You Bet Your Ass! by Throne (Patreon)
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You Bet YOUR ASS!
By Throne
© 2019-2020 QoS Comix All Rights Reserved
No part of this publication may be reproduced, distributed or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law. For permission requests, email to Devinwhitegurl@gmail.com
This is a work of fiction. Names, characters, places, and incidents are a product of the author’s imagination. Locales and public names are sometimes used for atmospheric purposes. Any resemblance to actual people, living or dead, or to businesses, companies, events, institutions, or locales is completely coincidental.
YOU BET YOUR ASS by Throne
Billy considered the clothes hanging in the spacious closet in front of him. He fingered the fine material of several shirts. Of course, the bar they hung from was lower than was usual. That was because Billy himself was shorter than most men. He was a jockey, so he had to keep his weight down, too. It made him self conscious to be out among tall people, which was one reason he had used much of the money he earned from being at the top of his field, as well as what he had gained from investments, to buy his impressive sprawling home. The other reason was that he liked to jealously hide his wife away from other eyes. Billy and Tatianna had been married for nearly a year now. Her height was superior to his by a few inches. He didn't mind that because of her sweet face and stunning figure. Long blond hair framed soft features and pouty lips. Though she was trim, her bust and bottom were plumped up. Billy loved that about her. Sometimes he would just gaze at her generous curves while she moved around a room. Simply being in her presence got him aroused.
The way she affected him wasn't a problem. Tatianna was always available for sex. There was plenty of foreplay, with her catering to his desires, and he would mount her eagerly, to release the tension that built up inside him. What he didn't notice was that she was always somewhat distracted. And that she never had orgasms. He knew that his penis was on the small side but just figured that size didn't matter, so long as you had technique. Unfortunately for his wife, he lacked that too. For her it was a mixed blessing that his shortcomings included a lack of staying power. He always finished too soon. But because his dick was too small to satisfy her, she was happy to get everything over with sooner rather than later.
Sometimes while they were in bed together she would remember her former life. Tatianna had been an exotic dancer at a wild club in a rough part of the city. She hadn't minded that guys drooled over her and got free with their hands. They were also very free with their tips, and she adored money, loved spending it, even recklessly. Besides, if a guy got to grabby with her, the club's owner would step in and take care of him. Marquis was a tall rangy Black man with sharp features, his hair worn short and natural, who sported a neat mustache and soul patch. The way her looked after Tatianna had always made her feel grateful and attracted to him. They had been more than friends for nearly a year before she met Billy and saw his impressive home and two cars, along with all the other trappings of the fancy life she had long craved. As much as she hated to leave Marquis, she couldn't say no to the jockey's lavish lifestyle. And he couldn't turn down her seductive charms and irresistible body.
Billy's mind drifted as he laid out clothes on the bed and then went into his private bathroom. He looked over the many products he had lined up on shelves. Billy was fastidious about his grooming and meticulous about his soft blond hair. He plucked his eyebrows, but just enough to keep them neat. Because a shiny nose was unacceptable to him, he regularly used medicated pads to remove oil from that area. He had never had much facial hair and there had been even less on his body. Rather than have to deal with shaving, waxing or depilatories, he had opted to have laser treatments. All that hair had been permanently removed. He likened it to how competitive swimmers kept their bodies totally smooth.
The end result of all those personal choices was that he appeared less then manly. It didn't help the impression that he was also fussy with clothing and décor. Most damning, when it came to how he was perceived, was that his natural way of moving was delicate and suggestive of femininity. But because he made so much money for his employers, and was a celebrity in the racing world, and had a beautiful wife, he was sheltered from what many people secretly thought. Billy had it all. And to make his life perfect, there was a major race coming up that he expected to win. The horse loved to run, the track was a favorite of his, and there was just enough competition that he would still have to show a great effort, which reflected well on him. And then his life began to unravel.
"We need to talk," Tatianna said, one afternoon about a week before the big race.
She had on a tight sleeveless top with no bra underneath, along with slacks that looked like they were painted onto her plush bottom and shapely legs. Her small feet were shown off in high heel sandals. Tatianna even had her golden hair back in a long ponytail, which she knew Billy loved. His hope was that what she wanted to talk about was sex, because he was overdue and that made him antsy.
"Sure," he said, sitting on their ornate antique couch. He patted a spot next to him. "What is it, honey?"
His bride didn't put herself where he had indicated. Instead she sat on an expensive wingback chair across from him. Damn, but she looked delicious. Billy's confidence was high. He even felt good about where he was seated. The couch, like most of their furniture, had been selected partly because it was scaled for someone small like himself. Having to use full size furniture irritated him, especially when his feet almost but not quite reached the floor.
"It's about money," she said.
"That's not a problem," he assured her. "You handle the finances, so you know how much we have."
"That's the thing. We have a lot less than you seem to think. I had to cash in some of your investments. The improvements I've made around here added up. And you know I like to treat myself to a gift or two now and then."
He did know that she could spend money like it was going out of style. On the other hand, he hadn't been aware of her liquidating some of his investments.
"Well," he told her, not quite as confident as before, "I'm sure we're still okay."
"Not really." Her natural pout became more pronounced. "You see, the way you keep me cooped up her, I got kind of restless. Especially when you were out of town, teaching that horse or whatever."
"Training, dear. I was training the horse I'm going to ride. I mean, the trainer does most of that, but I was there to work with him and... But that's not important. What were you starting to say?"
"It's just that I get lonely and bored. So I went to visit my friend Marquis."
"You mean, from the club? Where you used to... dance?"
"Yeah." She smiled as if that was good news to her husband. But then her face clouded over. "And he let me do some gambling. And hooked me up with some people who could sell me jewelry at a huge discount. And then there was a car, which he lets me keep at his place." She paused to observe the sick look on Billy's soft face. "But mainly it's the gambling debts. I'm in trouble Billy. And I don't owe the money directly to Marquis. There are some bad people involved. So I need you to figure out how we're going to pay them."
Billy felt like the room was tilting. He couldn't believe what he had just heard. Though he was afraid to hear the answer, he asked her how much money she was talking about. When she told him he nearly swooned. His beardless cheeks got pink and then went pale white. He leaned back and put his hands flat on the sides of his face, making himself resemble a girl in distress. His wife watched silently. When she thought enough time had passed, she made a suggestion.
