Tiffany sat at the table with four of her boyfriend’s father’s buddies in nothing but her sports bra and bloomers. She had never been so uncomfortable in her entire life as each of them openly looked at her body, a couple of them actually rubbing their crotches. Attracting the attention of men was not something new for the young cheerleader, but she had never been made such an obvious sex object before. Glancing up at the door she wondered where Mr. Taylor had gone. It was a small mercy, but she was grateful he was not here to see her predicament.
Ted Taylor could, in fact, see her predicament from the chair in the darkened hallway that he had been tied to. When it became clear that his buddies were cheating her at cards he had tried to intervene and been beaten and restrained. Now he sat in the hallway outside his den, a dirty sock stuffed in his mouth, able to witness the scene playing itself out in his own study. This was his fault, he never should have allowed Tiffany to sit down for a hand or two. He had known his friends were dirty old men, but it had never occurred to him that they would try to take advantage of a sixteen year old girl; his son’s girlfriend, no less.
Roger was the ringleader, of course. He could not believe how stupid this girl was. She had sat down with nearly three thousand dollars in cash, talking about how she was going to buy a car in the morning. They had let her win a few hands, and then just slowly took it away from her. Whenever he saw her waver, he gave the signal and she would be winning again. The chick had actually started to cry when she was out of money. That prick Ted had tried to put a stop to it, but he was easily subdued. He wished he could have seen Ted’s face when he had told Tiffany he would buy her cheer uniform for five hundred dollars. He wondered if Ted’s cock was as hard as his was when she tearfully pulled that tight sweater off over her ample tits.
Daniel had seen Roger do a lot of down and dirty things, but this was a new low for the group. Sure, they had gangbanged more than a few lonely skanks they had picked up in bars and slipped roofies to, but this was different; this chick was sixteen years old! Any real reservations he had disappeared when her large breasts bounced into view. Even contained in her restrictive sports bra they were gigantic; full and round like cantaloupes and her nipples were rock hard from the cold air. She was his daughter’s age, but all he could think about was slipping his dick between those mounds of flesh until he shot a load of sticky jizz all over her beautiful face.
Felix had no problem with what they were doing to this little hottie. He knew how cheerleaders were, bouncing around, teasing everyone and then only hooking up with the most popular guys. They inevitably grew up to be snobby housewives who continued teasing dudes in the neighborhood with their tiny tennis outfits as they jogged. Maybe she was a sweet kid right now, maybe she was already a heartless bitch, but either way if he got his chance he was going to put his dick in her; if she happened to hate it – so much the better.
George was the only guy in the group who actually knew this girl. His daughter was one of her best friends and she had slept over at his house countless times. He remembered when she had started developing breasts and the first time he had jerked off from the other room while watching her prance around his living room in her little flimsy pajamas. In his mind he had already fucked her in every possible way. If Roger pulled this off, he was going to make her look him directly in the eye when he penetrated her. He wanted her to never forget how he made her feel when she came over to the house.
Tiffany was still crying a little as the game went on. She should leave, she knew, but how was she going to explain to her parents that she had lost all of their money in a poker game? They had scrimped and saved for months so she could get a car, and her father had sold his precious motorcycle. If she didn’t find a way to get the money back, she was going to break their hearts, she would undoubtedly wind up grounded which meant no prom, and she’d still have no car and no way to get a summer job! At this point she had no illusions about what these men wanted from her. In the best case scenario she was going to expose herself, in the worst she was going to have to have sex with them. Tiffany had never done either with anyone before, not even her boyfriend Jim. It was unthinkable, but yet she continued to play poker – unable to hide her bra clad breasts because of the cards in her hands. She was stuck and all she could do was hope her luck turned and she could start winning.
