "Look, Steven," Mary finally began, "You like wearing panties. Pantyhose too, I see. Which is okay. I never could understand why guys would want to wear those itchy boxers when they could wear silky, pretty panties like mine." At that, Mary dropped her skirt. Steven's jaw followed it to the floor. Melody added "I usually like to wear lacy thongs, but we have to use these stupid Lycra bottoms with our cheerleading uniforms." And from behind him Jancey agreed, "I hate these fucking bottoms. They rub me raw and leave me itching for a little relief." Steven turned to acknowledge her comments and was stunned to find that all five girls had completely removed her cheerleader uniforms. Steven had never seen a vagina before. Here were five, and they were closing in on him. Mary pulled him around to face full front. There was something in her eyes that kept his attention riveted on her, even though he could tell that the other four cheerleaders were fingering themselves just off in his periphery vision. "Here's the deal," Mary said while pulling off her top to expose a perfect pair of milk-white breasts. "We're the senior cheerleaders. We could date anybody we wanted to, but we only date the starters on the football team. Which is fine if you just want to be seen, but those guys only want one thing..." "Slam, bam, no thank you ma'am" came the answer from Tiffany behind him. Melissa laughed and pulled Steve's gaze back to the front. "Well, we need our fun too. And that's where you come in. You're a nobody in this school, but we can make you into the most popular boy here." "But not some jerk who goes running to his friends saying that he fucked a cheerleader," Tiffany spat. "Fucking David Billingsly!" Jancey agreed. "That's where the panties come in," Mary said. "You're going to wear our panties everyday from now on, so we know that you'll be on your best behavior. Every morning, we'll give you a new pair to wear during the day. You can jerk off into them at night, just as long as you hand wash them at home and give them back to us the next day." "Wait a minute," Jancy interjected. "How do we know that he's worth it? I'm not going through all this if he can't bring me off." Mary was laughing once again. She knelt and looked Steven square in the eyes, spreading her knees so that the scent of her arousal wafted up to Steven's nose. "Here's the deal," she said. "We know that you love being dressed up in frilly lingerie. The hard-on underneath the pantyhose tells me that you will love what we've got in store for you. We will make your dreams come true. But you've got to give something back to us. You'll make love to us with your mouth whenever we want you to. Wherever we want. We'll keep it all discrete, but basically you'll be our little sex slave." "You take care of us, and we'll take care of you," Melody added and snaked her tongue into Steven's ear. "Hell, if you do me right, I might even let you fuck me one day" Melissa said. "Then again, do me right enough, I might let my boyfriend fuck you," Mary said and was pleased to see Steven's cock jerk once underneath her hand. Soon, there was a dark pool spreading across the front of his panties, and all five girls were clapping and saying "Looks like we have a winner." Steven was then put to the test. He was pushed down onto the bench and Jancey straddled his face and commanded him to "lick." Steven did his best, and was finally rewarded with a flush of musky juices that he swallowed down. "Not bad," Jancey said as Melody pushed her aside and mounted up. Melody was much more instructional, and Steven found that she was easy to please. Tiffany quickly followed, but she had been fingering herself as she watched the preceding action, so she flooded his mouth with her juices just moments after she straddled his face. Melissa was a much tougher nut to crack. By this time Steven's untrained tongue was worn out and protesting its unexpected workout. But Melissa was relentless, and she rode Steven until he was ready to drop. Finally, she screamed out in victory and collapsed in an orgasmic heap, her vagina still covering Steven's now-raw mouth. That left only Mary, who strutted over to Steven and took his face in her hands. "How you doing, honey?" she asked. Steven caught his breath and told her that he was fine, and then the juice-smeared grin plastered across his face told her that he was actually doing much better than fine. "Do you trust me?" Mary asked and Steven nodded "Yes." Mary smiled and then handed Steven her sweaty uniform. "Put it on," she commanded. Steven felt a bit silly, but also ready to burst out in joy. He was all grins as he noticed that Melissa and Melody, and Tiffany and Jancey had paired off and were licking each other like some lesbian sideshow. Melissa came forward with a tube of lipstick. "Close your eyes," she commanded. The lipstick felt so sensual. The only thing that felt better was the feeling of Mary's thickly-painted lips rubbing up against his, and soon she had forced his head back and was darting her tongue in and out of Steven's mouth. And then a deep voice froze Steven in his tracks. "Well, what do we have here?" It was the voice from the bathroom, and Steven turned to find the Janitor standing there leering at the girls. "Six pretty girls. Looks to me like they're only missing one thing. A big fat cock and two balls that are overflowing with my love juice." With that, the janitor dropped his pants and a huge mound of meat sprang upward. It was as big as anything that Steven had ever seen in any of the porno magazines that he had stolen from his sister. That cock was certainly many times bigger than the teeny peenie that Steven had trapped in his panties. And that massive cock was pointed right at Steven. Mary put her arm around him and explained. "Steven, meet Mr. Jones. He's got the best cock in school, but the problem is that he only likes boys." "What a shame," Melody added from the background. "So we're going to play a little trick on Mr. Jones." "Yeah, trick me baby!" Mr. Jones commanded. Steven started to stammer and protest as Mary pushed him to his knees. "Don't worry," she said, "You're not ready to take his monster, but I am." "Me too," "Me Three," "and me" added the other girls. Mary continued her instructions. "We've found that if a little sissy boy will lick his penis, he gets real hard, just the way we like him. And he can stay hard enough to fuck us all, just as long as the sissy boy keeps licking his balls while he fucks us." "What do you say?" Mary asked, and she seemed genuinely ready to accept his decision. "Please Steven, I need it so bad." Jancey pleaded and started kissing his neck. All the girls crowded around, pleading for his help and planting kisses all over his body. But Steven knew that if he licked this man's cock then he would really be gay. From now on and forever. And that was just too much, especially when he looked at Mr. Jones' cock. How could anybody ever get that much meat into them? And Oh Shit! Steven suddenly realized that the monster hanging two inches away from his face wasn't even fully hard yet. He lowered his eyes in shame. He just couldn't do it. He would have to tell the girls "no" and risk the consequences later. But as he looked down he saw a sexy bra and he could almost imagine tiny, budding breasts swelling to fill the cups. His belly was flat, and while there was an obvious bulge in his panties, it didn't detract from the illusion that he was now a girl. And a girl sucking on a cock wasn't gay. In fact, a girl sucking on a man's cock was really hot, and it was making him hot just thinking about it. He lifted his face to Mary and took the step that would change his life forever. "Okay, but I want a girls name first, so you don't think I'm gay" he said and then sank to his knees and began enthusiastically kissing Mr. Jones' penis. All five girls clapped in glee, and Steven was quickly renamed Stephanie. So Stephanie started to give the first blowjob of her new life She tried to take the cock into her mouth, but it was far too big. She finally gave up, gasping in breath and looked up at the janitor to apologize. "Don't worry about it, Stephanie" he said. "You'll learn how soon enough." With that he growled and turned to Melody, threw her over the back of a bench and slammed into her from behind. Stephanie scooted in underneath them and tried to catch the heavy balls as they slapped up against her face and Melody's cunt. She never caught them, but she did lick up all the juice that poured out of Melody when she came. Jancey was next, and this time Stephanie found herself sucking on Jancey's and Mr. Jones' nipples. But she only had one mouth and two hands, so Melissa crept up beside her and soon they were alternating between Jancey's tits and Mr. Jones' nipples. Jancey moaned out as orgasm overtook her. Melissa bent down to French kiss Jancey, and Stephanie slid down to lick up her pussy juices. Mr. Jones' sticky cock prodded against her face, and Stephanie turned to give it a good tongue bath as well. This time she swallowed almost half of it, which got the janitor all worked up again, and he tore away and threw Mary down and started to violently fuck her. Mary had her orgasm even before Stephanie could get there to lick it up. She got to her pussy just as Jones started to cum. He pulled out of her and shot thick streams of cum all across Mary's abdomen and tits. Without even being told to do so, Stephanie licked it all up. It wasn't gay, Steven told himself from somewhere in the back of his mind. Girls like cum. And I'm going to be the best girl ever! Mr. Jones was getting hard again just watching Stephanie. "Damn girl," he said, "I knew when I saw you wearing those pretty panties in the bathroom that you would be something special, but God damn girl..." He didn't finish his thought because Stephanie attacked his cock, and as it was less than full mast, she managed to swallow it all the way to the base. The girls were in shock. Stephanie had just done what most of them could not do. This time it was Mary who bent down and started licking the man's balls. Stephanie's eyes bulged out when he felt the penis start to expand again, but she willed herself to relax and found that she was able to deep throat the cock. The girls gathered 'round and started clapping, saying "Go Girl!" Stephanie was so proud that she didn't realize until it was too late that her mouth and throat were being filled-to-overflowing with cum. She lost her breath and choked, coughing sticky semen up through her nose. As she lay trying to regain her composure, all the girls were patting her on the back and asking if she was okay. All Stephanie