"What if you lost that race, Billy? I mean, if you bet against yourself and then, you know, sort of didn't win on purpose. Couldn't you make a pile of money that way?"
"I could, but it wouldn't be worth the risk."
"Are you saying that I wouldn't be worth it? Your own wife?"
"No. I mean, it's not like that. Think about how much I'd be risking."
"Why don't you think about what might happen to me if I can't cover my debts."
"But, if anything went wrong, I'd be ruined. I would lose everything."
"I know. So what you could do -- not that anything bad could really happen -- but just to make yourself feel better, you could switch everything over to my name. That way, if the plan hit some little snag, just in case, they couldn't touch anything because it would all be owned by me. After it was all over and everything actually did go right, we could just change it back. See? And if you bet enough, not only would my debts be covered, but we'd make a ginormous profit."
As awful as it had all sounded at first, he had to admit that it was a simple and almost foolproof plan. It would be easy enough for him to throw the race. There were at least three other horses in the field who had a chance of winning. And she was right about everything else. Tatianna wasn't usually that clever, though she did have a natural instinct for acquisition. He brought his head back up. She looked so ravishing, and dependent on him, as she sat there waiting for his answer.
"Let me think about it," he said. "I mean, I'll do whatever it takes to save you, darling."
"I knew I could count on you, lover. Just to be sure, though, we should take care of the legal end right away. You can tell your people that you're thinking of a new venture, so you want your assets in my name for right now. All your assets."
"Sure," he told her. "That makes good sense."
So they did that and he began running over in his mind, several times a day, how he would ride in the race. What he would do if there was no clear second choice to win, once they were moving. How he would get in the way of the wrong horse if it tried to take a lead. He also decided to commit completely, by betting every cent he could afford, and more. Why not? It was a sure thing, with him deciding the outcome of the race.
All the excitement made him even more horny than usual. Unfortunately, the same plan that had him aroused, anxious to release some of his excess energy in bed, had the opposite effect on Tatianna. She was too jittery to do anything sexual. Her explanation was that, even though she trusted the scheme, she was concerned about him, and his state of mind. He tried to make her see that all he needed was to empty his balls, but no matter how discretely he said it, she found some reason to demure, and it was always because of how much she cared for him. The added stress unnerved Billy, so much that he began to doubt his ability to throw the race without being detected. He decided that the only safe thing to do was to dope the horse. Not a lot. Just enough to insure that its winning advantage was reduced. He could do the rest.
The day of the major event came. There were endless television cameras at the track. Reporters everywhere. Even a drone hovering overhead. He asked for a moment alone with his steed, just so he could relax the animal, and that was when he administered the mild dose of the drug. They would test for performance enhancing drugs, but wouldn't do anything to check if he had tried to reduce its ability to run its best. He was soon at the starting gate. His bet was placed with a discrete bookie. Everything was ready to go.
The bell rang and they were off and running. Billy's mount, Fiery Fury by name, took an immediate lead. Soon, however, she tired prematurely as the drug did its work. He made a minor effort to keep her from overcoming the handicap, at the same time acting like he was trying to do the opposite. His plan had been to have her come in second, but she fell back to third. That might arouse some suspicions but not enough to matter in the end. He made sure the horse his money was on had a clear path to victory.
Afterwards, most of the attention went to the first and second place winners. He was asked what had gone wrong and just said that even the best horse could have a bad day. But then everything fell apart. Someone had tipped the authorities, during the race, that he was going to throw it. When they checked for the type of drug he had used, it was in Fiery Fury's system. A quick search of the stable turned up the hypodermic he had used, with his incriminating fingerprints on it. He was busted. But the bookie would still pay off, with all the money going to Tatianna.
When he tried to contact Tatianna about getting him a lawyer, she didn't respond. There was a brief day in court. Billy was sentenced to three years in prison. He couldn't believe it. His career was ruined. His only consolation was that his home and cars and remaining wealth, including the payoff from his bet, along with future income from his untouched investments, were all safe in his bride's hands. Thank goodness for that.
He was in a detaining cell, waiting to be transported to the penitentiary, when she came to visit him. Tatianna looked alluring in a fitted skirt suit, businesslike and yet super sexy. She had on a pillbox hat that added to the dual effect. Billy picked up the phone that would connect him to her. She gave him an encouraging smile as she sat down. Picking up the receiver in front of her, she held it slightly away from her mouth and ear, as if it might be germ-laden.
"Hello, Billy," she said, not sounding overly concerned. "It's so sad how you got yourself into all this trouble."
"I did it for you, darling," he insisted.
"Nice try," she told him without emotion.
He said, "I'm sorry I won't be around to take care of you."
She responded, "That's okay. Marquis will keep an eye on me. He put a big bet on the horse you made win, and cleaned up. I mean, you made him a rich man."
"But what... How did he know?"
"Wasn't I supposed to tell him? Sorry, dear. But it works out well, because he's offered to help me in any way he can for the next 36 months. While you're all locked up. With a lot of big sweaty men."
"What are you saying?"
"Just that I'll be thinking of you, Billy boy. I hope it won't be too rough for you, being the smallest guy in the joint. Having everyone else look down on you. And, you know, noticing how you're not exactly the macho type."
"I don't understand."
"Sweetlips. With your perfect haircut and sleek hairless body, plus the way you hold yourself and place your hands. I mean, people were always asking me if you were secretly gay. That is, when you didn't have me locked up at home like your private sex slave. That's such a terrible way to feel, as if someone is treating you like their property, and thinks they can paw you or get their cock I your mouth, or just bend you over and have their way with you, whenever it suits them. Now I won't have any of that. Not from you and your tiny dick. But what you'll be getting, well, I can't wait to hear all about it on visiting days. That is, if I'm not in my house, managing all my wealth and property that you so helpfully put into my name."
"That was your suggestion. And I'd be okay if somebody hadn't tipped the law about our plan."
"Your plan," she corrected. "And it certainly was rotten for whoever did it to screw you over that way."
The wheels in his mind were turning. He said, his words coming more slowly and with less force, "And you let Marquis know about the race."
Before he could accuse her or finish putting the pieces together, she got up and cradled the phone. He was still talking into his end when she made an air kiss toward the unbreakable barrier between them, turned and, giving him one more look at her fantastic rump, wiggle-walked out of the room. The guard assigned to Billy during her visit towered over the jockey, even after the little figure stood up.