Ted had never been so frustrated in his whole life. Straining against the cords that bound him to the wooden chair produced no slack. He tried to call out, but the sock only permitted him to make a feeble groan. Worst of all was the pain of his engorged cock trapped in his jeans. He had always struggled to keep from lusting after his son’s girlfriend. When they had first met she had been an awkward pre-teen, cute but definitely a kid. Over the past couple of years, however, she had blossomed into a walking wet dream. Her tits just kept expanding, stretching out all her shirts, filling every v-neck with impossible cleavage, and always bouncing on the sidelines! Tiffany’s ass was equally as voluptuous, shaping her jeans and doing the most amazing things with the pleats in her skirts. And the girl had always been adorable; full pouty lips, dazzling green eyes, and long curly brown hair that reached to the small of her back. Somehow he had always managed to get the impure thoughts out of his head when she was around – she was likely going to be his daughter-in-law after all – but no matter how much he willing himself to do so now he just kept staring at her body, the tears and pouting only making her sexier.
It didn’t take long for Roger to cheat her out of the rest of her money. She collapsed into her hands, sobbing – certain of what came next. She wasn’t wrong, of course, although the exact particulars of Roger’s depravity were beyond her imagination. He explained to her that they were all going home unless she went into Ted’s private bathroom and used his vintage straight razor to shave her pussy bald. She would then take off her bloomers and bra and put on her cheer uniform and do a cheer for them. He passed a slip of paper to her with his idea of an appropriate cheer and her face fell. She couldn’t imagine doing this, but she also couldn’t imagine going home without her three thousand dollars. The men all sat, ogling her, smirking, and making her furious, but in the end it didn’t matter. They held all the cards. She sighed loudly to make sure they knew she wasn’t happy about it, and headed off to the bathroom, slamming the door. Tiffany had no idea how much hotter it was that she hated it.
He knew it was coming; Tiffany was going to get fucked the same way they had fucked so many other women over the years. Except she wasn’t drunk, or drugged, or even partially willing like those other girl’s had been. This was rape. She might be consenting because of her predicament, but the truth was she was being cheated. And, of course, she was only a teenager. If he had been able, he would have told her that he would give her the money, that she didn’t have to do anything she didn’t want to, but he was completely unable to help her. Adding insult to injury was the fact that he was definitely aroused by it all.
Tiffany cried hard while she lathered up her crotch and carefully removed all the hair in Mr. Taylor’s sink. No-one had ever seen her pussy, or her breasts, and she certainly didn’t want to remedy that situation with a group of horny old men. Her mind was swimming as she tried to think of a way out of this mess but no solution presented itself. She had two choices: leave and face the consequences or stay and hope she could somehow earn at least most of the money back without losing her virtue.
When the cheerleader returned to the room the men were all naked and every cock was pointing to the ceiling. Tiffany’s eyes were wide. She had never seen a man’s dick before and she certainly never thought she’d be seeing four at once. Roger laughed openly at her shocked expression as he slowly stroked his imposing tool. As much as she wanted to, she couldn’t look away from it – it was as thick around as her wrist and nearly as long as her forearm! Did they really get that big? Felix was big also, but Dan and George were a bit more average. It didn’t matter to Tiffany, they all looked dangerous.
Roger cleared his throat and explained the situation to Tiffany, “Here’s the deal: tonight you are our personal plaything. You will do what you are told, without hesitation, and when we are done with you we will give you your money back. We are going to video tape the whole thing so we can relive it whenever we want. As long as you don’t tell your parents or try to lie and suggest that we have raped you or something, then that video won’t make itself to the Internet.”
“I – I thought I would do this cheer and then we’d play more poker?” Tiffany wasn’t exactly surprised by the proposal, but hadn’t expected it to be so definite so early.
“Well, we’re done playing poker. This is the only offer we have for you. If you don’t like it, get out of the uniform you sold me and get the fuck out.”
Tiffany knew she didn’t really have a choice. This was a nightmare, but she was going to have to endure it. They had moved the poker table aside, and as the men masturbated the sophomore cheerleader went into her act. She had a couple of false starts after which Roger explained that she better put her all into it or the deal was off.
Cheering with no bra was painful for the girl, but the men were loving watching her heavy udders bounce under her sweater. When she kicked her legs high, they all got glimpses of her freshly shaved snatch and her plump ass. Roger had her shaking her rump like in rap videos and all the men cheered. Daniel was capturing the whole thing on Ted’s video camera. She cheered according to the script, “Gimme a C! Gimme an O! Gimme a C! GImme a K! What’s that spell? Cock! What do I want? Cock! Gimme a cock!” Never had she been so humiliated but no one cared – she was just an object of their desire.
