Date: Wed, 22 Jul 2015 21:13:19 +0000 From: Beau Kramer Subject: Sissyboy Apprentice (gay adult-youth) Sissyboy Apprentice (gay adult-youth) By Beautiful Creamer One – The Setup Tommy Darling didn't like the attention Jay Steelpole was giving him that Friday afternoon in sixth-grade English class. Tommy was as straight as a really straight arrow and the word around school was that Jay was gay as a really curved arrow. OK, bad metaphor, but you get the idea. Gay Jay the other kids called him. But Jay didn't seem to mind. It didn't stop Jay from mincing around unmanfully or flirting with some of the male teachers either. Why was Jay giving Tommy the eyeball that day anyway? They had barely spoken to each other since the beginning of school. Not that Tommy had anything against gay people. In his estimation, it was live and let live. As long as all the "gays" were exiled to their own gay island or something. Which would only be fair, since they made people like Tommy, straight people, uncomfortable. Tommy caught Jay staring at him all through class, but then when the bell rang to move on to the last class of the day, Jay didn't even acknowledge Tommy. Odd. Even odder was when Mrs. Orderly, the school secretary stopped Tommy in the hall and told him that his mother would be going out that night and that Tommy would be going to the Steelpoles' home for dinner and a sleepover. A sleepover! With Gay Jay? No way!! Though, apparently, way. "But I don't have my clothes or anything, Mrs. Orderly." "The Steelpoles will take care of that, Tommy." "But I don't even know where they live," "Jay will meet you at the statue in front of the school and you can walk home with him. Doomed! Tommy would be seen with Gay Jay! Word would be out. Tommy's reputation would be toast. Gay toast. Doomed! Two – Boy Meets Boy Jay Steelpole was very excited to get to know Tommy. In Jay's expert appraisal, Tommy was the second prettiest boy at Charles Manson Junior High School. Next to Jay, of course. As such, Tommy was clearly wasting his time pretending he was straight. And depriving the men and boys of their town of his boyish beauty and charm. Not to mention what Jay had noted in gym class looked to be the nicest boy bum he had seen in sometime. Yes, all that stuff about the gay agenda that you've been hearing from Republicans is true. Gay recruiters are roaming the junior highs, looking for straight, innocent victims to pervert into perversions in a perverted "lifestyle choice." Or, maybe, Jay just wanted to see if Tommy liked having a pretty boy like Jay give him some really nice orgasms. Jay believed that he, the master sissyboy of the town of San Spermino, California, would make Tommy Darling his apprentice. Jay's Mom and Daddy were very supportive of Jay's "activities." Daddy, especially, since he was "active" in Jay's "activities." Jay's Mom just wanted her son to have friends his own age. Even if he had to take them to his bed and coax all their sperm out of them to solidify their friendship. Jay's Mom realized that Jay's need to be a sissyboy altered the pattern of his peer relationships. But some of Jay's "special activities" altered the pattern even more. She was hopeful when Jay told her that he thought Tommy had the potential to be Jay's friend. He even called Tommy his "apprentice." How cute! So she was fully cooperative in setting up a surprise sleepover for Tommy and her boy at their house. Tommy's Mom was very cordial about it all. Had she heard the talk about Jay being gay? She had, but who cared? Tommy needed to get out of the house now and then. She needed to get out of the house now and then. Since Jay's no-good father had left, Tommy's Mom had hardly been able to date men. A sleepover for Tommy with Jay would be a win for Jay and a win for Tommy's Mom. Too bad for Tommy. Which described Tommy's mood perfectly as he waited for Jay at the statue in front of school. Tommy prayed that Jay would be late. Showing up after all the other kids had left the school grounds. Or, even better, not show up at all. Tommy and Jay had nothing in common so it just wasn't fair that... Oh no! It was Jay. Walking straight for Tommy. Actually, walking "straight" was a poor description for Jay. There was nothing "straight" about the way Jay walked. Was anyone looking at Tommy as Jay approached Tommy wearing a big smile? PLEASE don't let Jay HUG Tommy or something! In public! Whew! Jay didn't hug Tommy. But he did extend a hand for Tommy to take so that they could walk to Jay's house hand-in-hand. Which Tommy refused! And tried to pretend that, although Tommy and Jay were headed in the same direction, they weren't walking together. Which made Jay chuckle to himself. Since the pretty sissyboy was all but certain that within 12 hours or less, Tommy would be sucking Jay's cock and swallowing Jay's sperm. Jay was sure that Tommy wanted "it." The sissyboy-to-be just didn't know it yet. The boys walked without conversing and arrived at Jay's home 15 minutes later. Jay's Mom was warm and friendly to Tommy. Which made Tommy wonder how she could be so "normal" when her son was such a "queer." Well, Tommy could tough all this out. Avoid Jay. Watch TV until bedtime, then lock himself in a bathroom, sleep in the tub and avoid anything even vaguely gay. Good plan, huh? It started to fall apart early on when Jay's Mom's was so kind to Tommy. She treated Tommy as if he and Jay were old friends and that Tommy had been at their house for dinner lots of times. She served a tasty meal of fried chicken, mashed potatoes and corn on the cob, with a big ice cream sundae for dessert. So how could Tommy embarrass and disappoint Jay's Mom by running to the bathroom and locking himself in? Jay said little to Tommy during the meal, but he was cordial and helped his Mom do the dishes while Tommy and Jay's Daddy watched a ball game on TV. Normal stuff. Maybe Jay wasn't gay at all. Maybe he was just a little south of completely manly. Maybe Tommy and Jay could become friends. Not besties or anything, but the kind of guy you say hi to in the hallway at school. Tommy was less impressed with Jay's Daddy. The man paid a lot more visual attention to Tommy than he did to the ball game. Was Jay's Daddy "undressing Tommy with his eyes?" It kind of felt like that. Which was creepy. Though Tommy could have just been imagining all that. Anyway, except for the possible weird signals Jay's Daddy was sending out, things seemed pretty normal. So Tommy dropped most of his guard. Mistake? You make the call. Jay joined his Daddy and Tommy to watch the game until around 8:30 p.m., at which time, Jay's Mom told Tommy and Jay that it was time to get dressed for bed. Which was almost normal. Announced by a normal person. Tommy's bedtime on a Friday was usually 10, but getting dressed for bed isn't go-to-sleep time. So he followed Jay's Mom and Jay to Jay's room. Mrs. Steelpole opened the door and said, "I know you didn't bring any pajamas or anything, Tommy, but I laid out something comfortable for you on Jay's bed. Please put it on and come say good night to us when you and Jay are dressed." Normal. Still normal Jay was smiling sweetly when he closed the bedroom door. Tommy looked around. He thought he was in the wrong bedroom. Was this Jay's sister's room? No. Jay was an only child. It didn't feel like a boy's room. Things were pink. And frilly. And where did that big, queen-sized bed come from? Kids had single beds. Or bunk beds. Also, why were there three-full-length mirrors on the walls? Why was there a "vanity table" and stool, with another mirror? A lot of whys. Not normal. Jay smiled and said, "There's the nightshirt Mom picked out for you, Tommy. I hope you like it." Tommy looked at the garment. It was a nightshirt, just as Jay said. The kind that boys wore in the 19th-Century. Or in the Peter Pan cartoon movie. Except it was sort of an off-pink. 90% white. 