"Damn fine woman," the official said with a grin. "I'm sure she'll behave while she's waiting for you for... how long are you in?... a year?"
Billy's narrow shoulders slumped. "I'll be there for three years."
The guard didn't bother to stifle his laughter. "Yeah. She'll wait for you, short stuff."
He gripped Billy's upper arm and walked him away from the visiting area, toward the pick-up room. All too soon a van arrived and Billy was hustled into it. There were already two convicts in there, both of them tough looking, one white guy with a shaved head and endless tattoos, and a hulking Black man with massive hands. They both scowled at him, making Billy avert his eyes and wish he could become invisible. Everything Tatianna had said was fresh in his mind. What she had implied dominated his thoughts. He had assumed he would be going to some sort of country club facility. Had someone pulled some strings to make sure he went to the hellhole that he now understood was his destination? And what would be waiting for him when he got there?
Billy was unceremoniously ordered out of the van and told to walk only between two close-together white lines as he entered the processing section of the imposing prison. He was dwarfed by the guards, who had been chosen partly for their size and strength, so they could deal with violent convicts when needed. But no one was concerned about handling any trouble from Billy. They smirked openly at the tiny man. The three prisoners were taken to a shower room and told to strip. Billy was highly uncomfortable being naked in front of other men, but he had no choice. When he was naked and everyone saw his lack of body hair and how small his genitals were, he became a laughingstock. He cringed and blushed as he moved under the hard spray from the showerheads, soaped up, and rinsed off. He had to stand in front of noisy hot air blowers until he was dry, with everyone's eyes on him.
At last he was able to escape that shame as the trio was taken to be given their uniforms. There was a convict in green, which identified him as a trustee, at a small window. The other two men had their sizes estimated by him and were given appropriate clothing -- baggy orange jumpsuits. Billy stood there, still nude, while they got dressed.
The white guy sat down and said to the jockey, "How about you sit on my lap and we'll talk about the first thing that pops up."
The Black con told him, "I'd rather you just got on your knees and sucked my cock. But I guess you'd like that, being a faggot and all."
Billy's voice quavered as he said softly, "I'm not gay."
The big man asked angrily, "Are you calling me a liar, boy?"
When Billy turned to the guards for help they just chuckled at his plight. He returned his attention to the Black man and was relieved to see that he had already lost interest. Then he checked the trustee to see if he was ready yet with a uniform for him. He handed something over and Billy was grateful that he would be able to cover himself. Then he unfolded it and saw that though it was orange, that was the limit of how it matched what the others had been given. Instead of being big and baggy, with long sleeves and legs, it was close fitting and had no sleeves and the shortest of legs.
The trustee smirked at him and said, "We were told you were coming and that you're too small for our usual... fashions. So one of the inmates, a fairy who has access to a sewing machine and supervised use of scissors, modified one for you."
"Who... who told you?"
The man in the window shrugged. "Don't know. Don't care. But whoever it was had your size. Maybe somebody who knows you personally. Anyway, you might want to get into that now. Standing around in the all-together in this place, especially if you're small and shave your body, isn't a great idea. That is, unless you enjoy being raped. Which from the way you act, maybe you do."
Billy put a forearm across his chest and the opposite hand over his privates. Then he realized that he was assuming a feminine posture of modesty. He put his hands at his sides but that was too shameful. So he quickly got into the clothing, inappropriate though it was. When he looked down at himself he saw his hairless limbs being shown off, his slender waist accentuated, and -- he could tell by putting his hands behind him and touching -- his pert bottom displayed by how the garment clung to it. Billy sighed and followed the other two cons to their next stop.
Here they were to have their heads shaved. The Black guy objected and was told that everybody got the same haircut. The white con was already bald, so they just went through the motions to be thorough. When it was Billy's turn, and he was in the barber chair with his feet hovering above the footrest, the con with the electric razor worked on the sides of his head but left the top alone. He used some type of spray product that he brushed through the longer hair that remained, covering some portions of his scalp but not all. When he was done, Billy got a look at himself in a mirror that was set in a recess in the wall, with bars in front of it. What he saw was a girly version of himself, with a cute, short-sided hairstyle, including streaks of red through the longer blond on top.
"I don't want to look like this," he told the barber.
"What? You wanted pink streaks instead of red? Hey, I can't cater to all you fairies who get into the program."
"Program?"
"Yeah. They have this deal where princess types like you get to play dress up, because it's part of your whatever. Your personality or something."
"But I'm not that way," Billy asserted, though rather feebly.
"You may not be now, but try telling me that in a week or two. Now move it, sugarplum."
Billy numbly followed the other two cons into the main cellblock. From the three tiers came hoots and hollers. Rough male voices called out lewd suggestions to him. They honestly did mistake him for a homosexual. How had he been entered into that program for prisoners who actually preferred to look this way? Who did that to him?
The three new arrivals were herded along by two guards, both of them so much taller than the jockey. The white guy and then the Black one were admitted to their cells. At the far end of the row a door was automatically opened and Billy was shoved inside. The heavy metal barrier clanged shut and he looked out through the bars at the departing officers. When he turned around to inspect the interior of his cell he discovered that he wasn't alone. There were two other convicts in there with him. Both of them tall and muscular. Both of them Black. One had a lean hungry look and lines razor-cut into his short hair along both temples. The other was bulkier, He had a shaved head and a thick mustache that turned down at the corners of his wide mouth and dropped to the line of his broad jaw. They inspected Billy as if he was a savory meal and they were starving.
"Hey," said the first one. "I'm Kendrick. What's your name, boy?"
"I'm Billy."
"No, your name is Sweetmeat. Right?"
Too scared to disagree, he squeaked out, "Yes, Sir."
"And I'm Turk," said the other. "Looks like you really are some sweet meat."
"I... I'm not..." Billy's mouth was suddenly dry. Speaking barely above a whisper he told them, "I'm not that way. I'm straight."
"Oh." Kendrick nodded. "My mistake. Guess we won't be able to do no sex stuff with you."
"Too bad," Turk offered. "I was looking forward to shoving my cock down your throat, for starters."
"But you ain't gay."
"Not a fruit."
"Can't call you Sweetmeat."
Billy managed a hopeful smile. "That's right, fellows. I'm married and everything."
"Got it," Kendrick said. But then his dark brow creased. "Still, we got to give you the test. I mean, that's the rules. Right, Turk?"
"Right, my man. Got to follow them rules."