When she was done she stood there panting while George pulled her sweater off over her head. Suddenly she was being groped from every angle. Roger was sucking on one of her nipples and Daniel was on the other. She had never felt anything like it, the scruff of their faces on her skin, the tickling of their tongues on her sensitive nubs, the bite of their teeth. It wasn’t unpleasant, except that it was disgusting and demeaning. George was kneeling behind her, his face buried in the crack of her ass, licking her up and down and occasionally forcing the tip of his tongue into her asshole. She tried to move away, it was horrible, but he held her hips tightly preventing her escape. Worst of all was Felix who was passionately exploring her mouth with his tongue while fingering her pussy with his index finger. She didn’t kiss him back, but he didn’t seem to care.
Ted watched helplessly from the hall, seeing the abject horror on her face as the men mauled her perfect body. She put up very little resistance and the video camera was capturing every minute of it. He wanted to help her, to let her know he’d give her the money and she could just run, but there was nothing he could do. Even if he could get free he wasn’t entirely confident that he wouldn’t just join in on the fun – his dick was certainly ready enough.
Tiffany had touched herself from time to time, but never really masturbated because she always felt so guilty about it. No-one had ever seen her naked before. No-one had ever touched her so intimately. The girl was in turmoil, both by the shame she felt for allowing herself into this situation and the pleasure the men were bringing to her body. She couldn’t understand what was wrong with her; she shouldn’t be enjoying this, but her body was not listening to the outrage of her mind and emotions.
After several minutes of being groped and licked, Roger pushed firmly down on her shoulders and Tiffany sank to her knees while the men surrounded her. Everywhere she looked she was face to face with cum dripping cocks. Fresh tears came to her eyes as she was instructed to begin jerking them off and she wrapped her little hands around her first male organ. She had always refused to give Jim a hand job even after they had gotten hot and heavy while making out. It was one thing to rub him a bit through his jeans, but only whores have hand jobs or blowjobs. Of course she had friends who did that, but she didn’t have to do that kind of thing to attract a guy. Jim knew he was lucky to have her.
The dicks were hot and hard and leaking fluids and Tiffany was horrified as Roger grabbed her hair and pulled her toward his cock, wiping it on her tightly closed lips. “Suck it, bitch!” he snapped, but she just shook her head. After a few moments of stabbing at her with his rod, he hauled back and slapped her. The pain took a second to register and Tiffany was stunned – no one had ever hit her before.
“You bastard! Only whores do that! I’m letting you grope me, I’m jerking you off! Isn’t that enough?”
These words caused a round of laughter, but Roger’s face was furious. He grabbed her by hair and pulled her toward him, shouting into her face, “We are paying you for this, slut! You are a whore. You are pleasing cocks for money. Now, you’re going to suck all of our dicks, and you’re going to get fucked in every way we can think of, and if you tell me no again then you can forget about the money and I’ll make sure this video gets sent to everyone you know.”
Tiffany knew she was beaten. She had no more resolve. Sobbing she grabbed Daniel’s and Felix’s cocks and this time when Roger pulled her toward him, she opened her mouth. It was so large she had to stretch her lips to get them around the fat purple head. He told her to spit on it and afterward she realized that it was easier to let it penetrate her mouth. Surprisingly she was able to suppress the gag reflex as Roger entered her throat, and to everyone’s amazement she took quite a bit of his cock. When her nose felt his pubic hair she realized that she had swallowed the whole thing, but her amazement was short lived as she began to panic that he wasn’t going to let her breathe. Frantically she pulled back, gasping for air, but then he was pushing it back inside again. Over and over he fucked her face. “Holy fuck you’re a good cocksucker!” he jeered at her and then began to cum. Tiffany realized he was shooting sperm into her stomach, just moments before he backed up and filled her mouth with his spunk. Intuitively she knew to swallow, that to spit would get her slapped again, but she wasn’t able to keep up and it came out around his dick and onto her chin.