could think about was that she had missed some spunk and that she needed to suck it all down before it got cold. Stephanie smiled and went back to work as the girl's cheered her on. As she licked up the spilled cum, Mary dropped down further. Ripping a hole in Stephanie's pantyhose and pushing her panties aside, she engulfed Stephanie's penis to the hilt. Mary had obviously done this before, and Steven came within seconds. Without swallowing, Mary came up and started French kissing her new girlfriend. Stephanie could taste her semen as it coated their tongues. They groped at each other and made out until Tiffany cautioned that the practice was over and they had to clean up before the other cheerleaders came into the locker room. So it was one last cum-drenched kiss and then all six girls jumped into the shower while Mr. Jones started mopping up the locker room. Later that night as Steven lay in his bed unable to sleep, he decided to call Mary. She had a private line in her room, and had said that it was okay to call at anytime. She had written the new number on his penis personally. So at 2:00am, they found themselves talking softly on the phone. "Are you wearing the nightgown I gave you?" Mary asked. "Plus your sticky panties and my sister's bra" Steven answered. "What about the dildo?" "I had it in for almost a half hour, but then it hurt too much and I had to take it out," he replied with shame in his voice. "That's okay sweetie. You keep practicing on it until you can go all night with that baby lodged in your sissy pussy. Take as much time as you need," she said. "I can't take too long," he replied, "I don't think that Mr. Jones will wait much longer for my ass to get stretched out." They both giggled like naughty little schoolgirls. "Well, I guess we'll find out in Friday," Mary finally said. "Why? What's happening on Friday?" "Oh, my parents are out of town so I'm having a slumber party. Just us six girls. But this time we're going to dress you up all the way with a wig and makeup and fingernails--the whole thing. You meet us at the mall at five so we can get your ears pierced. And don't forget, you've got to shave your legs before Friday." Stephanie giggled guiltily "I already did. The hairy legs just felt so icky against the nightgown" "Good girl," Mary said. "Just for that, I give you permission to jerk off, but only if you fuck yourself with the dildo while you're doing it." Stephanie had started masturbating and fucking herself even before Mary finished the sentence. Oh, and Stephanie, just once and then right to bed young lady. You're going to need your strength for Friday." "Why? What else is happening on Friday," Stephanie asked in between gasps of pleasure. "After we get you all dolled up, we've invited the football team over to meet the new cheerleader." In the days that followed the birth of Stephanie at the hands of the five senior cheerleaders (and one well-endowed janitor), Steven's life was radically changed. He had started out as just another one of the unknown sophomores at his high school. Within two weeks he was the cool new kid who hung out with all the cheerleaders. All the boys in school were jealous of this relationship, and all the girls wanted to know just what made Steven so appealing to that select handful of the most popular girls in school. Just what was his secret? If they only knew. Steven was quickly getting used to his role as the senior cheerleader's panty boy. He would arrive at school early and find a soiled pair of panties hanging in his locker. At first, he didn't know for sure which of the cheerleaders had donated today's pair, but after spending a few weeks crouched in between their legs as Stephanie, Steven was quickly getting to the point where he could identify each girl by the smell of her panties. Steven would immediately go to the restroom and put on the panties. Sometimes there would be other "toys" to go along with the feminine finery. Butt plugs were quite common, and they were getting larger and larger as each day passed. There had also been cock-and-ball sheaths and once there was a simple bicycle padlock with a note attached saying "Lock me around those girly-balls of yours." Once Steven was locked in tight, the cheerleaders left the padlock in place for one week straight. It didn't get in the way of his penis, but the hard-steel weight of the padlock as it rested in his panties was a constant reminder that even though he was Steven on the outside, he was really Stephanie on the inside. Every day Steven was given a schedule to follow. Mostly he would go to his classes as usual, squirming to concentrate on his studies while a butt plug stretched him out or a clamps bit into his nipples. After school he would report to the gymnasium, where he had volunteered to be the school mascot. This meant that Steven no longer had to take gym, as he got a P.E. credit by becoming an official member of the cheer squad. That was important, because Steven's entire body below his neck was now completely hairless and his toenails were kept painted a deep red--"Slut Red," Melody had laughed. "Stephanie-Slut Red," Mary had corrected. Previously, Steven had gym for his first period, so he was now able to transfer into a different class. Mary snickered and suggested that he take up art. Now Steven had never thought of himself as the artistic type, but he filled out the paperwork at Mary's insistence. "Trust me," she said, "You're going to love Mr. Mason." The next day Steven transferred into basic art, and was immediately bored by the whole class. Mr. Mason sat him at the back of the room where he found himself daydreaming, anticipating the lunch hour when he would get together with the other cheerleaders. Steven wasn't allowed to eat much, as the girls were helping him develop a more respectable figure. Actually, he never got to eat lunch, but he usually got dessert when they would steal away to a special janitorial closet that Mr. Jones let them use for their lunchtime quickie sessions. Sometimes Mr. Jones would be there waiting for them and Stephanie would get an extra filling meal. Mr. Jones was hung like a horse, and it had taken a while before Stephanie had learned to accommodate him in her boy- pussy. The first time that Mr. Jones fucked him, Mary and Melissa had to hold his hand and help him to keep from crying out in sheer agony. Afterwards Steven felt as if he had been ripped in two, and when he reported to cheerleader practice after school, Mary had found blood in his panties. She had immediately taken him home where she gently rubbed oil into his ravaged backside. She held him in her arms and consoled him. "You'll be fine. All of us take some time getting used to Mr. Jones, and you're doing better than most." She kissed him, being sure to grind her lipstick firmly around his lips. "And besides," she grinned, "once you get used to him, nobody else will do." Steven laughed weakly at the thought. Now that a week had passed, Steven had to agree with Mary's assessment. He had spent the night dreaming wildly about Mr. Jones and "the Bull," as the girls had christened his cock. In his dreams, the bull had found a twin, and so they were free to stuff Stephanie from both ends. It was such bliss dreaming about it that Steven woke with cum spattered all over the inside of his nightgown. The dream had returned night after night, and the cheerleaders decided that Stephanie was having too much fun at night. But even when she was tied down one afternoon and locked into a metal chastity device, she still managed to stain her panties every few nights. Finally Melody gave in and admitted defeat. "That little slut is just too horny," she laughed. "No Wonder she shows up every morning ready to ride the Bull!" Such was the case this morning. Steven woke up and immediately started to think about sex. Mary had pulled him aside before classes started and had him give her a quick licking, but there wasn't enough time to give Stephanie any real pleasure. There wasn't even a butt plug this morning, and so his ass twitched as it yearned to be filled. And now he sat in a boring art class, daydreaming about the Bull and knowing that it would be hours before Stephanie would have her chance to get gored. It was frustrating, and Steven thought of a fun little scenario. He would stand up and scream out, "I want to be a girl full- time. Won't somebody please get over here and fuck me!" And just like that, some fifty high school boys would descend on Stephanie and each of them would be hung like Mr. Jones and spurt gallons of semen with each thrust. It was a delicious fantasy, but unfortunately Steven would have to wait until lunch to get any real relief. The class was working with clay, and Steven decided to pass the time by making a "totem pole," one that was the exact same size and width of Mr. Jones' real life tribute to male virility. He found himself getting excited as he ran his hands up and down the pole, wishing once again that the girls had given him a plug to use today. He felt so empty inside. Class had only been going for fifteen minutes, and Steven came to the realization that he wouldn't be able to make it through the whole period without getting some relief. He raised his hand and asked to be allowed to use the restroom. Mr. Mason didn't seem to care, and Steven was soon running through the halls in search of the maintenance office. He burst in and found Mr. Jones working on something electrical. He was surprised when Steven burst through the door, as this was his private area and students weren't allowed entrance. But he smiled when he saw that it was Steven. The bull liked Steven better than Stephanie, and always knew that it was a hot young boy hiding underneath those frilly panties that he wore. Still, rules were rules, and so the janitor started to warn the student about having to be discrete during the day. The boy just growled at him with a hunger-laden voice. "Shut up and fuck me!" he said and was out of his pants even before he had locked the door. "I've only got a few minutes, so do me hard and fast." Jones barely had time to get up from his stool before ten teenaged fingers were ripping his pants open. He gasped at the heat that burned his cock as Steven swallowed it whole in one quick swoop. Tiny muscles in the boy's throat came alive and quickly coaxed the bull into coming out to play. Now it was the bull's turn to give off heat, as blood rushed in and engorged the organ. As per the little vixen's request, the Janitor picked the boy up as if he were a rag doll and slammed him down across the stool. Steven was already holding his ass cheeks apart, so with nothing more than a