"I don't..." Billy swallowed with difficulty. "... understand."
"See," Kendrick went on, "we got to be sure you're not one of them closet gays. Like trying to trick us. Saving your goodies for some other dudes. That wouldn't be fair to us two."
"Not fair," Turk emphasized.
"So we going to just do that little test. Won't take no time at all, boy."
"But I already told you..." Billy began. He stopped when his protest was answered with angry glares. "All right. I guess I can take your test. What's the first question?"
"It ain't like a school test," Kendrick told him. "More like a army physical. Got to check for the sissies. Cause you know there's some white boys, kind of like your own self, who got that gay thing going but don't tell nobody. They got the craving for it. Just give them a tickle, maybe let them get they hand on a big old Black cock, and it all comes out at once. All of a sudden it's gay time for them. Can't keep their mouth off the jungle jawbreaker."
"Right," seconded Turk. "That African ass buster."
"So you just relax and let us check you out. That way we can tell all the other dogs you ain't no fag."
"If you pass the test."
Billy felt queasy. Being locked in a cell with two aggressive Black men was a nightmare. Still, if he just let them do what they wanted now, and they saw that he was straight, the rest of his stay would be less threatening. Once the word got out that he wasn't interested in guys, he would be safe. So he reluctantly decided to endure the next few minutes, or slightly longer, and then move on. Tatianna was probably already working to get him released. He felt confident that her attitude during that visit had just been from temporary upset.
"All right," Billy said quietly. "If you have to."
Kendrick sat on the lower bunk and patted a spot next to his hip. The jockey unhappily sat alongside him. The Black man set his hand on Billy's thigh, which was left bare because he'd been given that abbreviated uniform.
"Damn," Kendrick marveled. "It's just like touching a girl. Yo, Turk. Check this out."
The other man sat on Billy's opposite side and began rubbing his other thigh. Kendrick's fingers slid up under the barely-there leg of the shorts and brushed Billy's penis. Turk gave the warm flesh under his hand a few squeezes.
"So soft," Turk observed.
"Right," Kendrick confirmed. "And check what's between his legs. Or maybe what's NOT there. See if you can find anything, man."
Billy squirmed as Turk wriggled his fingers around under the shorts, feeling the jockey's crotch. This was beyond humiliating but he felt utterly trapped.
Turk said, "There's hardly nothing in there."
"We got to do a visual inspection," Kendrick decided, breaking that last word into three distinct syllables.
The two Black men pushed Billy back and moved him around without much effort, so that he was lying stretched out on the bunk, on his back. Kendrick told him to lower his pants. Turk leaned in with a hard look on his face to back up the order. The smaller man sniffled as he elevated his hips and got his fingers under the waistband of the modified garment. He eased it down, hoping one of the others would tell him to stop. But they let him bare his pale body below the waist. Turk gave the shorts an extra tug to drag them past Billy's knees, beyond the helpless con's reach.
Kendrick swore colorfully. "This is bad. Real bad. A small dick is a sign of being a pansy. And one this tiny, it's like nothing I ever seen. I mean, I've had some small-dick white boys when I was on the outside. They get a look at the bulge in my jeans and follow me around with they tongue hanging out, they so hungry for Black beef. So right now it's looking like our Billy belong on the pink side of things."
"That be tough for him. But let's be sure, man. How about we check his prison pussy?"
"Good idea, my brother." Kendrick put his forefinger in front of Billy's mouth and ordered him to, "Open up and suck this. Get it good and wet."
More afraid than ever, Billy nevertheless parted his lips. Kendrick didn't insert the finger, so the jockey had to prop himself up on his elbows to get it into his mouth. He rubbed it with his tongue, gathered saliva, and gave a few sucks, as he had been instructed.
"Holy crap," Kendrick remarked. "This one's got a natural born talent. Trying to get my finger in deeper. It's like a reflex with some white boys. Stick something stiff between they lips and -- whoop! -- they be getting greedy with it."
"Thinking about how they wish it was your cock," Turk suggested. "And dreaming like your balls are on their chin."
"Truth. So now we got the baby dick and the suck action. That's two strikes. This boy's ready to go for three."
He popped his thick finger out of Billy's mouth and got his hand under the jockey's bottom, feeling between his buttocks. The tip of the finger found Billy's rosebud and began to press against it. With a sob, the victim reflexively clenched his sphincter.
"Now he's showing me how he wants something inside him, so he can give it a rump hug. Wants to milk a Black tool with his back door muscles. Weak everywhere else, but strong right there."
Turk offered, "Probably got regular exercise back there. Work them muscles of love so they'll fit like a glove."
Both men laughed. While Billy's attention was on their words and their amusement, he relaxed just enough for Kendrick to detect it. That was when the big man drove his finger in up to the first joint. Billy wailed and writhed. Before he could recover, another third of the digit entered him. And while he was trying to catch his breath from that shock, it was plunged the rest of the way in. He was impaled on Kendrick's finger, which was moving in an exploratory way. The man who was jabbing Billy nodded to his Black cellmate and Turk grabbed Billy under the knees to raise his hips. He held him securely while Kendrick began working a second finger into that tight entrance. Billy cried out. In the adjoining cells, other inmates smiled at what they knew was happening.
"Please," Billy blubbered. "No more. It hurts too much. I'm not gay. I have a sexy wife. You can stop now."
"Can't stop in the middle of the test, Billy boy. You nothing but a creampuff. White and soft." He got the number two finger all the way in, sending Billy into a fit of trying to squirm free. Turk held him firmly in place white Kendrick added the end of a third finger. Before he went any further he cautioned the jockey, "You got to calm down or I might do some damage. I don't want to hurt you, little creampuff. I'm trying to help you out. Let you find out who you for real are."
"Aw, come on, dog," Turk said to his buddy. "You like it when they be thrashing around."
"How you can say that, my man? I got the boy's best interests in mind. Now let me get one more finger in his butt hole and we can get the test done."
He jammed the last digit in brutally, hurting Billy on purpose. The helpless jockey began crying uncontrollably. Kendrick kept his fingers moving around slowly inside him. When Billy had recovered enough to understand what was being said to him, Kendrick spoke again.
"I can tell that you enjoying this, Billy. Maybe not all the way, cause you fighting it, but I know a sissy ass when I feel one."
Turk wanted to know, "So he score three-for-three on the test?"