10% pink. Pinkish. And it was sort of see-through. Not completely. It suggested, rather than revealed. Short, but not micro. Sexually ambiguous. For a sissyboy seeking to seduce an apprentice, it was the perfect starter set. Tommy didn't hate it. But he didn't like it either. Perfect. Tommy started to protest, but realized that, all-in-all, things weren't going nearly as gaily as they could have. So the pretty boy stripped down in order to put it on. Not looking at Jay, who was also getting nude. Tommy didn't look at Jay as he undressed. Had he looked, he would have seen Jay ogling Tommy's lovely nude body most unheterosexually. Tommy was a puerile delight, Jay thought during the three or four second interval between briefs removal and nightshirt putting-on. Jay caught a hot glimpse of Tommy's pert, brown nipples, his stunning ass and even his pink peener, which looked to be about half stiff in Jay's estimation. Another good sign, Jay believed. Tommy noticed that he was at half-staff as he put that odd nightshirt on and wondered why. Being naked in a room with a boy everyone said was gay was NOT a good reason for arousal, Tommy opined. It was a bad reason. But there he was. Avoiding eye-to-eye or eye-to-body contact with Jay was clearly the best course for Tommy. So the young beauty chose to look at himself in one of the room's mirrors. Oh! That was a mistake. Tommy didn't look like Tommy. He looked more like a girl, or a sissyboy, wearing a femmy nightie and looking quite sexy in it. Tommy had never been with a live girl wearing a sexy nightie, so his poor penis did what all penile members do in an unfamiliar-but-arousing situation do. It got aroused. And stood 100% tall. With its foreskin all the way back. Boy's goo oozing from its pouting peelips. Just from looking at himself in a "sissy side of androgyny" nightshirt. Tommy was horrified. Jay was delighted. Tommy stared at himself in his "tented" nightshirt and horrified himself for several minutes as Jay got undressed and into his night clothes. The veteran sissyboy stood behind his young apprentice-to-be and admired Tommy's reflection as ardently as Tommy did. Tommy only half-understood what was going on. He knew that he looked unlike how he usually looked. He looked "pretty." If that was the right word. Did he like looking pretty? He wasn't sure. But it was obvious that his penis enjoyed it. Tommy seemed to be mesmerized by his own image. His on-the-girl-side-of-androgyny image. So much so that he had forgotten that Jay was in the bedroom too. Jay! What must Jay be thinking of him? Did Jay think Tommy was gay? Was Tommy's hetero reputation, thus his life, over? OMG!! Jay was standing right behind Tommy. Was Jay admiring himself, or was he admiring Tommy? Jay appeared to be admiring Tommy. Strangely, Tommy liked that. He liked being physically admired. Even by Jay. No one had ever physically admired Tommy before. By physically admired, Tommy meant, the admirer's cock stiffened. And Tommy was pretty sure that Jay's cock was stiffened from looking at Tommy. Oh no! Tommy felt the tip of Jay's cock just glance Tommy's back!! Gay alert! Tommy should move. Put his clothes back on and run home. But he didn't. Instead, he moved away from the mirror, took three steps away from Jay and turned around. To look at a smiling Jay. Whose night clothes differed from Tommy's in many significant ways. First, while Tommy's outfit was ambiguously androgynous, Jay's screamed "SISSYBOY!!" Second, while Tommy's outfit was vaguely pink, Jay's screamed "PINK!!" Third, while Tommy's outfit was vaguely translucent, Jay's screamed "TRANSPARENT!!" And, while Tommy's outfit was short, but not micro, Jay's screamed, "LOOK AT MY COMPLETELY EXPOSED, COMPLETELY ERECT PENIS AND ACCOMPANYING TESTICLE BAG!!" Tommy was horrified. Sort of. Not completely disgusted. A little disgusted. As evidenced by his penis's frantic twitching when Jay revealed himself to Tommy. Let's analyze Tommy's thought process at that moment. Realizing that much of the blood that normally fed his brain was feeding his penis. Tommy had had no erotic experience with girls. Tommy had hormones. Active ones. Tommy had little hope of having any significant "experience" with girls for three or four years. Maybe longer. Jay looked more girly to Tommy at that moment than Tommy had ever seen a girl look. And Jay was, Tommy had to admit, exquisitely pretty. By Monday, everyone in school would know that Tommy had slept over at Jay's house. So everyone would think Tommy was gay anyway. Janis Joplin said it. "Freedom's just another word for nothin' left to lose." Tommy wasn't "all in" with Jay yet, but he had his hand on his chips ready to push them forward. Jay sensed all that and made three first moves. One: "You're very pretty, Tommy!" Two: Jay stepped forward and touched, with one finger, through Tommy's nightshirt Tommy's dripping peelips. Three: Jay leaned forward and gave Tommy a closed-mouth, three-second, kiss on the lips. Oh! Oh! Tommy was within a smidgeon of shooting his sperm. But Jay stopped. "Let's go say goodnight to Mom and Daddy. Then we can get into bed together." Tommy's unrelieved balls ached. Did he want to get into bed with Jay? YES! Even though it was gay? YES!! Did he want to wait until he went downstairs and said goodnight to Jay's parents? NO!!! But that was the agenda. That time, when Tommy offered Tommy his hand, Tommy took it. Which struck Tommy as odd, but appropriate. Tommy just wanted Jay and his parents to get the good night ritual over so that he and Jay could start to do that "bed together" stuff quickly. Halfway down the stairs, Tommy remembered that he was going to be greeting the Steelpoles while holding their sissy son's hand and sporting the biggest, neediest erection Tommy had ever had. But it was too late to back out. The Steelpoles were playing a card game when Tommy and Jay appeared and neither seemed to be put off in anyway by seeing two 11-year-old boys with fat erections and wearing girlish nighties. Jay's nightie being ultra-girly. Jay beamed with good