well-aimed dollop of spit, the bull charged in and was greeted by the Steven's hot little love tunnel. God, this kid was hot. A few weeks ago he was some nobody-sophomore. Now he was the best fuck that Jones had ever had, and that included some transvestite hookers who made their living by being a hot piece of ass. Steven, or Stephanie, or whatever the cheer-sluts were calling him this week, this kid was amazing because he oozed raw, feral sexuality. He was a natural-born cocksucker, and his ass was so tight. The Bull roared and Steven mewed in pleasure as he was filled up with the janitor's semen. "Now," Jones panted, "go clean yourself up and then get back to class." "If you don't mind," the little minx replied, "I'm going to leave it all inside me so I can feel it dripping down my legs all morning long." Then Steven pulled up his panties, blew the janitor a kiss and practically skipped out the door. Art class was much easier to take now that Stephanie's sexual hunger had been sated. Steven even got into the spirit of the class and started to mold a figure of a cheerleader. He gave the statue a tiny waist, huge breasts, and plump ass and hair that went half way down her back. The details weren't very good, but Steven wished that whatever gods were out there would turn this day into an episode of "The Twilight Zone" and suddenly turn him into the girl he had sculpted. Stephanie was getting worked up again, and by the time the bell rang, she was wondering if there might not be time for a quick visit back to the janitor's office. Steven smiled as he relived this morning's quickie. As if on cue, his ass twitched at the memory and Steven felt a dribble of semen dripping down his leg. The memories were a pleasant distraction, and so Steven took a little while to gather his things and was the last one out of the class. But just as he was at the door, Mr. Mason suddenly reached out and clamped an iron grip on his shoulder. "Steven, I think we need to have a little talk before you go." Steven was abruptly pulled out of his memories, but before he could reply, Mr. Mason threw him roughly to the ground. "My supply room! Now!" he growled in a soft voice that was much scarier than it would have been if he had been yelling. Steven scrambled in fear to his feet, but Mr. Mason kicked him back down to his knees as he turned and locked the door. "Crawl!" he barked, and Steven was too frightened to argue. No sooner was he inside the art supply room than Mason lifted him with surprising strength and threw him across a workbench. Steven trembled in fear for his life as the teacher crushed his face against the bench and whispered in his ear in a voice that dripped with malice. "Do you think I don't know what you're up to?" he hissed. "Sitting in the back, making that 'totem pole' and then rubbing it like you were a common whore!" Steven started to protest, but Mason ground his face into the bench. "Don't you dare deny it! I can smell the sex on you." It was at that point when Mason noticed that the wet puddle of semen had soaked through the back of Steven's pants. "What the fuck is this?" Mason dipped his finger in the moisture and brought it to his nose and sniffed. "Why you little whore," he growled. "I've got just the punishment for a slut like you." Mr. Mason quickly produced four handcuffs and had Steven's wrists and ankles locked to the four corners of the workbench within moments. He was bound up expertly, and by the time that Steven thought to struggle, it was already too late. Steven considered screaming for help, but it was if Mr. Mason could read his mind. He produced an inflatable penis gag and shoved it down Steven's throat and buckled it in place. "Is the little slut scared?" asked when he saw tears start to form in Steven's eyes. Steven nodded, hoping to gain some sympathy, but Mason just smiled and said "Good. You should be." Then he pumped the gag up until it felt like Steven's mouth would burst. Mr. Mason pulled a box cutter out of a drawer and brandished it before Steven's terror-filled eyes. Steven thought that he was about to be killed, and was almost relieved when the teacher simply sliced his clothing off of him, leaving him only his flimsy panties for modesty. Mason did however, cut a large hole in the panties where his finger immediately snaked through and into Steven's cum-slick ass. "So you like getting fucked in the ass, do you?" Mason asked as he laughed to himself. "Well I'm sure that we can give you what you want before the day is through." Then Mason strode out of the room and locked the door behind him. All through the next class period Steven struggled to get free, but it was no use. The handcuffs bit into his wrists and ankles, and the awkward position in which he was tied to the workbench had given him a muscle cramp. Still he struggled loudly until finally he heard the door being unlocked. Mason sauntered in and turned on the kiln and a fan that was loud enough to drown out all of Steven's noise. Then he pulled out a leather wrapped crop and slashed it loudly through the air. "This is what happens to bad girls who make too much noise when they should be quiet," he said and then immediately commenced beating Steven's unprotected backside with the crop. It took only a moment before Steven's back, bottom and thighs were criss- crossed with angry red welts. Mason leaned in close and whispered directly into Steven's ear, "Now be quiet, or I'll really give you something to cry about." And then he was gone again, locking the door and leaving Steven alone in the room with a kiln that was quickly making the temperature unbearable. By the time second period ended, Steven had fallen asleep due to physical exhaustion and the now sweltering heat. He awoke to feel cool hands rubbing some sort of ointment into the welts that burned on his ass. Another set of hands worked the ointment into his thighs, and then Jancey snuck into view and gave him a tender kiss on the cheek. "Mason's a bit rough," she whispered, "but I think you'll have fun before the day is over." Just then Mason came into the room. "So, I see you bitches have a new slutty friend," he said. "Well then, let's show her just what happens to sluts in my classroom." On cue, Jancey and Tiffany stepped forward and began undressing the teacher. They began licking and sucking on his nipples while Melody knelt in front of Mr. Mason. She lowered his pants and began sucking on his cock. As soon as he was hard he shoved the three girls away. He came around behind Steven and rammed his erection without fanfare into Steven's still-slick asshole. He wasn't very big, but Steven still winced with every thrust because of the crop marks that lined his ass. "Come here, slut," Mason spat in the general direction of Melody, "suck my balls while I fuck this whore." Melody quickly complied with the teacher's directive, frantically trying to capture his testicles as they continually slapped against Steven's backside. For his part, Mason was like an animal, pistoning rapidly into Steven who was still stretched out and gagged and unable to do anything other than allow Mason to fuck him like a piece of meat. Steven was still terrified by what was going on, but he was unable to deny that the feral nature of this fucking had him turned on even more than he had been this morning in Mr. Jones' office. Suddenly Jancey stepped into view holding the crop. "Oh, Mr. Mason," she taunted," look what I found." She stepped out of view and all three girls started laughing. And then Mason cried out as Jancey began whipping him viciously. If anything, he began fucking Steven harder as Jancey beat him without mercy. Tiffany found a paddle and started spanking Mason's behind while Jancey concentrated on his inner thighs. But it wasn't until Melody finally captured Mason's balls in her mouth and started to bite down and growl that Mason went crazy. The teacher screamed out in a mixture of pain and ecstasy and flooded Steven's bowels with so much semen that it squirted out as he continued to pump into him. Finally he collapsed, spent and gasping for breath while his cock deflated in Steven's ass and the cheerleaders continued to whip him with the crop and the paddle. And then it was over. Mason collected his clothing and left without saying a word. Jancey, Tiffany and Melody also left, but they didn't release Steven from his bondage. When he muffled something into his gag, Jancey turned around and told him, "Don't worry Stephanie. You've got all day to have fun with Mr. Mason. We'll come and get you after school." And so Steven spent the day strapped down against the workbench in the prep space just off of the art classroom. After third period Melissa stopped by and unlocked Steven. She gave him a drink of water and let him work the cramps out of his arms and legs, but then she dragged him down across the workbench and locked him up even tighter than before. Just before lunch, Mr. Mason stopped by and fucked Steven once again. He didn't say a word, but as he left he taped Steven's eyes closed. Moments later, Steven felt the presence of several people in the room. He only heard one boy's voice say "cool!" but he quickly felt three new cocks ravaging his backside. Mason undid the penis gag and allowed Steven to suck his cock while he was being fucked by the three mystery guests. Steven realized that Mason would like it if he bit down a bit as he sucked his cock, and by doing so, was rewarded with a weak trickle of cum dribbling into his mouth. After all four had spurted into Steven, he was unbound and manhandled into the corner. Steven's muscles screamed at their sudden use, and so he was in no condition to fight as he was quickly mummified with several rolls of duct tape. From neck to toe, he was immobilized, with only his ass, genitals and face remaining free from the tightly wrapped tape. He was wrapped so tightly that Steven couldn't bend a single joint at all. So a rope was tied off around his balls and Steven was propped up in a corner, held erect only by his testicles. Sometime later, Mary stopped by to see how Steven was doing. She didn't say a word, but Steven could identify her by her smell, and was comforted by her presence. Mary unbuckled his gag and gave him a drink of water. Steven tried to speak, but Mary silenced him with a deep kiss and then put the gag back on him. As she left him she said, "Have fun. I'll see you after school." Mr. Mason returned moments later. He pulled the tape off of Steven's eyes so that he could see that there were four other men in the room with him. "Gentlemen," Mason began as if he were addressing a distinguished gathering of intellectuals. "I came across this boy-slut