"Exactly. We got us a cock sucking boy right here. Real handy to have around when you want a blowjob."
Billy was still in constant movement, but now it was in slow motion. And despite trying to keep silent, he was mewling. He even began to push his bottom back against Kendrick's busy fingers. Worst of all, when Turk lowered Billy's legs, everyone saw that he had a hard-on. It might just have been from having his prostate stimulated, but neither of the Black cons was going to allow that excuse to be mentioned. They kept reinforcing the idea that Billy had been a sissy all along, and their efforts had brought it out into the open. Kendrick finally withdrew his three fingers and wiped them on the front of Billy's humiliating version of prison wear. He snarled at the newly arrived inmate to get on his knees. When Billy tried to at least pull his shorts back up, Turk barked at him to leave them where they were. So the jockey found himself kneeling in front of Kendrick with his bare ass exposed.
"Now," the leering man said, "get my pants down, creampuff. Do it."
Billy numbly obeyed. His bottom hurt and he was whimpering. He tried to think clearly but the pace at which everything was happening, along with the thought that he might actually be gay, reduced his mind to a mass of swirling confusion. Kendrick raised his hips just enough for Billy to tug down the seated man's loose trousers. What Billy saw when he did that made him freeze. Confronting him was an enormous cock. Dark, with a bell head. Thick-veined. Heavy balls partly visible under its wide root. He was so close that he couldn't help breathing in the masculine musk from the exposed crotch. That tube steak was at least a foot long and it was still flaccid.
"Well?" Kendrick asked. "Are you just going to make love to my Jones with just your pretty blue eyes? Or are you going to get them dainty white hands on it?"
"I... can't."
Turk interjected, "That's okay, Pinky. We just turn you around and use the other end. You probably like it better that way anyhow."
"What?" Billy's nose was running. "That would be rape."
"Yeah," Turk agreed. "But don't say it like that's a bad thing. I know you want it up the poop chute."
"No I don't."
"Yes you do. So unless you want to fight about it, you better agree. I'm saying you like to suck cock. And you want your ass raped. Ain't that so?"
Billy was caught in a cruel trap. If he stood by his assertion, Turk would punish him physically. But if he reversed his position and said he wanted that terrible act performed on him, they might do it.
"I..." The little man had to hope for the best. "I was wrong. I misspoke. What I meant to say is that I like..." He gagged. "... using my mouth on men. Like you. But I also enjoy it when they..." He started blubberingly wordlessly, then got it under control. "... when big men get behind me and... use me... sexually."
"You got to be clear, boy," Turk urged. "Got to say it so poor stupid folks like me, who ain't rich and smart like you, can understand. You got to talk like you on the street, Pinky."
"Yeah, creampuff," Kendrick said in support of his cellmate. "Say it plain. Let's hear it without the polite shit."
Billy understood what they wanted. He choked back more tears and managed to struggle through, "I love to suck cocks. Big Black cocks. But I also love to have them... shoved up my ass... and to be thoroughly... reamed by them."
"I don't know about that ream thing, but if you mean fucked, then okay." Kendrick nodded. "Glad you being honest with us. Now we can make your wishes come true. Get busy with my meat. Hands and mouth. Otherwise, it go in the out door."
His whole body trembling, lips quivering, Billy got his unsteady hands on Kendrick's enviably large cock. It took almost no encouragement to make it rise. Very soon, with Billy massaging it with both palms, it had gained several inches. The kneeling man goggled at the 14 inch monster he was expected to use his mouth on. He extended his tongue tentatively and touched the underside of the shaft, tasting the saltiness of perspiration. Then he kissed it, his heart racing. Licked it from base to corona.
Turk helpfully said, "You got to swirl around the head, punk. Round and round. Pretend like it's candy."
"Right," Kendrick agreed. "A all-day sucker."
The Black guys chortled at that term. They each held up a hand and slapped their palms together. Billy tried to do the tongue rotation, but found that the knob of that weapon was so big he could only do it by getting his lips around the bulb. He did that and found his mouth stretched wide to accommodate such a massive member. His tongue circled the widest portion of the business end, making the recipient moan with pleasure. Billy closed his lips and sucked, eliciting another approving sound. He couldn't force any more into his mouth, so he slurped up and down the length, got it wet, and then pumped it unhurriedly with his hand, the knob stretching his jaws again. He couldn't believe how it filled his gob, pressing his tongue down under its bulk.
Sitting next to Kendrick, Turk lowered his own pants. He snapped his fingers in front of Billy's eyes and pointed to his waiting Black cock. The jockey turned his eyes up questioningly to the man he was fellating. Kendrick gave him a lopsided smile and told him to go back and forth between them.
"It'll last longer that way, sissy."
So Billy began on Turk, who immediately wanted his balls licked. His cock rose to nearly the dimensions of Kendrick's. Billy mouthed it and lavished attention on it for about five minutes, until Kendrick flicked the small man's ear and signaled for him to shift back to his previous object of affection. The jockey edged to the side on his knees and resumed pleasuring the first cock, kissing it all over, slobbering on it, fondling it, and then kissing his balls too, without being told to. For a very long hour the hapless cock slave worshipped both dark rods. He would massage one while gobbling the other, taking as much into his mouth as he could before it made him gag.
Kendrick told him, "Don't worry, creampuff. We'll get you past that choking thing. Ain't got nothing but time in here. And the both of us going to want it from you every day."
Near the end, Kendrick instructed Billy to keep the head of his cock engulfed while pumping the shaft with both hands. He complimented Billy again on how soft his palms and fingers were. It made the jockey think of all the skin products he had used. That made him wonder if maybe he honestly was gay, just a little bit. The seed they had planted in his mind was growing already. Billy sensed that Kendrick was getting close to ejaculating. He dreaded having the man's sperm in his mouth. Kendrick growled deep in his throat and his hips jerked. Suddenly Billy's mouth was flooded by thick salty spunk. He fought to swallow it all, though the act was repellant to him. Some oozed out of the corners of his mouth but he gulped down the majority of it. Kendrick made him milk the last of it manually and not swallow it. Billy had to open his mouth wide and display what lay in it and coated his tongue. Not until both men had taken a good look was he permitted to ingest it.