humor as he kissed his mother on the cheek, wished her a good night, then sat on his Daddy's lap! Tommy, who was about to kiss Jay's Mom on the cheek, then shake Jay's Daddy's hand or something, was astonished. Jay's bottom was bare. His nightie had ridden up and his stiffie and balls were fully exposed. And he was kissing his Daddy open-mouthed!! With tongues!! Tommy was momentarily distracted by Jay's Mom, who said, "You look very pretty in that nightshirt, Tommy. Jay picked it out for you. Next time, I think you would look great in one of Jay's babydolls." Huh? What was she saying? All Tommy could hear were Jay's moans as his Daddy pulled Jay's foreskin up and down as they kissed good night!! Tommy's ears were boiling hot. And he felt some pangs of impending something in his loins. Jay's Mom was saying something else: "... nice that Jay and his Daddy have such a loving relationship, don't you?" Huh? Tommy looked at Jay's Mom with erotic terror in his eyes. Then at Jay and Daddy. Jay was grunting and squealing and gasping for breath until... Jay was shooting strands of thick boy's cream into the air. Some landed on the floor. Some on Jay's nightie. Some on Daddy's clothes. And some onto Daddy's skilled hand. Daddy licked his hand clean. Then gave Jay a second tongue kiss good night. Jay got off of his Daddy's lap and offered Tommy the lap seat. Tommy hesitated. Was he going to be so tarty and stupid that he, a virgin and avowed heterosexual would sit on the lap of a man he had only met hours earlier? A man who had just tossed off his own son while the boy's mother and house guest watched? Apparently so. Tommy climbed onto Jay's Daddy's lap and awaited his gay fate. It was easy to rationalize. It was apparent to Tommy that he needed to orgasm as soon as possible. Delay of even the time it would take Tommy and Jay to get upstairs and into bed could mean serious injury to Tommy. Mr. Steelpole, a responsible adult and caring parent, recognized that potentially critical condition and applied "first aid" to his son. The man must surely recognize the same condition in Tommy. So Tommy was only receiving first aid. From a very hunky, handsome man. Not only that, but there was basic fairness involved. Two pre-teen boys at one boy's house. The host boy, Jay, had gotten something. So it was only fair that Tommy, the guest, get something too. Tommy settled his bare bum on Daddy's lap and felt the man's lead pipe rubbing Tommy's left hip. Oh! Should Tommy touch it? That would be the mannerly thing for a guest to do, wouldn't it? Maybe later, though, because Daddy was sucking Tommy's tongue! Then getting his hand acquainted with Tommy's stiff, aching cock. Tommy was overwhelmed with unfamiliar and highly erotic feelings. A big, handsome, powerful man was kissing Tommy and tossing the young beauty off as Tommy grunted and groaned and completely surrendered. None of which Tommy would have considered plausible mere hours earlier. Had Tommy abandoned all of his "morality" and heterosexuality in order to get a few, quick, cheap thrills? Apparently so. And quite eagerly, judging from the way the boy was rubbing his hip against Mr. Steelpole's cock as they kissed. The man was molesting him so beautifully. He had never felt anything one-hundredth as good. And then, the crisis got critical. Tommy felt that stirring he had felt with Jay, only far more powerfully. His little nuts were aching for fulfilment. A feeling that the totally virgin-to-orgasms boy had never felt. It was awesomely terrifying. Disgustingly beautiful. Shameful. Wrong. Gay. Oh. Oh. Tommy was shooting his sperm into the air for the very first time! The boy was in erotic agony. His nuts felt as if someone had slid fireworks into his wrinkled, pink bag, then set them off. It was the single best experience of his life. And the worst. Because Mr. Shame and Mr. Guilt had made their unwanted entrance. Tommy probably would have invited them to sit down. Have a long discussion. Listen as they suggested that he grab his clothes and run home. But once again, Mrs. Steelpole stepped in with some pseudo-normality. "That was so nice, Tommy," she said. "I'm glad you enjoyed it so much. My Harold is so good at making a pretty young boy happy before he goes to bed, isn't he? Don't worry about reciprocating for Harold just yet. I'm sure you boys have a lot to do upstairs. I'll just help Harold out. Oh, look how much you've excited him. He thinks you and Jay are the prettiest boys in town." Tommy blinked. Looked around to make sure he was still on planet earth, then looked at Mr. Steelpole. The man's huge cock was exposed, standing tall and dripping furiously. It was a frightful and appallingly erotic sight. So was Mrs. Steelpole kissing her husband as she manipulated his penis. Tommy felt Jay's hand leading him away and upstairs. "Let's give them some privacy," Tommy's sensei said. Mr. Shame and Mr. Guilt appeared to have been given the bum's rush. Because as Tommy and Jay entered the bedroom, Tommy was ready to learn new tricks. Jay was almost ready. "I don't want us to have our first real fun together with you looking so frumpy," Jay said. "Mom is a sweetheart, but she's so conservative about boys other than me wearing pretty things. Let me find you something prettier. You can take that old nightshirt off while I look." Jay wanted Tommy to get completely nude?!?! Then put on something as girlie as Jay was wearing? Sounded good to Tommy. Tommy slid his nightshirt over his head and stood nude, facing Jay's back. Oh my. Jay was bent at the waist. Looking for a nightie for Tommy in his bottom drawer. And showing Tommy his entire, bare bum. Even the pink, wrinkled part! Tommy's penis sprang to full attention!! And the boy, driven by forces he only half understood, closed the gap between him and Jay. He reached forward with his right hand and softly touched Jay's anus with one finger. Jay, long accustomed to male fingers touching his anus, didn't flinch. But he was once again delighted at Tommy's progress. And Tommy's reverential touching of what Mr. Chaucer, Jay's English teacher called, "the best asshole on the planet." Jay reached forward and grabbed the garment he had located much earlier, but wanted to give his apprentice a "bum show." Then the lovely sissyboy stood, turned around and said in a breathy voice, "That is so nice, honey. Let's save all that for when we get you dressed and get into bed. Though I must say, you look awfully good naked." Tommy was rampant and impatient. But he liked the compliment. And he liked the tiny, white babydoll Jay handed him to put on. It had two thin spaghetti straps at the shoulders, a filmy body and ruffled skirts that exposed all of Tommy's "best parts" to Jay. Jay allowed five minutes of Tommy's self-adoration in a mirror. He considered it foreplay. But then he was ready and randy and could wait no longer. "Come to bed, Baby," Jay said. "Let's make each other happy." Tommy would have been OK with five more