Daniel didn’t give her a chance to recover before he plunged his own tool into her face. Compared to Roger he had a small dick, but it was still difficult for her to take deep in her throat. He made her stick her tongue out and lick his balls while he was buried in her mouth. After a few minutes he withdrew and had her hold her tits up while he slipped his dick in her deep cleavage. Tiffany hadn’t even heard of tit fucking but she caught on real quick. Her emerald eyes were like saucers as she watched the tip appear and reappear from between her mounds. She only had a second to react when she realized he was about to cum, it wasn’t long enough for her to avoid getting a face full of gooey man juice.
One eye glued shut, and covered in white spunk, Tiffany began bawling while the men laughed. Felix stepped up to the plate. Despite his raging hard-on, Ted cringed as Felix fed his enormous snake to Tiffany even while she shook from crying. His dick wasn’t as long as Roger’s but it was just as wide, and she was really working to accommodate it. He was brutal, grabbing her hair in a fist and slamming his meat into her again and again, ignoring her pleas and beating fists. When he came, he buried himself inside of her, shooting directly into her gut and not stopping until she milked every drop with the spasms in her throat. When he finally pushed her aside, she was gasping for air.
This left only George, her best friend’s dad. “Please, Mr. Stevens, I can’t take any more.” She eyed his throbbing cock warily, realizing he was not going to be deterred.
He was gentle, but he guided her mouth to his dick, “You can take it, honey. That’s a good girl, suck Daddy’s cock like a good little whore.” She couldn’t believe what she was doing! What would Candice say if she saw her dad right now? So many times she had looked up to this man, shared meals with him and his wife, trusted him, and now he was fucking her throat!
George didn’t take long. He had been fantasizing about Tiffany for years and seeing her covered in cum, diligently sucking his cock, was just too much! He came in her mouth, not caring that she let it all dribble out over her chin.
Tiffany lay on the floor, exhausted and humiliated, glad that the ordeal was finally over. Sucking cock was every bit as horrible as she had imagined, and she was as demeaned as she had thought a whore would feel. It never occurred to her that the men weren’t sated.
Again it was Roger who took the initiative. She felt him lifting her and then all of a sudden she was lying on her back on Mr. Taylor’s leather sofa. He spread her ankles wide and with one hand lined his dick up with her virgin hole. “Oh God, please no! I’m a virgin, you can’t do this!”
Roger pushed his massive penis into the inexperienced girl, probing for a couple of inches and then hitting the tight skin of her hymen. “Well, I’ll be damned, this slut is a virgin!”
“Let me see!” Daniel cried out, and as Roger stepped aside he slid his own head inside of her pressing against her hymen. One by one they all violated her cunt, no-one popping her cherry.
Roger grinned at her, “Okay, honey. If you want to keep your virtue we can live with that. All you have to do is beg me to fuck you in your ass.”
Tiffany’s heart plummeted. She had heard about anal sex, but assumed it was only something that crack whores would do. But she had never been so desperate before and she realized that this was a way she could maintain her virginity, although she doubted any man would want to marry her after this whole ordeal anyway. The idea of having her asshole violated was unthinkable, but she realized she preferred it to losing her cherry.
Roger watched as she worked it out. Of course she’d let him in her ass, she really had no choice, but getting up the nerve to beg for it was an entirely different situation. He was a bit surprised when she looked up at him, “Okay, you can do it.”
“I can do what, whore?”
“You know! You can have anal sex with me.”
“I told you to beg me to fuck you in the ass! Make me believe you want it and I’ll leave your cherry intact.”
If looks could kill Roger would have been riddled with bullets, but instead he simply smirked at the girl, his cock getting even harder as he saw the hatred in her tear filled eyes. “Fine! You fucking bastard! Go ahead! Fuck me in the asshole! Please, I need it! Please, please, please, put your filthy dick in my ass!”
Roger slapped her, and then without waiting for a reaction spun her around on the couch so she was on all fours. “You wanna be a bitch? I’ll fuck you like one!”