Then he had to get back to Turk's rigid tool. This time he was able to get an added inch into his gullet, hardly gagging at all. Turk made a joke about him being a fast learner. Kendrick said it was the short man's gay instincts taking over. Every time Turk was close to spurting, he made Billy change over to lapping his heavy balls. At the same time, he had the diminutive jockey professing how much he adored eating cock. He told Billy to address him as 'Sir' and to sound more girly whenever he spoke. So Billy would bring Turk to the edge and then have to tongue his scrotum while telling him in a lisping whisper what a good time he was having. At last, with Billy's hands vigorously working up and down, his mouth wide, the head of Turk's cock resting on his lower lip, the second man blasted out his load. It hit the roof of the jockey's mouth, puddled under his tongue, overflowed down the back of his throat, and made him feel like he would drown in it. Billy eventually gulped it all down and then spontaneously used the end of his tongue to retrieve the clear fluid that followed that orgasm, gathering it as each drop appeared from the pee slit.
With Billy's oral virginity taken, his cellmates moved on to the next phase of their plan for him. It took place three times a day, when they went to the cavernous dining hall. After Billy sat down with his tray in front of him, he had to turn to whoever Kendrick had arranged to have sitting on his left. The convict there was always Black and from the loosely structured gang to which many belonged.
Billy was expected to act effeminate and use his overly swishy voice to whisper something to his neighbor like, "Hello. My name is Pinky. May I please suck your cock?"
It was all prearranged. None of the sex starved men said no. Billy had to slide down under the table, lower their pants, and give them a long, sloppy BJ. It had to be drawn out for most of the lunch hour. At the end, after he'd gotten a mouthful of thick slimy spunk, he was permitted to get back on his chair and have his meal. It made him nauseated to eat with the strong taste of male cream on his tongue. And because he didn't start his food until the period was almost over, he had to wolf it down. Someone else always got his dessert.
Kendrick and Turk made sure they always let Billy know how much his effort had earned them. It might be a candy bar or four cigarettes. That made him feel worthless, as well as further breaking down his male ego. He had to walk with a wiggle and use overdone gestures, always with limp wrists. Everyone who saw him assumed he was gay and he was beginning to imagine it was true himself.
They had other ways of demeaning him. He was too short to use the stainless steel urinal mounted to the wall of their cell. So they would make him drop his pants and one of them would pick him up and sit him on the cold metal. He had to hold his little prick down and pee into the bowl while they stood there mocking him.
"Bet you have to be careful on regular toilets, so you don't fall in."
"You look real cool there, boy, with your junior size feet dangling down."
At last it was time for his first visit from Tatianna. What Billy wanted to hear was some good news. She hadn't seemed eager to help him earlier. He credited that to the shock of what was essentially her plan, necessitated by her financial irresponsibility, going awry. In the time since then, he told himself over and over, she must have come to a more realistic view of the situation and made moves to help him.
When he got to the visiting room he was nervous. Happily, it wasn't one of those with a wall down the center, plexiglass windows, and communication only by phones. It had been painful during the previous shared time, when he had to speak with her under those circumstances. Now he was seated at a plain table, in a chair that was bolted to the floor, and there would be guards watching them the entire time, if not in person, then remotely. He wished he had something different to wear. Someone had ordered several more outfits just like the first one. And his hair still had that unwanted look.
He was thrilled when the door opened and in walked Tatianna, as beautiful as ever in a slinky black dress and some flashy new jewelry, her hair in a new style. But then she was followed by Marquis. The two of them sat down across from him.
His wife opened right up with, "You really screwed yourself, Billy baby. And it's been awfully inconvenient for me. I mean, I had to wait days before some of your accounts were unfrozen. But once they realized that all the money was in my name alone, everything was fine."
"But what about getting me out of here?"
"Why? Haven't you been eating well?"
He didn't even want to touch on that subject. And he would have preferred to avoid what his cellmates had been doing to him, and making him do with other convicts. But she seemed oblivious to his plight, so he had to say something. He would just be discrete.
Billy told her, "I'm being mistreated. By the men sharing my cell." When she just looked at him blankly, he went on, "They've been touching me. In inappropriate ways. And making me... do things for them."
"Oh," she said with a smile of understanding. "Those two big Black studs you're locked up with have been making you suck them off. And having you go down on their pals in the dining room at mealtimes. So that answers my question."
It was his turn to wear an uncomprehending expression. He said, "I don't understand."
Tatianna clarified, "I asked if you were eating okay. But that sounds like you're doing fine. Getting plenty of protein." She gave him a broad wink. "Fresh from the source."
"You don't understand," he said desperately.
"Of course I do, you loser faggot. You got yourself put in here. I'm on the outside with the money and house and cars that used to be yours." She shrugged. "What's so hard to understand?"
"I... I..." He implored her, "You have to get me out of here. I want to come home. And be with you."
She made a face and said, "Ugh. Why would I want you back? You were never a good lay, with your miniature puppy dick and under-two-minutes performances. Besides, now it turns out that you're a flamer. I'm infuriated with you for lying to me about your sexuality all that time."
"I'm not gay," he protested for the umpteenth time.
"No, you're just sucking every cock you can find because it's your hobby. Oh, please, Mary. Your Man Card has been revoked."
"You can't leave me here."
Marquis broke in with, "She can and she will. But don't worry. I'm there for her. Spending lots of time together. Making sure she gets all the attention she needs."
"I don't want my wife with another man. Especially a crook like you."
"Who's the crook, creampuff? You're locked up and I'm running free."
"Bu... but, she's my wife," he spluttered.
"I know, man. The separation and divorce can't be until later, after she makes sure she has every last penny of your money. But hey, we've got three years."
Tatianna added, "That's plenty of time to make sure everything is legal, Pinky. Speaking of which, I gave my consent for you to go completely into that program where you're allowed to dress girly all the time. They needed me to tell them that you really are a freak and love to be in panties and stockings and whatever."
"But I've never been like that."
"Sure you have. Maybe what you've been eating has messed with your memory. Of course, I've been getting a lot of that, too, and it hasn't bothered me."
"What do you mean?" he demanded, not sounding as forceful as he meant to.
"She means," Marquis said, putting his hand on Tatianna's, "that I have my big Black cock in her mouth all the time."
Tatianna expanded on that with, "When it's not in my pussy, which is a lot."
Billy though he was going to swoon. He brought his hands up and fluttered them under his chin, his mouth opening and closing soundlessly. The body language Kendrick and Turk had insisted on was taking over. Even Billy's voice reverted to its higher feminine register and softer girly speech.