narcissistic minutes, but the "happy" stuff sounded great. Jay pulled back the clean top sheet. Tommy and his new best friend forever, Jay, got into bed together. Tommy lay on his left side. Jay on his right. What a sexual feast each boy contemplated. Jay couldn't decide what he wanted to do first. Tommy's creamy shoulders above the white, virginal nightie bust, invited kisses. As did Tommy's neck and lips. Tommy's white spaghetti strap could be easily turned down, exposing a puffy nipple for Jay's adoration. Jay hadn't inspected Tommy's pretty toes yet, but that was on the agenda. As were all the usual hot spots – prick, balls, bum. Yum! It was a lovely tableau. Pink-clad Jay on the right. White-clad Tommy on the left. Two lingerie sissies. One veteran. One rookie. Kissing. Hugging. Tommy mimicking Jay. Jay cupped Tommy's lovely right bum cheek in his left hand. So Tommy cuddled Jay's left bum cheek. Jay slid a finger between Tommy's bum cheeks and slid a finger into Tommy's anus. Oh! Tommy didn't copycat right away. He was reveling in the crazily unfamiliar and deliciously erotic feeling of a finger in his bottomhole! Right in his bottomhole. Not prostate-deep. Not yet. But still wildly exciting. Rather than reciprocate, Tommy followed a bigger urging. He tried to rub his dripping cock knob against Jay's stiffie. Showing great erotic creativity, Jay continued to tongue-kiss Tommy's mouth and finger Tommy's bumhole. And he added a third element. With his free hand, Jay grabbed his own cock and Tommy's. He positioned the "arrowpoints" of both cocks rubbing each other. As their boyish penises continued to drip profusely. Jay held onto both knobs. Rubbing their most sensitive parts against each other. As they kissed. And Tommy's virginal bum happily endured its first "guest." It was an erotic masterpiece. That deserved a very large, very intense and cum-drenched climax. Oh yeah. It was messy. And ferocious. With lots of sissyish squealing and squirting. Tommy asked himself, where had all that been all his life? Making love and cumming were his new and permanent passions. Sissy juice was everywhere. And Jay knew just what to do with it. The delicious pink sissy began to lick it all from Tommy's private areas. Tommy liked that. Especially when Jay started licking the cum from Tommy's balls. And then, [gasp], his shriveled penis. Which made it start to unshrivel. Oh dear. Jay had Tommy's little cock in his mouth! And was licking the knob most deliciously. Poor Tommy. He hardly knew how to act, his senses were overloaded. So he just squealed and squirmed and squirted yet again. Mmmmmm. That was a seismic stunner! Right into Jay's pretty mouth. Jay knew what to do with a mouthful of Tommy's sperm and semen. He kissed Tommy with it. Feeding him his own sissy cream. Tommy devoured it. When it was all gone, Tommy proposed that he satisfy Tommy the same way that Jay had satisfied Tommy. Jay eagerly agreed. The pink beauty lay on his back, skinned peener standing tall as Tommy knelt to Jay's left side. Tommy kissed Jay's balls first, drawing appreciative grunts from his lover. Then he licked Jay's cockshaft thoroughly. Cleaning it of all the cum he and Jay had spunked up earlier. With all but Jay's cock-tip tidied and tongue-washed, Tommy began to adore Jay's knob. It was so good that tears came to Jay's pretty eyes. And Jay was a young man with wide sexual experience. Jay held his nightie skirts up so that Tommy could have full access. He saw Tommy's head bobbing on his cock and was amused that his prediction of 12 hours until Tommy would be sucking Jay's cock and swallowing his cum was a gross overestimate. It took less than four hours. Because Jay was spunking hard and Tommy was swallowing as fast as he could. Tommy LOVED sucking Jay's cock and he LOVED swallowing Jay's cum! He LOVED all the naughty things that Jay, and don't forget Jay's Daddy, did to make Tommy cum. Was Tommy gay now? Probably. Did that sadden or frighten Tommy? Not one bit. His only question was, what next? There were many possible answers to that. And Jay would get around to doing "nexts." Just as soon as he dealt with an all-powerful "nows." Novice Tommy had sucked Jay's cock like a $1,000 Vegas hooker. And Jay's recovery was a slow one. Overeager Tommy kept licking and sucking Jay's penis until Jay had to ask him to stop. So they tonguekissed. And played with each other's nipples and penises. Until they were both rock-hard again. What a glorious evening that was. And it wasn't over. "I'm going to eat your pussy, Sweetie," Jay announced. Tommy shuddered with fear and lust. "Will it hurt?" he murmured, in the sissiest voice. "Only if I bite. And I promise I won't. Now just lie on your stomach and open your legs a little. That's it. Mmmmm." Tommy didn't realize until that moment that a) he had a "pussy" or b) that it was edible. But he sure found out. Jay's tongue dug into Tommy's asshole. Which made Tommy whoop with surprise. Then settle down so that Jay didn't get seasick from Tommy's squirms and have to stop feasting, Tommy didn't want Jay to stop. But Tommy couldn't control all of his squirms. It was that fabulous. Who could have believed that someone would do that for someone else? Or that it would feel so fantastic? Jay didn't seem to mind the taste, the smell or the depravity of it all. The pink sissy just wanted to make the white sissy happy. He was doing a really good job at that. Tommy was gasping and groaning and squealing most unmanfully. Jay would tongue-dig mercilessly, then withdraw and lick Tommy's pink danglers. Then return to his excavation duties. Tommy would make the squeakiest noises. And then Tommy would cum! Gloriously. Twice. The boy was flushed-faced and ball-drained when he felt something else going into his boyish bum. Jay's fingers were inside Tommy's moistened hole. And Tommy's fevered brain was just rational enough to realize that Jay's fingers were extra-slippery. It was Spermbutt Anal Lubricant, of course. The choice of responsible buttfuckers worldwide. Using three fingers to dilate was an additional sign of Jay's responsibility. Tommy didn't know that. And he didn't know that Jay's moves were well known in the "anal enthusiast" community as a prelude to assfucking. When Tommy got up that morning, he could never have imagined that he would be in love with a sissyboy whose cock he had eagerly sucked, whose cum he had eagerly swallowed and who was about to inquire about fucking Tommy. Which is what happened. "I see you like anal play, Honey," Tommy looked back at Jay with teary eyes and said, "unnhh." "There's more to anal play, Tommy. I can do something now that will send you out of the solar system. Would you like me to do it?" Tommy gurgled, nodded and said something that sounded positive. Jay took that as permission to fuck Tommy. Jay positioned Tommy on his knees, ass up. Tommy trusting Jay. Perhaps too much. Tommy was so sex-beaten that he didn't really notice Jay lubing up his 4.56-inch