earlier today. She already had a load of cum deposited in her ass-pussy by the time I found her, and I added a few spurts myself. Now the question is, what shall we do with her to show her the error of her ways." The first man stepped forward and kissed Steven on the cheek. "My dear," he said, "I think the chair would do you some good." One by one, the three other men came up and repeated the same sentence. "So the chair it is," Mason smiled and pulled Steven toward him by the rope wrapped around his balls. The tape was quickly ripped off of Steven's body, taking a good deal of skin with it. The four men took turns holding Steven tightly while they fucked him, one-by-one, until Steven could no longer feel them as they thrust into his ass. No sooner had one man spurt his semen than he came around to Steven's front and forced Steven to lick his cock clean while the next man mounted him from behind. When all four had cum, Steven was dragged into a back closet. Inside there was a wooden framed chair with a large pole jutting out of the seat. Steven had been fucked so much that morning and was so stretched out that it was no problem at all to lower him down onto the pole. Leather buckles were quickly secured around his arms, legs, chest and head, and then he was ungagged only long enough for a long rubber phallus to be slid into his mouth. It bent Steven's head up at an awkward angle, which allowed the fake cock a straight shot into his mouth and down his throat. Two clamps were attached to Steven's nipples and pulled taught, and then a leather strap was wrapped around his testicles. It too was pulled tightly away from his body. Steven sat there unable to move a muscle. He had a pole rammed up his ass and a dildo crammed down his throat. His nipples and testicles were being pulled cruely away from his body, and still he managed to sport an erection. Mr. Mason noticed that the little sissy was erect. "Well slut," he said, "Let's see if you're still as excited after a couple of hours in the chair." And then he attached a pair of headphones to Steven's ears and closed the door to the closet. No sooner had the door locked closed than the chair sprung to life. The pole stuck up into Steven's ass began to pump up and down, expanding in girth as it went. The same held true for the dildo that assaulted Steven's mouth. The only difference was that every fifteen minutes or so the dildo spurted a concoction that tasted remarkable like a man's cum, and it ejaculated so much of the substance that it overflowed Steven's mouth and ran down his chin and splashed on his chest. But the worst pain of all was located in his nipples and balls. They were pulled so tightly away from his body that Steven feared that the chair might do permanent damage to his more delicate areas. Steven could barely hear the school bell ring and he was aware of the general sound of students leaving for the day. It seemed like an eternity passed while he sat impaled on the chair, wondering if he had been forgotten. Then he began to hear hushed voices approaching. There were two men coming. One was scared, the other was pretty angry. The door flew open and the angry voice cried out, "Motherfucker, Mason, I warned you to knock this shit off." It was Mr. Jones, and he towered over Mason in rage. "Get ready, mother," he spat, I'll deal with you next. Mr. Jones carefully untied Steven and helped him out of the chair. He had a flask in his back pocket and gave Steven a small sip while he gathered his strength. By this time Mason was naked, and shaking as he wondered about his fate. Mt Jones wasted no time in picking the teacher up and slamming him down onto the chair. He tightened all the straps down tight and started the fucking machine portion of the contraption into motion. A wicked gleam came into his eyes. Mr. Jones left, but came back a few moments later with his lunchbox. He opened it and handed Steven a warm Coke. Then he took out a bottle of hot sauce and began rubbing it into Mason's cock. The pain must have been overpowering as tears poured out of Mason's eyes. The smell was overwhelming in the confined space, especially when Mason shot his load so hard that it nearly hit the ceiling. Then Mr. Jones went to one of the lab sinks and yanked hard on one of the pipes. It sprang a leak and started to flood the backroom. "Well fuck," the Janitor growled, "looks like I'm gonna have to close this room down for a few days while I fix the plumbing. I should be able to get students back in here by Friday, but don't expect me to release you before Monday." Mason moaned as he knew that he would be spending that whole time being punished for his assault on Steven. For his part, Mr. Jones just stood menacing over the art teacher, trying to think of the best way to make him pay. That was when he felt a soft pair of hands wrapped around his legs and slowly squeezing up toward his cock. Jones looked down and saw the naked boy looking up at him. "My hero," he said as he unzipped the janitor's pants. Steven was still too sore to move much, but he needed to give his rescuer a reward. Mr. Jones was leaning back against the wall while Steven devoured his cock when the cheerleaders made their way into the room. "So what's going on here," Mary asked as the girls entered. They all quieted down as they surveyed the scene. No one said anything for a few moments while Steven finished giving his reward. Then the girls helped him to his feet, and finding a blanket in a closet, helped the naked boy into the gym locker. Steven sat under the hot shower spray and cried. Mary and the girls had stripped down and held him. Pretty soon they were all crying. Steven cried from the physical pain, but he also cried because he was scared that he liked it so much. He cried that he was just a dumb kid, and while the girls were his friends, he cried because he knew now that he would never fully be one of their gang. Mr. Jones found some clothes and helped Steven get dressed. Then he drove everybody back to Mary's house. The girls helped Steven into a nightgown and put her to sleep in Mary's bed. They called the football players and explained that the party would have to wait. When some of the players started to complain, Mary shut it down quickly with an icy tone that left little doubt that they would respect her command or else they would never see any action from any girl in school, ever again. Mary called Steven's mother and said that they were having a cheerleading party, and the needed their mascot to help with some stuff. "Not to worry," she lied, "Stevie can crash in my brother's old room." Mom didn't really buy it, so Mary eventually gave in and told her what was going on. Naturally she freaked out and drove right over, but calmed down when she saw her little angel sleeping so peacefully in her pink nightie. She started to cry. Then the girls all started to cry. They cried until late in the night. And so it was that all five girls spent the night sleeping in a huddle around Steven while his mom crashed in the room next door. She slept soundly knowing that the cheerleaders would protect her baby. After some much needed sleep and a good breakfast in bed, the girls all made their way down to the living room. Mom and Mr. Jones were waiting for them as the filed down the stairs. He stood and offered Steven a bunch of flowers as he asked, "how ya doing, honey?" Steven smiled a little and crawled into Mr. Jones' lap while the group discussed Mason's fate. They could get him fired. They could blackmail him for the rest of his life. Jones even knew a few "serious brothers" who could make him disappear forever. They talked all morning and eventually came up with a plan. Sometime after midday they made their way to the classroom back prep space. Mason was still there, strapped to the chair and moaning. There were two men who had spent the entire night rubbing him down with hot sauce, and his cock looked like it might never recover from the torture. Steven stood in front of Mason and slapped him until he had his attention. He removed the gag and Mason started to cry and beg for forgiveness, but Steven slapped him again and again until he quieted down. "Okay, here's the deal," Steven spat out with a new-found authority. "We've spent this entire time thinking about how to punish you, but I have a better plan. You're gonna help me instead." Mason gawked up, not understanding. "I like being a girl." He looked over at his mother, saying "I want to be Stephanie for real. But there's no way I can afford that, but you can." And so the deal was struck. Mason agreed to confess to everything on a video camera, which mom would then keep locked up tight in a safety deposit box. He would quit his job and move out of the city, promising to never teach again. Every month he would get a bill for Stephanie's medical bills. She would start getting the best hormone treatments and plastic surgeries until she could pass as the perfect high school girl. When it came time for the final sex change operation, Mason would pay to send the whole group for a month long vacation to Thailand to help Stephanie recover fully. The final punishment was a solid steel chastity belt which Mr. Jones glued around Mason's cock and balls when he finally released him from the chair. Mason was so numb that he didn't even feel the device being locked into place. One year later, Stephanie and her friends all came home from Thailand just as college was about to start. The school district had heard some rumors of Mason's activities, and fearing a lawsuit, they allowed Steven, now Stephanie full time, to finish her studies up at home. The girls all went to the same school--bonded by their love for Stephanie. As frequently happens, the girls drifted apart a bit as they eventually pursued their own interests and boyfriends. But they were all there five years later on Stephanie's big day. She looked drop-deal gorgeous in her wedding dress. It was top of the line, but money was of no concern, as Mason was paying for the whole thing. Mother beamed as she watched her daughter walk down the aisle. She was so happy that her baby boy had grown up to be such a strong young woman, and knew that was because she was surrounded by her loving posse of friends. Tears welled up when she heard Stephanie say "I do," before leaning in to kiss the handsome janitor. Well former janitor, as he had used some of Mason's seed money to start his own janitorial business. Stephanie was already working for him while she finished her degree. Well, maybe not actually working, she thought as she imagined how her daughter might be spending her afternoons with her husband behind closed doors.