"I can't go on like this. Those big men are being brutal to me. They do such terrible things. Can't you talk to them?"
He was addressing his wife but it was Marquis who answered. "I have been talking to them, along with a bunch of the officials here, creampuff. Are you so stupid you can't figure anything out? Your hot wife and me made sure you got fucked over, and that I ended up making a killing on that race you threw, and you signed everything over to her before you did it. Now my contacts in this place are making sure you don't give us any trouble -- ever."
The jockey was stunned. He stood up and began swaying. His small hands gripped the edge of the table. Tatianna left a business envelope in front of him. She turned to Marquis, who took her in his arms and kissed her passionately. The big man's dark hands roamed freely over her body and she ground herself against him. Plainly, she wanted all she could get of his sexual prowess. She even grabbed the considerable bulge in his pants. Billy's knees gave out and he collapsed back into his seat.
His wife stepped away from Marquis and said, "Have a nice night, Billy. I know I will."
Marquis grinned wolfishly and told their victim, "I'll pass the word along that you're real in touch with your gay side. And that you're ready for a complete prison honeymoon."
The two of them linked arms and strolled out of the room. The Black guard came in. He must have heard and seen everything. He also must have been part of the effort to ruin Billy.
There was a grin on his dark face as he said, "Damn, boy. You really threw it all away."
He grabbed Billy's bicep with a vicelike grip, snatched up the envelope, and marched him out of the room. A second guard took over at the entrance to the cellblock, accepting envelope, and returned him to Kendrick and Turk. They were waiting with sadistic anticipation. As soon as he entered the cell, Billy saw why. Lying on the lower bunk were new items for him to wear. Obviously they were from that program he had been unwillingly put into. There were pink panties and fishnet stockings, along with a pair of glossy red heels. There was even a belly shirt, bright scarlet, with the word SLUT across the front in swirling letters of garish yellow.
"Let's go," Kendrick said. "We can't wait to see you in your new look, creampuff."
"Do it, Pinky," seconded Turk.
Marquis and Tatianna had used those same names for him. The two of them must know every detail about his plight. Billy blushed bright pink as he got out of one shameful outfit, preparing to don something even worse. He pulled the panties up his slender legs, feeling their silkiness against his hairless skin. Then he rolled the stockings, the way he had seen his wife do, and sat to unroll them back up. Finally he got into the clinging top and slipped his feet into the heels. Turk made him strut around, wag his bottom, and assume a series of erotic poses.
He swore volubly. "You looking better than before, Pinky. Kind of like a walking invitation to get busy. Know what I mean?"
"And," Kendrick added gleefully, "we got the word that, now that your wife has the money deal worked out for certain, we can go ahead and make sure you never think you're a man no more."
Billy crossed his arms over his smooth chest, looking quite girly. He squealed, "No more. I'll call the guard."
"Thanks for the reminder," Kendrick told him. "You owe that dude a BJ. But later for that. Right now we got to pop your cherry. How about you get my cock all ready for the big event?"
"Yeah," said Turk. "And after he's done with you, that pretty mouth will be on my Johnson. I get sloppy seconds on your cute ass."
"But before you wrap them lips around my love muscle, use some of this."
Kendrick tossed him a tube of lipstick. It was magenta. Barely able to keep his hand steady, Billy applied it to his mouth. Kendrick said the clumsy way he did it made him look like a cheap whore at the end of a long night.
"But that's okay, girl. I like that look. And it helps that we can see your itty bitty dick through them panties. Really makes it dirty to know we're going to be slamming a sissy."
Turk said, "One who still don't admit he's a pansy, and that he secretly want to get drilled. Even that it will turn him on."
The two men converged on their vulnerable prey. They roughly got him on his knees. Kendrick slapped his face a few times. Then Billy had to describe one of his spit-heavy blowjobs, along with plenty of dirty talk about how he loved doing it and how, for the first time, he was ready to go all the way.
"Use me now," the kneeling man said, making it sound sincere. "My ass needs your big Black cock in it, Sir. Please don't finish in my mouth. You have to deflower me."
"Have to what?"
"Bust my cherry, Sir."
"I'll bust your damn cherry. Then I'll bust my nut. Leave a big mess of scum all up inside your tail. That'll make you a full time, no-turning-back, fag sissy. Right, creampuff?"
"Yes, Sir. Thank you, Sir. That's what I want."
"Pretty freaking funny, too. You being married to this super babe."
He held out a picture. The second guard must have slipped him that envelope. Billy saw an image of his wife and Marquis, side by side, in front of the bed at home. Both of them were naked. The Black man's cock hung down an impressive length. The jockey tried not to compare it to his limited endowment but couldn't control what he was thinking. The next shot Kendrick showed him was of Marquis with an incredible erection, at least as big as Kendrick's, if not larger. Tatianna was on her knees, caressing it, white hands standing out against rich brown skin. Then he was shown another, of the two of them in bed, Marquis happily thumping her pussy, she with her head turned so her face was toward the camera, wearing a blissful look. She was giving Billy the finger.
As if under a spell, Billy took Kendrick's cock and tenderly coaxed it to full size. It didn't require much coaxing. He gave it some extra personal treatment with his mouth, adding plenty of the lewd talk the man liked to hear. It was almost as if Billy were seeking revenge on his wife by pleasuring the man standing in front of him. He brought Kendrick to a peak of excitement. The powerful man hoisted him to his feet, spun him around, bent him forward, and ordered him to keep his hands on the edge of the bunk. He was too low down so they put all their pillows under his feet to raise him enough for easy access.
"Spread them feet! I like how those heels make your legs look. Now get them panties out of the way. And that ass is just begging for my cock. Isn't it?"
Sounding more girly than ever, Billy assured him, "I can't wait. Please fill me up, Sir. I want you in me."
Inside he was scared half to death. And afraid of being damaged back there. Plus, he didn't want further confirmation that he might be gay. But his cellmates had him so well conditioned by then, and what his wife and her lover had said was so unnerving, plus those pictures had so rattled him, that Billy didn't fully understand how he felt. When the end of Kendrick's cock made contact with his pucker, even though that was all that had happened so far, Billy began to weep. The Black man spit into his hand and rubbed saliva on Billy's tightness, even poking a slippery finger inside him. Then he held the jockey's hips and pressed himself against him so that the head of his cock stretched Billy's hole and slid past the ring. It hurt Billy but also stimulated him.