“Oh God,” Tiffany moaned as she felt the head of his dick at the entrance to her anus. She heard him spit and then felt it on her ass, he massaged it into her with the tip of his cock. When he began to push, she screamed. Ted began to struggle anew, hearing her distress, but he couldn’t do anything. From out in the hall he could only watch as Roger’s massive cock split his son’s girlfriend’s asshole open. “Oh fuck! You’re tearing me in two! Take it out! Fuck, stop it!”
Roger didn’t stop, he kept pushing inch after inch of his dick into her virgin asshole. Tiffany had never felt anything so painful in her whole life. Roger had never felt anything so tight; it was like a vice gripping his dick. She tried to pull forward, but he just followed, pressing her up against the sofa back and giving her no-where to go. Daniel and George watched in awe as the girl somehow managed to take his massive dick in her asshole. Finally he bottomed out, his balls pressing against her cunt. “Holy fuck! Please take it out!”
Pulling back, Roger allowed inch after inch of his dick to leave her asshole until just the tip was inside. Then he slammed it back in, making her grunt in pain. He did it again. “Beg me for it, whore! Tell me you love it!”
Tiffany didn’t love it. She didn’t understand why anyone would do this willingly. It was nothing but pain. “Oh God, please stop!”
Roger didn’t stop. He began fucking her asshole in earnest, telling her what a dirty little fuck she was, how incredibly tight her asshole was, and how much he liked seeing her take it. Her screams eventually devolved into full blown crying. She had already made him cum, so he was able to last a long time. After a while she began to get used to it, and when he reached around and began stroking her clit she gasped. The pain in her ass was intense, but combined with the pleasure coming from his finger she felt herself building up toward an orgasm. “No! Stop doing that! I don’t want to!”
But she was not in control. In her most humiliating moment so far, even enduring the worst pain of her life, Tiffany could not stop herself from cumming. Her whole body shook and tensed up, causing even more searing pain in her ass. “Oh Fuck! You bastard! Stop it!”
“The deal was that you beg for it, bitch! So I guess the deal’s off.” He pulled out of her asshole and with one stroke sank his shit covered dick into her now soaking wet vagina. Her hymen tore in two and every inch of his disgusting manhood sank into her virgin hole. Tiffany screamed, and it took a moment to realize that this new pain was coming from her now deflowered pussy. She was being slammed into the sofa time and time again as he gave Tiffany her very first fucking. Already on the edge, she couldn’t stop herself from cumming again. She hated herself and hated him, but it didn’t matter, her body was responding as if she loved it.
When he began to cum she first felt relief that it was finally over, but then it occurred to her that she was completely unprotected. A grown man was filling her fertile womb with baby juice! “No! Stop cumming in me! You’ll get me pregnant!” But everyone just laughed at her.
Roger pulled his dick from her, slick with her blood, shit, and both of their cum and grabbing her by the hair pulled her down onto the couch and shoved it into her mouth. She grimaced and struggled, but ultimately sucked his filthy pole clean. To her chagrin she felt it stirring again.
George was a bit upset with how selfish Roger was being taking both her anal and vaginal cherry, but hey, without Roger none of them would have had the guts to do this in the first place. He nudged his friend aside, and laid Tiffany on her back. “Look at me, honey,” he said in a kind voice. She looked up at him, her large green eyes wet and frightened. “I’ve wanted to do this for so long.” She felt his cock opening her sore pussy lips. “I always think of you when I’m fucking my wife. I think of you when I’m jerking off.” He began pushing into her and she looked away, “No! You look at me while I’m fucking you!”
Tiffany looked back at him, “I hate you! You’re a shitty father!”
“That’s right, baby. Take Daddy’s cock.” The hate in her eyes was inflamed as he slid his cock inside of her. He grabbed both of her tits and then began pumping her. “Rub your clit, my little slut. Help Daddy make you cum again.”
The cheerleader reached down between them and found her nub. It was incredibly sensitive and pleasure shot through her as she brushed it with her fingertips. Again, she couldn’t understand how it felt so good when every fiber of her being was screaming for it to stop. Looking into the face of one of her rapists, a man she had always trusted, she somehow managed to cum and cum hard. Midway through she felt him cum inside of her. It was surreal. She could be pregnant right now; pregnant with her best friend’s father’s baby.