stiffie with Spermbutt Anal Lubricant. Tommy thought that Jay would be spelunking into Tommy's love cave with fingers or tongue again. No. Jay slid his fine young cock right into Tommy's hot, wet and very surprised butthole. Tommy's pretty eyes opened wide! Was that Jay's cock in his bum? Was Jay's cock what Jay said would send Tommy out of the solar system? Was Jay FUCKING Tommy? Yes, yes and oh yes. Did Tommy want to be fucked? Apparently so, since it was probably the most awesome feeling Tommy had ever had. Tommy was being fucked. By the Love of his Life. With whom he had dreaded being seen earlier that day. Tommy was being fucked and had to wonder if he was now officially gay. Would he be entered on a "master list" somewhere, after some sort of public ceremony? Would there be some sort of "shaming ritual," where he would be cast out from heterosexual society? Tommy would just have to worry about that later. At the moment, Tommy's prostate was receiving its first-ever cock rub. It felt so unexpectedly amazing that Tommy was sobbing his pretty eyes out in helpless pleasure. His ass had never felt so alive. His mouth was babbling as his body surrendered completely to Jay's relentless passion-piston. Poor Tommy had no sperm left in his pretty bag. His cock wasn't even one-quarter stiff. But his guts were on fire. Tommy was trembling and his pretty eyes were filled with wet, fuck-me-harder tears. And then it happened. The Big One. The boy's first anal orgasm. So different than the mere penile variety. So complete. So feral. So animalistic. Tommy could become a surgeon some day, because he had witnessed how one's guts are torn out and then thrust back in. For Jay's part, he was experiencing the perspective of fucking that he usually missed. Jay loved being little Miss Sissy-on-the-bottom. But now and then, he also enjoyed being Mr. Take-my-big-dick-you-little-pussy-on-the-bottom. And the hot loads that the topper engenders for himself and his "victim." Jay's hot load was on its way. How could Jay hold back for long after the bottom-cum that he had just felt Tommy shudder through? Plus, Tommy's orgasmic contractions had gripped and grabbed Jay's cock in ways too erotic to describe. So Jay also expended the last of his ADCs (allotted daily creamies) and adored the agony his ecstasy forced on him. When Jay's limp cock was ass-muscled out of its happy home, the boys kissed and cuddled for a moment, then fell asleep. Exhausted, but happy. Three – Boy meets man Tommy was in school. Walking down the hallway between classes. That was normal. But what he was wearing wasn't. Tommy was wearing the white babydoll nightie with spaghetti straps that he wore for his night with Jay. But he had accented the sissyish attire with a pair of white, thigh-high stockings and [blush] a pair of white, three-inch-heeled slippers with a big, white powderpuff at the instep. No panties. So everyone could see Tommy's stiff prick and dangling dazzlers. Some of the school boys watching were catcalling and harassing him. Others had their cocks out and were masturbating as they saw Tommy. But Tommy didn't care. He was walking toward Mark Firmcock, a studly 8th-grader whom Tommy had seen now and then in school. Mark was two years older than Tommy and was very handsome. Mark wanted Tommy. Mark wanted to take all his clothes off and get into bed with Tommy, then kiss him all over. Mark wanted to put his big penis into Tommy's bumhole and make Tommy feel good. Really good. Mark held his arms out to Tommy. Tommy was in Mark's arms. Mark and Tommy were almost kissing. And Tommy woke up. Because Jay was thrashing around in bed and he kicked Tommy inadvertently. Tommy took a moment to wake up. Why was Jay thrashing? Tommy opened his eyes. It was morning. The morning after the most wonderful night of Tommy's life. Where was Jay? The sissyboy Tommy loved. Tommy looked to his right. Saw Jay. And someone else. Tommy rubbed his eyes. Opened them again. It was Mr. Steelpole!! Jay's Daddy! He had Jay on his back. Jay had his ankles up to his ears. Mr. Steelpole was on top. And he was FUCKING Jay!!! His own son!! Thrusting that cock Tommy had only seen briefly last night into Jay's too tiny bumhole. He was KILLING Jay! Wait. Maybe he wasn't killing him. Jay seemed to be enjoying his Daddy's cock inside of him. Enjoying it a lot. Tommy could see where Jay had already spunked onto his own tummy and looked ready to spunk again. But incest!?? Man-boy sex?!?!? Ick. Right? It didn't seem too icky to Jay. Or Mr. Steelpole. They both seemed to be enjoying themselves very much. Jay was squealing louder than he had when he and Tommy had made love. And Tommy remembered some show he had seen on Discovery Channel where a lady was giving birth. It seemed that Jay was putting the same kind of effort into giving birth to his next orgasm. And from the look of blissful torment on Daddy's face, Jay's Daddy felt the same. They were definitely enjoying themselves and about to enjoy themselves a lot more. Tommy didn't exactly jump out of bed when he witnessed this incestuous, illegal, homosexual tableau. But he did vacate the bed and move to the other side of the room. Where he could get a better perspective on the wonders of man-boy sex. Neither Jay nor his Daddy noticed. This lovely fuck had happened because Mr. Steelpole couldn't be content with a goodnight French kiss and mutual wank off from his son any more. The previous evening, the man had had to whack off not only his son, but Jay's pretty friend, Tommy. Then, instead of having Jay reciprocate with a nice, kissy, wank from Jay, Mr. Steelpole had to settle for his wife's half-hearted effort. Not only that, but it had been Friday. And Friday was the day that Jay was supposed to suck his Daddy off and swallow all his sperm. Jay's Mom had agreed to that, as long as the blowjob was confined to Fridays and the other six nights were merely mutual wanks. Like most women, Jay's Mom lived in mortal fear that her husband would enjoy himself too much. By an "agreement" that Mr. Steelpole didn't agree with, he wasn't allowed to fuck Jay. Imagine that. A Daddy unable to fuck his son! A boy as beautiful, randy and gay as Jay, who was giving it up to any man who smiled at him. So Daddy was stuck with his wife coaxing a few dribbles out of him, as Jay and Tommy went off to a night or orgasmic delights. Each scream of passion Daddy heard from Jay's room that night just pissed him off that much more. So at first light, Daddy damned the torpedoes, left his sleeping wife and stormed into Jay's room. The sight of two cum-stained, sleeping, lovely boys in girlish nighties had fire spewing from Daddy's nostrils. Worse, Jay was lying on his stomach. Bare bum pointing at his Daddy. ASKING for it! Though he was quite asleep. No matter, in Daddy's fevered mind. Daddy snapped. He bent over the side of the bed, parted Jay's bum cheeks with his fingers, and began to lick out Jay's bum hole. That was, as we say, a "waker-upper." First Jay thought he was being eaten out by Tommy, and that Tommy would be fucking Jay. Which would have been fine, since Jay had "done the honors" with Tommy the night before. He purred nicely at the thought. But as he awoke, he saw Tommy next to him, his lovely chest rising and falling in slumber. Huh? Could it be? It was!! Daddy was about to fuck Jay at last! Jay looked over his shoulder at Daddy. It wasn't polite to interrupt him while he was eating, but Jay said, "That's awesome, Daddy. Please fuck me." Daddy intended to. And two minutes later, having lubricated Jay sufficiently by his standards, Daddy flipped Jay onto his back, then mounted his son and entered his bum with his cock." Landed at last. One small step... Houston, no problem. So good. So tight. So wet. Better than pussy. And Jay was so responsive. Two minutes after entry, as Daddy was kissing Jay and fucking him hard, Jay shot his spunk all over himself. Moments later, Daddy and Jay could feel Tommy awaken and move out of bed. They would deal with that later. There were orgasms to shudder through. Big ones. Daddy's ballbuster collided with Jay's after 18 minutes of furious physical activity. Not the least of which involved Tommy on the other side of the room, trembling with fear that the crazed sex-wolverine that had once been Mr. Steelpole would want to FUCK Tommy next! Or that he wouldn't want to! Father and son cuddled and kissed after their mutual nutblasts. Falling in love with each other in a different way. Jay began to fondle Daddy's penis as they kissed. Doing what just-fucked boys who want to be twice-fucked boys do. Daddy was responding. Tommy was wondering if he should go fix himself a bowl of Cheerios and see what Scooby-Do was up to at the Old Facepaster Mansion. If Jay gave Tommy the slightest whiff of encouragement, Tommy knew that he would join the incestuous couple in their pit of sin. Tommy would be kissing and sucking on that horrible monster of a poop-and-cum-stained cock. Terrorized at the prospect of Mr. Steelpole shoving it into Tommy's virginal-to-men bumhole. Making Tommy cry out in anguish as the cruel beast pushed and humped into Tommy's tiny orifice. Ripping and ravishing Tommy's most intimate areas! Tommy wanted that! All of that! But no. Jay was being piggy. Keeping his Daddy and his Daddy's big prick all to himself. Mr. Steelpole was being piggy too. Ignoring the basic rule of hospitality: One doesn't take sustenance while one's guest is hungry. Hmmmmppph! It might just be some time before Tommy came back to the Steelpole house for his fuckings. He would have no trouble finding others willing to make love, real love, to him. Tommy was sure of that. So the newly-minted sissyboy stormed out of the room, walked to the kitchen and realized that he was in no position to go home or anywhere else. First, it was too early in the day to go home. Tommy was pretty sure that his Mom was entertaining a man in her bed. It wouldn't do to walk in on her. Then there was the matter of how he was dressed. White babydoll. With dried cum all over the nightie. And Tommy's body. Tommy had no idea where his boy clothes were. The nightie was so short that all his "things" were exposed. And he had no panties, let alone trousers. [Sigh] Maybe Cheerios and Scooby-Do it would be. Rats. He didn't even know where the cereal was. Or the TV remote. Just then, Jay's Mom, Mrs. Steelpole, appeared. Which scared Tommy for two reasons. First, he was a walking CSI project of bodily fluids, crossdressed for frantic, homosexual sex. Would Mrs. Steelpole call him a disgusting little faggot who corrupted her pure, mostly hetero son? Second, and this was the really scary part, was the way she looked. No makeup. Messy hair. Flannel shirt and jeans that made her look more like a lumberjack on casual Friday than a 30-something married woman with a husband to please. (Where did Tommy get such ideas? Were "Leave it to Beaver" reruns on Netflix again?) Fortunately, when Jay's Mom spoke, she was the same accommodating hostess that she had been the night before. "Tommy, darling, I see that you and Jay had a fun night. He's such a doll, isn't he? And I'm sorry about Jay getting stolen from you by his Daddy. But I always knew my Harold wouldn't be happy until he got that big cock of his right up Jay's bum. "Oh well. I'm sorry you got cheated out of your morning orgasms with Jay. How about some eggs?" To that odd soliloquy, Tommy could only say, "Please." Little was said as Tommy and Jay's Mom ate their eggs, toast and sausage. Mostly because Jay's Mom was being so empathetic that Tommy was afraid she might offer to skin Tommy's peener for him or something. Tommy did NOT want that! What he did want was to shower and go home. After he helped Jay's Mom clean up, it appeared that Tommy would get his wish. But just as Jay's Mom was getting him clean towels, Jay and Mr. Steelpole appeared. Jay was wearing an odd expression. And nothing else. The expression said, "I'm sorry we crowded you out of bed this morning, but the Daddy-fuckings were awesome!" The nudity said, "The Daddy-fuckings were awesome!" Mr. Steelpole was wearing a robe. And as Jay escorted Tommy from the kitchen, the boys could hear Mr. Steelpole telling his wife that they would be going out later that day and buying that new living room set she liked as soon as he showered. Then correcting himself by adding on that new dining room set. Which in the Steelpole household was apparently the price for three monumental bouts of incestuous anal sex. Jay led Tommy back to bed. And Tommy pretty much forgave Jay during the orgasm he had while sticking his needy cock into Jay's Daddy-buttered bum. Mr. Steelpole delivered Tommy to his house at precisely 9 a.m. Leaving Tommy to reflect on what he had learned in the past 18 hours. And how to build on those learnings. Jay had vowed to Tommy that the new sissyboy was Jay's apprentice and that he would not abandon Tommy's development, even though Jay and his Daddy would probably be fucking at least twice a day for the foreseeable future. OK. More like three times a day. Or four. Jay had also given Tommy a "goodie bag" of things an apprentice might need to get started: three pairs of sexy, skimpy panties in black, yellow and pink; two tiny nighties in pink and black (!); two pairs of stay-up stockings (like those in his dream) in black and tan; a big bottle of Spermbutt Anal Lubricant; another bottle of Slickyboy Masturbation Cream (a Spermbutt Industries product); and seven back issues of "Sissy Boy" magazine to stir Tommy's imagination. But Tommy still felt betrayed. Just when he was falling in love with Jay, Jay was distracted by his Daddy's carnal attentions. Jay preferred a hunky, handsome, big-dicked, randy man over his sissyboy boyfriend! Tommy had had no experience with men, but he could see where Jay's choice may have made sense. [Sigh} Tommy let himself into his house, scooted up to his room, concealed his stash of sissy stuff