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Panty raider to slave boy. A fantasy of women using a man. Part oneBob was a first year at college and wanted to join the fraternity zeta beta and had been accepted eventually to undergo initiation into the fraternity. Many had been turned down by the seniors and the last test to get as far as being allowed to pledge had embarrassed Bob as he had to strip naked and run around a football pitch and then rub himself hard while the seniors laughed at him and the other lads many of whom had either...

2 years ago
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HOW TO DETERMINE IF YOU ARE A PANTY BOY

If you do not share in this particular fetish, which is to wear panties, I suggest you search for a more appropriate story. This little epistle has nothing erotic in it besides the discussion of our “boys” that love to wear panties.In my my long held opinion, based on nearly 60 years of wearing panties, that this is how we should define what is known as a panty boy. If you disagree with my opinions please feel free to comment regardless of how long you have been defining yourself by your desire...

3 years ago
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Samanthas Panty Boy

Waking up to the smell of bacon and eggs I looked at the clock flashing 7:30AM and for a second thought I was going to be late for work. Remembering it was Saturday morning I got up, put on my robe and walked to the kitchen. My beautiful wife Samantha was already awake, had taken a shower, and was dressed to kill. She was standing at the stove with her pink lacy apron on cooking the bacon and eggs that had woke me up. She greeted me saying, "Good morning Jack," as my eyes adjusted to the light...