Daniel took George’s place, but after a few moments decided to switch things up. He laid down on the floor and told Tiffany to straddle him. Far beyond really putting up any fight she obeyed, now actually fucking a man. She worked up a sweat fucking him, and to her horror found that she was on the edge of cumming yet again. Tiffany tried to think of something to distract her, anything to keep from being forced to cum again, but she couldn’t think of anything worse than the situation she was actually in and so it was futile.
Ted was going insane. He was caught up between being frustrated at not being able to help her and not being able to fuck her. When he finally got free he was going to kill Roger. Tiffany’s screams as she came again carried to his ears and it was as if the reverberations went straight to his cock. It was clear she was hating it, but there was no denying it that she was getting a lot of pleasure.
Felix was tired of waiting, so he got behind Tiffany and began pressing against her asshole even while Daniel was still fucking her pussy. That such a thing was possible, Tiffany had no clue, but the reality of her situation came home as she felt both of her most private holes being stuffed. Felix was huge, and it was painful, but the sensation was too much. She began cumming over and over, screaming, cursing, and begging them to stop. Roger filled her mouth with his semi-hard cock and she sucked it eagerly. Finally, after several minutes, they all came simultaneously.
At some point Tiffany had actually passed out. It didn’t stop them from continuing her assault however. George and Daniel both wanted a piece of her asshole. She would wake up to find another cock in one of her holes, or just long enough to take another load in the mouth.
Finally, they were done. Roger tossed her money at her, much of it sticking to the cum leaking from her various orifices. He dragged her over to the card table and tied her down, bending over it. Tiffany looked like a total whore; pleated skirt up around her waist, cum dripping down her thighs and chin, asshole gaping. As they left, Daniel tossed a pocketknife into Ted’s lap. “Thanks for a great party, asshole.”
It took nearly an hour for Ted to manage to get the knife open and to cut through the cords securing him. The whole time he heard Tiffany sobbing in the other room, begging someone to let her go. Finally he was free and he went into the room intending to comfort the girl.
“Please don’t tell Jim!” she cried when she saw me. “I didn’t want to do it! They forced me.”
Ted realized that she still had no idea that he had seen the whole thing. “Tiffany, I’m so sorry!”
“No, it’s not your fault Mr. Taylor! But please don’t tell Jim.”
“No, honey, I’m so sorry that I’m not strong enough to resist you. But I promise I won’t tell Jim if you don’t.” Ted finally freed his raging hard-on from his pants and without any further ceremony plunged it into Tiffany’s sloppy asshole. She was pretty loose, but it was still tighter than his wife’s pussy and felt amazing on his dick.
“Oh fuck! Not you too!”
Ted realized he wasn’t going to last long and his son would be home soon, so he switched over to her pussy amazed that it was nearly as tight as her asshole. He fucked her mercilessly, ignoring her crying and pleading. She did cum again, right before he filled her cunt with his baby juice. Tiffany sucked him clean gently, without having to be asked, and then he untied her.
He had expected her to attack him or something, but she just sat there, cum covered and softly crying. “You promise you won’t tell Jim?”
“If Jim never knows about this it will be too soon,” he said.
Ted left to go shower, and Tiffany went up to Jim’s room to clean up and put on some clean clothes. When Jim got home, she had managed to stop crying but he could tell something was wrong. “Just make love to me, Jim. I need someone to just love me.”
Jim couldn’t believe his ears. After two years of trying to get her to do anything, she was just giving it up. He found a condom and laid her down on his bed. It was gentle, and he kissed her and caressed her and told her she was beautiful. Tiffany loved it, and when he finally put it inside of her she liked the feeling. But after thirty minutes or so, she became aware that she was no-where near an orgasm. She just kept thinking about getting her hair pulled, her face slapped, her asshole fucked, and being called a whore. When Jim finally came, he rolled over and went to sleep.
Tiffany lay there trying to sleep for a while, troubled by the fact she was clearly a real slut. Finally, she sighed heavily and then crept upstairs to Ted’s room. She tip-toed into the room, careful not to disturb his wife, and whispered in his ear, “Daddy, I need you to fuck me so bad! Just fifty dollars and you can fuck me in my asshole again!”