and went off to find his Mom. Who wasn't home. But appeared at the door at 9:11. Flushed in the face. Walking stiffly. But seemingly very happy. It appeared to Tommy that he and his Mom had had similar evenings. Mom greeted Tommy affectionately, but with little curiosity. Lest Tommy start asking questions about her night at Bradley's place. Wordlessly, mother and son went off to take well-needed naps. Tommy awoke at 1:07 that Saturday afternoon when Mom handed him the phone. "It's your friend, Jay," Mom said. "Lunch is ready when you're done talking." Mom left Tommy's bedroom and Tommy said, "Hello." "Tommy, I didn't abandon you. I got you a sleepover date tonight with Carter Buttsplitter. His Daddy will call your Mom as soon as we hang up." Tommy's cock stirred at the prospect of a second night of penile passion. But wait. Tommy remembered Carter from elementary school. Wasn't Carter older? Fourteen and a freshman in high school, Tommy thought. "Is Carter a sissyboy?" Tommy asked Jay. "No. Definitely not. Which means you should wear the black panties under your boy clothes, and take the black nightie and the Spermbutt Anal Lubricant. You're gonna get fucked tonight. All night long." Tommy shuddered with fear and lust. Jay was forgiven. Mostly. Four – Boy meets older boy Tommy sat in the back seat of Mr. Buttsplitter's car as the man drove him and Carter to their house. Despite Jay's assurances that all would be way better than well, Tommy was VERY nervous. Jay had told Tommy that Carter had a man-sized cock (Jay knew first hand) and that at some point, he may receive some attention from Mr. Buttsplitter, who was every bit as hunky as Jay's Daddy. Was Tommy ready for a man-sized cock in his tiny bum? The boy couldn't imagine a future without man-sized cocks in his tiny bum. Mom had been more than willing to hustle Tommy off to a second sleepover with a three-years-older boy whom Tommy barely knew. Bradley was waiting for her after all. In the back seat with his "sleepover date," Tommy was sneaking little peeks at Carter as Mr. Buttsplitter drove. Carter was dishy! And he seemed smitten with Tommy already. Which was why Tommy willingly took Carter's offered hand. Then allowed Carter to kiss him – lips only. Which escalated to open-mouths and tongues. And, since it's not really kissing until the cocks come out... The cocks were out. Mmmmm. Carter knew how to manipulate a foreskin as he tongue-kissed a sissyboy! Tommy knew how to issue squeaks and grunts of pleasure as he rubbed his soft hand up and down Carter's almost-manly cock. And Mr. Buttsplitter knew how to bide his time, letting his son Carter have the first two or three fucks, then step in for his own fun when Carter needed a break. The three arrived at the Buttsplitter residence a few seconds before the boys would have spunked. Which was economical, since sweet spunk should be swallowed, licked up, or driven deep within a pretty boy's bowels, not flung into the air. Mr. Buttsplitter led the boys into the house, noting that they had not bothered to put their cocks away. Quite a connection they had established already! Tommy held onto his goodie bag of lingerie and lube, realizing that Carter was already so sexed up that no pause to sissy up would be necessary. At least for the moment. So Mr. Buttsplitter said, "Go have fun, boys. I'll see you later." And he winked at Carter. Carter knew that the slight cost of his wide-open freedom-to-fuck-gorgeous-young-boys-in-his-own-house was that his Daddy got a fuck or two, if the boy was willing, of course, from each of Carter's dates. Carter and Tommy sped upstairs to Carter's room, which thankfully sported a queen-sized bed and three full-length mirrors. Tommy only had time to glance at that as he tossed his bag aside and stripped to his skimpy black panties. Carter was nude, lying on his back in bed, as Tommy gave Carter a little, teasy, take-off-the-panties-inch-by-inch show. Carter gasped appropriately when Tommy exposed his stiff peener and little peanut bag. But the biggest gasp was reserved for the exposition of Tommy's ass! It was the finest boy bum Carter had ever seen. And Carter had seen, and fucked, a lot of them. Beginning with Jimmy Pinkbum. Carter met Jimmy three days after Carter's 10th birthday party. Carter remembered it all so well because after all the kids left the birthday celebration, Carter's Daddy tried a "homo top" on him. Carter let his Daddy know that any such "homo top" moves would be executed by Carter. Carter was NOT a sissyboy. He was to be, in the shortest order possible, a sissyboy lover. Mr. Buttsplitter was wise. He backed off from trying to fuck his son and focused on fucking the boys whom Carter was fucking. Or had fucked. Especially the "had fuckeds." The exes. Three days later, Carter seduced eight-year-old Jimmy. Warmed Jimmy up with some kisses, nipple sucks and fingers in Jimmy's bum. Lubed Jimmy with some Spermbutt Anal Lubricant. And fucked him. Bold as you please. With Mr. Buttsplitter sitting in the family room downstairs, listening to all those screams and squeals. Carter and Jimmy had a hot little love affair for nearly three weeks. When they broke up, Mr. Buttsplitter and Jimmy had three fuck-filled weeks together. And so it went. And there was Carter, four years later. Looking at the lovely Tommy. Strip-teasing for Carter. Hungry for Carter's cock. It was good to be Carter. Tommy let his panties flutter to the floor. Then, most teasingly, he slowly walked over to the bed and lay next to Carter. Carter placed a hand on one of Tommy's hips, leaned over, and kissed the boy. Tommy was exceptionally aroused. It was so different being with Carter than it was with Jay. Jay had been "in charge" of the sexual proceedings, but, as a fellow sissyboy, Jay could never DOMINATE Tommy. Carter could DOMINATE Tommy. Tommy could be the helpless little sissyboy, subject to every one of Carter's disgusting, erotic urges. Oh! It already felt so good to be dominated. Carter was licking out the inside of Tommy's mouth. Tommy's tongue was transmitting a message through Carter's tongue, "That's right. Tonight, I'm your possession. USE me! Satisfy all of your filthy needs with me. I'm your sissyboy!" Carter, who was used to getting such tongue transmissions, answered back by entering Tommy's bumhole with one dry finger. Tommy gasped. And rubbed his needy prick against Carter's hairy thigh as they kissed more urgently. Carter knew just where Tommy's pleasure button was, but he wasn't going there just yet. Carter withdrew his finger and stopped the deep kiss, engendering a whimper from Tommy. "Lick my fingers, Baby," Carter said. "I'm going to run around in your playground before we fuck." Tommy wasn't clear on the metaphor, but eagerly licked Carter's three fingers, including the one that had been in Tommy's pooper. The metaphor crystalized in Tommy's mind when Carter's three fingers stretched Tommy's "pussy" and found the capital city of the Land of Boyish