3 years ago
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Cheerleaders 2

God, he thought, i’ve just sucked my sister’s pussy. What have i done? As he sat there in shock, jamie reached down and stroked her own pussy, rubbing her clit fiercely as she sat up. “god, that was wonderful, james,” she said, her eyes glistening. “thank you so much.” “jamie, this isn’t right,” james protested, overcome with guilt at what they had done. “we shouldn’t be doing this.” “i know, but we’re not doing anything really wrong. I mean, nothing can happen from this, can it?” “no, but –”...

Incest
3 years ago
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Claire Kent Alias SuperSister The Return of Superboy

When a vengeful woman turned the teenage Clark Kent aka Superboy into Claire Kent aka Super-Sister, that was the last anyone ever saw of Clark, or so Supergirl believed. So why, when she travels back in time from a period when her now adult cousin is the world-famous Superwoman, does she find a Smallville in which Superboy is back, and Claire Kent is one of the town's bad girls? CLAIRE KENT, ALIAS SUPER-SISTER: THE RETURN OF SUPERBOY by BobH (c) 2006 All characters herein...

2 years ago
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Panty Boy

“Timmy, dear” Cassandra said while reading morning paper at the breakfast table, “I have a convention in New Orleans and I’m leaving right after work for the airport, so I’ll have the cabby swing by here and pick up my bags!!!” “I’ve laid out all the clothes I’m going to need, but I want you to get them all packed and ready to go, understand!?!” “How long are you going to be gone,” the crest fallen young man asked sadly?!?...

4 years ago
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It Isnt Easy Being a Panty Boy

This is another fantasy piece with bits of my past in it (no I won’t tell which parts). Hope you enjoy, this is a FETISH story about cross dressing in panties so if that is not for you keep searching.“It isn’t easy being a panty boy,” I thought to myself as Ann, my coworker in my office cube said, “are you wearing blue silky panties Larry?” I immediately realized my shirt had pulled out of my trousers as I bent to add paper to the printer. I didn’t answer her question but I am sure my red face...

3 years ago
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The Panty Boy

It was a rainy summer, a long time ago, and it was my birthday on that day, so we decided to party in my place, and entertain my buddies, and have a good time.  As I was there in my apartment, guests began to arrive, unhurried, though. Perhaps this would be a good gathering, until last guest arrived. She was my girl friend named Blanca Guerrero, a Spanish, dressed elegantly in black tight pants and a blouse with horizontal stripes on it.  She looked stunningly gorgeous like this! I wished I...

Fetish
3 years ago
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Calling All Panty Boys

This is a totally made up story with a picture of one of my friends here on XH, wonder if he will recognize himself. I love panties and so does he so we will celebrate with this little fantasy. I will mark it gay because every time I mark something shemale the critics give it a thumbs down.I felt her hand slide in my pants and rub his fingers across my panty covered cock. I can’t tell you exactly how this happened. I just know that lying in the dark with her fondling my hard cock that was...

4 years ago
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Black Mans White Pussyboy

Black Man’s White Pussyboy Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog. I let Jay into the apartment. He was looking for a one bedroom, furnished place and had called about my ad in the newspaper. I hoped to rent this place quickly, then I would be full and could devote my time to some maintenance and repairs rather than showing places. I looked at...

2 years ago
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  • 91
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Black Mans White Pussyboy

Black Man's White PussyboyStory from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.I let Jay into the apartment. He was looking for a one bedroom,furnished place and had called about my ad in the newspaper. I hoped torent this place quickly, then I would be full and could devote my time tosome maintenance and repairs rather than showing places. I looked at...

4 years ago
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  • 86
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Black Mans White Pussyboy

Black Man's White PussyboyStory from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.I let Jay into the apartment. He was looking for a one bedroom,furnished place and had called about my ad in the newspaper. I hoped torent this place quickly, then I would be full and could devote my time tosome maintenance and repairs rather than showing places. I looked at...

1 year ago
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  • 96
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Black Mans White Pussyboy

Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.I let Jay into the apartment. He was looking for a one bedroom,furnished place and had called about my ad in the newspaper. I hoped torent this place quickly, then I would be full and could devote my time tosome maintenance and repairs rather than showing places. I looked at therental application he had...

4 years ago
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Black Mans White Pussyboy

I let Jay into the apartment. He was looking for a one bedroom,furnished place and had called about my ad in the newspaper. I hoped torent this place quickly, then I would be full and could devote my time tosome maintenance and repairs rather than showing places. I looked at therental application he had filled out just a minute earlier. From the datelisted as his birth date, he was 22 years old, three years younger than I.I watched him, explaining about the living room area and kitchen, as...

2 years ago
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Panty Boys

By Fred GingermanChapter One - Nerds UnitedMy name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.We were pretty much classic nerds. Shy. Picked on. Ostracized....

4 years ago
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Pantyboy Honeymoon

Pantyboy Honeymoon By Gingerfred Man Chapter One -- The Wedding Day "You have to stop crying, Stacey," Daddy said. "You want to look pretty for Mr. Biggenstiff, don't you? The man's so excited about marrying you, he's practically jumping out of his skin." "But, Daddy," Stacey bawled. "I don't want to marry Mr. Biggenstiff! Or any man. I'm too young. I won't even be 18 until tomorrow. And I'm a boy!" Well. Stacey Wigglebottom was right on both counts. But Daddy...

2 years ago
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cheerleaders trust

Megan bit back a curse as she stubbed her toe. The light from a few lamps in the parking lot filtered lazily through the library windows. As the building had been closed for almost five hours, this glow was all she had to aid her sight. It wasn’t enough. The table that she had walked into was the fourth one of the evening. Her toe was stinging, which probably meant that the nail had broken. Still, she shuffled forward. ‘Hello?’ she called. ‘Is anybody there? Casey?’ She sucked in her breath...

2 years ago
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cheerleaders trust

Megan bit back a curse as she stubbed her toe. The light from a few lamps in theparking lot filtered lazily through the library windows. As the building had beenclosed for almost five hours, this glow was all she had to aid her sight. It wasn'tenough. The table that she had walked into was the fourth one of the evening.Her toe was stinging, which probably meant that the nail had broken. Still, sheshuffled forward."Hello?" she called. "Is anybody there? Casey?"She sucked in her breath at the...