Kendrick said, "The race is on, girl. Number One is Big Kendrick, riding Creampuff. He's driving through the pack." He jammed several more inches inside. "Running hard." Sank himself almost all the way in, making Billy wail and shed hot tears. "And taking the lead." He plunged in up to his root.
Turk called out, "Ride him, brother."
The Black man behind Billy pulled partway out and slammed all the way back in. He did it over and over, his lust mounting. Billy blubbered and cried. Kendrick dug his fingers into Billy's soft hips. The penetrated little man grew less vocal. Kendrick moaned. Billy sighed and gasped. The two of them fell into a rhythm as Billy shoved back to meet each thrust. Kendrick's long strokes had his partner squealing. The sounds Billy made turned into words.
"Don't stop," Billy shouted. "Please. Sir. I don't know what's happening to me. Just ride me. Ride me hard."
Turk ducked down to check between Billy's legs and, sure enough, his laughably small pecker was hard. Whether he wanted it or not, he was responding fully to having his ass ravaged. When Kendrick heard that, he varied his pace to keep the jockey stimulated without making him finish. Billy got frustratingly aroused. His balls hadn't been emptied for so long. He was frantic to find release. But with expert control, Kendrick denied him that necessity. The Black man, however, after nearly 60 minutes, staged a final ferocious attack on the defenseless rump and blasted his load deep inside. He didn't pull out for long minutes, while Billy stood there, with his excitement momentarily subsided, wracked with shame.
Then it was Turk's turn. He had Billy pull up his panties. Cum leaked from his bung and made an embarrassing wet spot. He had to lie on the lower bunk on his back, legs bent up and feet against the wall. The bare edge of the frame dug into his neck as he hung over it, holding on to the thin mattress with both hands. Turk knelt. Billy's head hung level with Turk's crotch, upside down.
"Look at that mouth," Turk said with a devilish glint in his dark eyes. "A perfect cock socket. Just right for some face fucking. And Pinky's lipstick got messed up, so she looks extra trampy. Heh."
He took Billy's head between his broad hands and held it there while he rubbed his cock on the jockey's face. As he started to get hard, Billy caught the bobbing end between his lips and sucked on it with his eyes half closed, like it was a hot afternoon and he had a popsicle. Turk began to slide it in and out, setting off the gag reflex but not choking him. On the second and third tries, the jockey was able to take it in the throat with increasing ease. Billy hung in that uncomfortable position while Turk had fun with him, twisting his ears and adjusting his head to different angles. At last he was ready for the main act and pulled the small man down, got him onto the floor on his hands and knees, and put himself behind him. Kneeling there, Turk lowered Billy's panties and took a minute to enjoy the feel of that hairless body under his hands.
He got ready for deep penetration. Billy didn't act as reluctant this time. Turk put the mushroom head of his tool in position. Kendrick had provided plenty of natural lubrication. Turk grinned to himself and then shoved in hard, burying his monster organ in one savage thrust. Billy screamed but the sound was choked off as his assailant set a furious pace, humping him like some rutting animal. He kept it up for a solid ten minutes. Turk wasn't in the mood for long-and-slow. He wanted his payoff right away. He took ramrod, punishing strokes, really working that tight passage. Billy was crying but everyone could hear the whimpers of satisfaction that were mixed in with his wails. The Black man grunted, paused, and then finished with a flurry of action that triggered his reward. He hosed Billy's innards with his semen. At the same moment, the jockey was pushed past his limit and fired a full helping into his panties. Now they were soaked front and back, from both Kendrick's leakage and Billy's own discharge.
After gaining a rush of relief, and while Turk was still inside him enjoying his afterglow, Billy was again overwhelmed by shame. They had made him enjoy it. He was being turned into a cock addict. He hung his head and sobbed loudly. Even so, he was still tingling from what he had undergone. He didn't know how much more they might be able to change him. Turk finally withdrew. Billy was permitted to raise his wet sticky panties. The jockey clenched to try to prevent more dribbling.
"Damn, girl," Kendrick said. "Your puny dick sure creamed that girly underwear. And I know your ass is ready to drop more mess from what we put in here. So let me help you."
He picked up Billy and set him ignominiously on the urinal. The jockey shook his head, not wanting to be made a spectacle like that. Anyone walking by could witness his disgrace.
Turk said, "Just like a king on his throne. Or maybe a queen."
"More like a princess," suggested Kendrick. "Princess Panty Messer. She can just stay there all night, so she don't get no spunk nowhere."
"But I got to take a piss."
"No problem. Just aim between them pretty legs. Try not to hit her smooth bald dick area."
Turk chortled as he stepped up and pointed his tool. He let loose a thick, strong smelling, stream of urine that hit the bowl and splashed up against the seat of Billy's panties. Then he wiped his cock clean on the insides of the jockey's thighs, above the stocking tops.
"I got to drain the dragon, too," Kendrick announced.
He replaced Turk in front of Billy. Got his cock in his hand. Started to piss and intentionally hit the front of Billy's already unclean panties. He drenched the small man's genitals through the thin material and left them dripping. The acrid smell of urine assailed Billy's nostrils. He sat there feeling miserable.
"Aw," said Kendrick. "You all sad, creampuff? Wait until you been up there a few hours. That'll give you something to feel bad about." He chuckled. "But at least now that we visited your back door, it ain't like there's anything worse we can do. Right?"
Billy brightened. "That's true. I mean, what could be worse than what you already did?"
"Truth. It's not like we'd make you hold our balls in your mouth."
Turk added, "Or have you use that talented tongue between our butt cheeks."
"And even up in our asses."
"Especially when we're all sweaty and got the stank back there."
Kendrick followed that with, "And I'm sure we wouldn't use your mouth in place of that piss pot where you're sitting, if we didn't feel like walking all the way across this cell."
"Wouldn't never," agreed Turk.
"Unless we felt like it," Kendrick pointed out.
"Which we probably would."
"Definitely would, cause that's just what you do when you got a sissy."
Billy shuddered. He knew it was all true, and everything they had just said would happen to him. Besides which, he had a strong premonition that they would think up many other indignities to inflict on him, a succession of horrors with no end. That set off a cascade event in his mind, of helplessness and the desperate desire to please these men who absolutely controlled him. Three years was going to be like a life sentence for little Billy the jockey. He had bet his ass and lost, so now somebody else owned it.