Pleasure. Tommy's pretty eyes widened and filled with tears as Carter mercilessly assaulted Tommy's prostate with his insolent fingers. Tommy GAVE himself to Carter! Anything Carter wanted from Tommy was his! Carter got that a lot. And he never tired of it. Carter was a benevolent despot. He believed that his lovers should enjoy their sexcapades together as much as Carter did. So he was going to give Tommy a nice screaming-for-his-momma, near-death-experience orgasm before things moved on to Carter's pleasure. Carter delivered just that to Tommy. Tommy briefly wondered how he had been able to exist as the dull, non-sissy boy he had been 26 hours earlier. The old Tommy had been shackled to the earth. The new Tommy soared through the universe on the warp-factor-25 starship, H.M.S. Anal Orgasm. . Tommy was a weeping, blabbering mess of spunking sissyboy Just what he and Carter needed him to be. And Carter did Tommy the sweet courtesy of licking up Tommy's thick, creamy, first-of-the-session spermstorm. Was Tommy in love with Carter too? Maybe. Love seems to follow nuclear orgasms, doesn't it? Tommy spread his legs. Lifted his knees and begged Carter to fuck him. A true expression of the Love thing. Carter mounted his new BFF, lined up his penis with Tommy's asshole and pushed. Oh!!! It stung Tommy a little, Carter being bigger than Jay had been. But the pleasure was immense. Punctuated by some outstanding lovemaking skills from Carter, who knew what a sissyboy wanted from a fuck. Carter whispered soft words of love in Tommy's ear as his cock distressed the boy's semi-sore prostate. When not saying endearing things, Carter was licking and sucking Tommy's tongue. Oh! Or his nipples!! Oh!! Oh!! The whole "gay" thing was really working out for Tommy. Being the less-experienced lover, as well as the one whose prostate was being tortured, Tommy spunked first. Which set Carter off. A cum that startled the semi-jaded Carter in its intensity. Carter hadn't fallen in love since he was 12. He fell again. Daddy wasn't getting any that night. Tommy was all Carter's. Tommy's apprenticeship was off to a great start. NOTE: When I first wrote this, I was thinking a three-parter: "Sissyboy Apprentice," Sissyboy Journeyman," and "Sissyboy Master." But the plots aren't forming in my head yet. What do you think? Also, looking back at some of my older stuff, it seems that some other stories need a chapter two, notably: "Sissyboy Nephews" and "Sissyboy Island." "Sissyboy Prom Night" seems to need a part three, as does "Sissyboy Adultery." I liked "Sissyboy Island" when I wrote it, but not one reader said anything about it. And, being whorish for reader comments, I moved on. But the residents of that island deserve better. Again, what do you think? My older stories on nifty: "Sweetyboys" (gay young friends) August 31, 2007 "Boarding-School Bedmates" (bisexual adult-youth, though it's quite gay) May 5,2008 "After-School Stroke Club" (gay high school) May 28, 2008 "Pretty" (gay adult-youth) May 21, 2008 "Hotel Management" (gay adult-youth) June 2, 2008 "Dating Pretty Boys" (gay young friends) July 2, 2008 "Sissyboy Stepson" (gay adult-youth) July 30, 2008 "Sissyboy Showoff" (gay adult-youth) August 14, 2008 "Sissyboy Sleepover" (gay incest) August 26, 2008 "Cockteaser's Comeuppance" (gay adult-youth) September 5, 2008 "Schoolboy Pleasures" (gay adult-youth) October 23, 2008 "Home-Schooled Sissyboys" (gay incest) October 25, 2008 "Sissyboy-Daddy Reunion" (gay incest) November 24, 2008 "Sissyboy Shooting Lessons (gay adult youth) December 4, 2008 "Stepson Seduction" (gay incest) December 13, 2008 "The New Sissyboy" (gay incest) December 22, 2008 "Sissyboy Hangout" (gay incest) February 13, 2009 "The Little Prickpleaser" (gay incest) February 20, 2009 "Twelve" (gay incest) March 10, 2009 "Sissyboy Facts of Life" (gay incest) March 11. 2009 "Lord Upcock's Darlings" (gay adult-youth) March 12, 2009 "Sissyboy Spunk Party" (gay adult-youth) March 20, 2009 "Corporate Cockpleasers" (gay adult-youth) April 1, 2009 "Sissyboy Nephews" (gay incest) May 5, 2009 "Sissyboy Pediatrics" (gay adult-youth) May 14, 2009 "Next-Door Sissyboy" (gay incest) May 19, 2009 "Sissyboy Sanctuary" (gay adult-youth) May 20, 2009 "Model Sissyboy" (gay adult-youth) November 5, 2009 "Sissyboy Restitution" (gay adult-youth) January 27, 2010 "Sissyboy Spinoffs" (gay adult-youth) January 28, 2010 "Sissyboy Wives" (gay adult-youth) February 3, 2010 "Secret Sissyboys" (gay adult-youth) April 8, 2010 "Sissyboy School Spirit" (gay adult-youth) May 5,2010 "Try Men" (gay adult-youth) June 21, 2010 "Teaching Sissyboys" (gay adult-youth) July 26, 2010 "Sissyboy Princesses" (gay adult-youth) September 11, 2010 "Sissyboy Swap" (gay adult-youth) December 26, 2010 "Sissyboy Psychology" (gay adult-youth) January 12, 2011 "Sissyboy Island" (gay adult-youth) January 28, 2011 "Sissyboy Prom Night" (gay incest) February 8, 2011 "Sissyboy Workout" (gay adult-youth) February 12, 2011 "Naughty Sissyboys" (gay adult-youth) February 19, 2011 "Society Sissyboys" (gay adult-youth) February 28, 2011 "Sissyboy Sodomy" (gay adult-youth) March 22, 2011 "Sissyboy Stripoff" (gay adult-youth) April 5, 2011 "The Sissyboy and the Ruffboy" (gay adult-youth) April 5, 2011 "Sissyboy Superiority" (gay adult-youth) May 26, 2011 "Sissyboy Sex Education" (gay adult-youth) August 6, 2011 "Sissyboy Justice"(gay adult-youth) August 16, 2011 "Sissyboy Summer"(gay adult-youth) August 23, 2011 "Sissyboy Dreamer" (gay adult-youth) September 8, 2011 "Try Boys" (gay adult-youth) September 12, 2011 "Sissyboy Scenes" (gay adult-youth) September 19, 2011 "Sissyboy Matchup" (gay adult-youth) January 11, 2012 "Sissyboy Fixup"(gay adult-youth) January 18, 2012 "Sissyboy Adultery"(gay adult-youth) February 12, 2012 "Sissyboys in Love"(gay adult-youth) February 20, 2012 "Sissyboy Lust" (gay adult-youth) March 24, 2012 "Sissyboy Siblings" (gay adult-youth) March 27, 2012 "Sissyboy Test" (gay adult-youth) April 24, 2012 "Sissyboy Culture Shock" (gay adult-youth) May 24, 2012 "Sissyboy Honeymoon" (gay adult-youth) June 27, 2012 "Sissyboy Discipline" (gay adult-youth) June 29, 2012 "Sissyboy Physical Education" (gay adult-youth) October 4, 2012 "Sissyboy Humiliation" (gay adult-youth) January 23, 2013 "Sissyboys Caught Kissing" (gay adult-youth) April 11, 2013 "Molested Sissyboys" (gay adult-youth) May 3, 2013 "Constitutional Sissyboys" (gay adult-youth) May 23, 2013 "Sissyboy Stepmother" (gay adult-youth) February 19, 2014 "Sissyboy Beauty" (gay adult-youth) March 13, 2014 "Sissyboy Playdate" (gay adult-youth) September 16, 2014 "Sissyboy Empathy" (gay-adult-youth) October 7, 2014 "Virtual Sissyboys" (gay-adult-youth) April 2, 2015 "Sissyboy Panty Party" (gay-adult-youth) April 16, 2015 "Sissyboy Conversion Therapy" (gay-adult-youth) May 20, 2015 "Sissyboy Transition" (gay-adult-youth) June 3, 2015 "Sissyboy Spunk-up" (gay-adult-youth) June 26, 2015 "Sissyboy Satisfaction" (gay-adult-youth) July 8, 2015