2 years ago
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Cheerleaders are very Practical

College cheer leader Sammie believes she has no option but to take on two judges at once to make sure her team wins the regionals.... Samantha, Sammie Green, always got what she wanted. Always had. Always will. Right now she wanted to win, even more than trying to get inside her new team mate, cute Morgan’s bra and licking her unknown mystery arsehole, some good things you had to work a little bit for, but Sammie was confident of Morgan’s lush titties being all hers as she grabbed her fetching...

4 years ago
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Cheerleaders Never CryChapter 2

Sue was pleased that her Uncle Donald had taken her virgin ass on a test drive the previous night when her parents were not at home. She kept his stuff inside her the entire night hoping it would not leak out and stain the sheets with incriminating evidence. There was no doubt in her mind that the older man regretted his impetuous humping of her rear door and she was smiling in his direction more than usual just to reassure him that she would keep her mouth shut and was grateful for his...

2 years ago
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Black Knight Takes White Pawn Pussyboy

Black Knight Takes White Pawn Pussyboy Story from the perspective of a white teen pussyboy who becomes the sex slave of a couple niggers who use him for gang bangs and fuck films.I first met Arnim, my future nigger buck master, when we both worked for a well-known department store in London: in the packing and returns department at the rear of the building. Mr. Potter, the person in charge of the department, was a hard man to please. He was ex-army and arrived for work each morning dressed in a...

4 years ago
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Cheerleaders And The Shower

Cheryl had been my best friend since I joined the cheerleading squad at State College. We would go to the mall together, watch movies together, and study together, you know, just about everything. Cheryl was about 5’9″ (I was a wee bit shorter), and had a figure that bespoke ‘Modeling Career Here’. I’ll admit that I wasn’t nearly as attractive, but the guys I dated never seemed to think so. Anyway, Cheryl really surprised me one night after an exciting...

3 years ago
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pantyboy

Another month passed since Steve got his promotion and we had any time away from the k**s. That previous night alone was another memorable one in which I bought him a nice black pair of thigh highs and a black lacy garter belt that matched his black satin bikini panties. He was so aroused he came in his panties as I rubbed his crotch on the drive home from dinner. The rest of the night was memorable as well because Steve had described different panties and pieces of lingerie that he had...

4 years ago
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sisters pantys draw

ever since i started wanking i had a panty fetish. at first it started innocently with picture of bras and pantys but soon my curiosity got the better of me. one day when in the house all alone i found myself in my sister bedroom pretending to myself that i was in there looking for something of mine however i knew what i was there for get closer and closer to her panties i could feel my cock twitching in my pants and growing hard in excitement before i had even i opened the draw. then there i...

2 years ago
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Mr Boyd

My first day at my new job was coming to an end when my boss called me into his luxurious office to have a word with me. I didn’t know what it was about, but I felt confident that I had gotten off to a good start with all my responsibilities.“Hey, I just wanted a quick word with you,” he said, looking up at me with his handsome smile from his chair.“Sure,” I said, sitting down in one of the two chairs in front of his desk.He slightly raised his right hand off the desk and said, “Carol, I know...

Cheating
1 year ago
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Hello LadyBoy

How many of you get off to fucking ladyboys? Well, if you know what I’m talking about, then you know precisely the kind of sexy people I’m referring to. But for those whose brains are melting at the term of ladyboys, let’s keep it simple for them. A ladyboy is an Asian transsexual. But then again, if you didn’t know that, you probably are not into this kind of porn in the first place!On the other hand, if you are or are curious, allow me to invite you to Hello Ladyboy. This series has been a...

Premium Shemale Porn Sites
4 years ago
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Cheerleaders Fun and Games Chapters 34

Chapter Three The girls were all huddled close together under the blanket when I came downstairs. "Hello my pets." The girl Emily started whimpering, and Tara stood up screaming. "What are you doing to us? Where is Monique, you can't keep us like this!" "You're right Tara, I have such better plans for you. Look at all this empty space." I spread my arms to the 1500 sq ft of unfinished basement. "You are all now my slaves, and I'm going to build my own little dungeon to house you, just be...

1 year ago
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Cheerleaders Never CryChapter 3

Pretty teenaged cheerleader Sue was not quite as innocent as she looked and pretended to be to her parents and most of her friends. In fact, she was in the “Virgin until married” club at her local church and the Pastor was convinced she had never been touched below the waistline. Now that her convicted but paroled uncle Donald had been sponsored by her parents and housed in the basement, she had plenty of opportunity to have him tutor her on the deviant practices he had employed in a way...

1 year ago
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When I was a busboy

This happened many years ago. I got a job working as a busboy.This was a very classy restaurant and I was almost getting used to talking to customers. Some customers were kind of snippy, but some were also very nice. This story is about what happened on a week night. The place was kind of busy but not slammed like it would be on a Friday or Saturday.I had just watered the tables (poured water into empty or mostly empty glasses). I had had left, after watering a table with an older couple...

4 years ago
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  • 75
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Tyrones Crossdressing White Pussyboy

Submissive whiteboi becomes a sissy faggot pussyboy for his nigger master.It was to be a night of romance. My Nigger lover, Tyrone, gruntedas he pulled his glistening cock from my aching, cum filled asscunt. Hehad just shot a massive load of man slop into my steamy, grippingentrails. Our lovemaking had been a brutal affair, as it always is, which is just the way I like it. I am a subjugated fuck slave, nothing but a sissy faggot sperm receptacle for my dominant nigger lover.Tyrone is the envy...

4 years ago
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  • 27
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Daddys Panty boy

The first inkling that something interesting was happening between dad and me came about because of my taking up running for exercise. My dad was a big guy, about 6'3 and well over 200 pounds, so I'd always been worried that I'd get a gut like he had. It looked fine on him, with his height it was proportional, but I was just 5'10, I didn't want a belly. One day when I got home from my classes I just started running. That night at dinner my dad asked how I liked it."It was okay except my balls...

3 years ago
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The Making of a Houseboy

Hilde patted the edges of her mouth with the linen napkin. Looking to her husband, he smiled and placed his cutlery in a perfect line on his empty plate.“Very good, you have certainly passed this aspect of the interview with flying colours.”Graciously, I nodded my head, “You are welcome, I like cooking, even more so for other people.”Noticing their wine glasses were a quarter full, I scuttled around the table to charge them. I topped up their water glasses too.“Would you like the cheese board...

Bisexual
2 years ago
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The Houseboy

If I had been told on my sixteenth birthday, that I would end up working as a houseboy, I would’ve advised the forecaster of that statement to sign up for some psychological evaluation. That, however, is exactly what happened by the time I had turned seventeen-years-old.To fully explain how this came about, I am afraid that I now have to embark on a two-part history lesson:Firstly, after my mother had left my dad and me when I was eight-years-old, my father continued to be employed as a foreman...

Gay Male
4 years ago
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  • 75
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The Quest for the Black QipaoChapter 2 Harry The Houseboy

Harry’s life as a Phyllis’s houseboy had turned out to be better than the situation of many of his contemporaries. A sponsored male in New Order Britain wasn’t under the sort of constant surveillance, harassment, and suspicion of subversion that un-sponsored males had to put up with. And besides, Phyllis had turned out to be a reasonable sponsor. The dream at school had been to be picked out as some girl’s life-partner but, realistically, that didn’t happen to more than a handful of men....

4 years ago
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  • 75
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Denise Femboy

Brief story summary: Mummy feminises son Denis(e) from birth. She, Denise, was born with a penis but in spite of that, she has always been a little girl like her two slightly older sisters. Mummy was/is a great believer in Strict/Extreme Corporal Punishment in Disciplining her c***dren and does so on a regular basis with the help of her pharmacist friend Mrs Nugent. All punishments however are lovingly although not sparingly applied and are implemented solely for the c***dren’s own good. That...

3 years ago
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  • 73
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Denise Femboy

Brief story summary: Mummy feminises son Denis(e) from birth. She, Denise, was born with a penis but in spite of that, she has always been a little girl like her two slightly older sisters. Mummy was/is a great believer in Strict/Extreme Corporal Punishment in Disciplining her c***dren and does so on a regular basis with the help of her pharmacist friend Mrs Nugent. All punishments however are lovingly although not sparingly applied and are implemented solely for the c***dren’s own good. That...

2 years ago
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  • 21
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My Paperboy

The Paperboy Isn't a Boy Anymore It was 10:00 A.M. when I looked out the door to make sure my tiny back yard was empty and there was no one in the alley behind my house. All clear. I popped out the door onto the back porch. I was naked, carrying an armload of potted plants to put on the porch railing. I often spend time around the house naked. I like it that way. Going in and out doors sometimes giving a free peek is part of the fun. Tires screeched and a horn blew three times in the alley....

3 years ago
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American Ladyboy

American Ladyboy By Cassandra Morgan No matter where in the world you are, no matter languages are being spoken around you, calculus is boring, it seems they teach the subject so people will know how to torture spies. And so, half a globe away, Benjy Hawkins sat in his math class with his head resting on his arms, which were folded over his desk. The teacher droned on, his lilting accent punctuating his speech. The subject, and the speech, was more than Benjy could bear on a...

3 years ago
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Pussyboy

Pussyboy, Part 1By Greg Stone Part 1Greg peered over the menu to check out the young waiter working the lunch tables. He'd wanted to avoid the noise of the business lunch crowd on a Friday, so he was at this trendy little place filled mostly with students. The menu didn't interest him, but the fair-haired young man breezing between the tables did.He looked about twenty, with a small build and rather effeminate mannerisms. The highly styled hair and close-fitting clothes suggested a...

4 years ago
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Husband Wife and Schoolboys

THE HUSBAND, THE WIFE AND THE SCHOOLBOYSPart OneLet me explain. My name is Justin. I am a healthylooking 40-year-old married guy and in quite good shape. Not film star shape but I can still pull acompliment or two. I was lucky to marry an extremelypretty, little women called Carrie. She is still 30and we have been married for 10 years so you haveprobably guessed that she was 20 when we married. Iwas lucky, O.K? She has certainly stayed in shape andher slim body pert little upturned breasts and...

3 years ago
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Cheerleaders Fun and Games Chapter 5

Chapter Five I woke up with Monique in my arms. I could feel her body tense against mine as I moved, and I wondered if she'd got any sleep at all during the night? I'd slept wonderfully, I didn't wake up once. I'd thought for sure I'd have needed to cum, but it hadn't worked out that way. "Good morning slave." I brushed the hair out of her eyes. "Are you disappointed I didn't fuck you in the night?" Monique remained silent, I could sense the incredible disdain she was feeling and I thrust my...

4 years ago
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Cheerleaders Fun and Games Chapter 2

Chapter Two I couldn't believe how rested I felt in the morning. I found my cheek pressed into Monique's breast. I was a little surprised to find her sleeping, breathing softly, seemingly contented. I eased out of the bed and headed for the bathroom. I could already feel the aching in my loins, I knew I needed to fuck her again, bad. When I got out of the shower and headed back into the bedroom I could see Monique's eyes flutter open. It was 10am, I couldn't' believe I'd slept so long, but it...

4 years ago
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Two Pantyhosed Guys I wrote this over 15 years a

Title: Pantyhose Guys Part1 I had first contact with a fellow pantyhose wearer through the chat room. I was just looking around watching the conversations develop, stroking my nylon encased thighs, adding a comment here and there when a new person entered the chat room. ‘Hi, I am rather new to all this. I love to wear pantyhose as often as I can and was wondering if there are any guys here who would like to meet in real life?’ This looked too good to be true as I had been thinking about...

3 years ago
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Two Pantyhosed Guys I wrote this over 15 years a

Title: Pantyhose Guys Part1I had first contact with a fellow pantyhose wearer through the chat room. I was just looking around watching the conversations develop, stroking my nylon encased thighs, adding a comment here and there when a new person entered the chat room. "Hi, I am rather new to all this. I love to wear pantyhose as often as I can and was wondering if there are any guys here who would like to meet in real life?" This looked too good to be true as I had been thinking about...

4 years ago
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Panty Thief

Panty Thief Chapter 1 Cammy moved as quickly and as quietly as he could along the upstairs hall making his way to the closed door at the end. When he got there he pushed it open with a slight creek of the hinges and then slipped soundlessly into his cousin Giselle's room closing the door with a soft 'click' of the latch. The room was femininely appointed, definitely decorated to suit a teenage girl's tastes, but Cammy barely noticed as the 15-year-old made directly for the long...

4 years ago
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Panty Pride

Panty Pride By Gingerfred Man Chapter One -- Mutual interest All your life, people tell you that you need to find others who share your interests. Common ground. Birds of a feather. Flocking together. Sounds like a good idea, doesn't it? It is. Unless you're so ashamed of your "interest" that the mere act of looking for someone who is like you foreshadows a pit of potentially abject humiliation. Sure, it's no problem if you like to collect Crimean War hand weapons or...

2 years ago
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Panty se Blue Film Tak

Hi this is Pabby… I am a very friendly and loving man of 30+ now, living in Chandigarh. Married/unmarried/ unsatisfied women/couples contact me for a satisfying date. Ladies call me for escort contact me immediately. Secrecy guaranteed and demanded. Only serious people contact me now at Mera naam Roshni hai. Mein southern Delhi mein apne mummy papa ke sath rehti hun. Meri umra 19 saal hai, Gora badan, kaale lambe baal, 5″4 ki hieht aur meri aankhon ka rang bhura hai. Ek din mein apni saheliyon...

3 years ago
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MY MAN AND I SHARE A LADYBOY

My man Roger and I have had sexual adventures that many people would be envious of: some incredulous of even. Around once a month I love having a second man to pleasure me and before I pleasure him while my man watches, and often he will pleasure my man: oral sex only – no intercourse is the rule. In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock. “Some of your...

4 years ago
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The Panty Life

The Panty Life by Gingerfred Man A long time ago, in an era far, far away, there was no place called the Internet for all the pretty pantyboys in the world to meet, communicate and comfort each other. There was no United States Sissy Corps, no sissy-centric country of Gingerfredonia, no Panty Boy magazine or annual Miss Panty Boy competition. There were no sissy milking stations at malls and no Panty Pride gatherings in all towns, great and small. There were no Boy Brides Society...

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