Sam was the first one out. His chips ran dry two hands later and he didn’t attempt to barter clothes for the opportunity to stay in the game, as if anyone would have offered. When Tegan had played flirtatious games of strip poker in high school the usual rule was that if you weren’t playing or naked you had to leave the room, but Tegan imposed no such rule here. For one, Sam had already seen her naked on countless occasions. Secondly, she wanted him to continue to observe.

A few hands later Trevor lost the last of his chips but traded Tegan’s shoes to Jayden for fifty and rallied back from the brink.

After that Tegan lost again.

“It seems that I will be keeping your foot claddings.” Jayden mused. “Though I have to say I do not think I have much use for them myself. Not my size.” He grinned at her.

“You’re not really going to keep them are you?” Tegan pouted.

“To me they are worth a hundred dollars, I accepted that risk.” Jayden shrugged.

“I have a hundred seventy five right here.” Matthew patted the pile of frilly garments in his lap.

“The game continues for now, of course, but someone will hold these items at the end of the night, and you are out of means to bargain, are you not?” Jayden hinted.

He’s bolder than I expected Tegan thought.

“Maybe” she said aloud, glancing at Sam. He watched passively, with the demeanour of a man who no longer has a horse in this race. “Maybe not.”

“You have an alternate proposal?”

Tegan’s mind raced with possibilities as she tried to sort out the details. Her mind was fuzzy with the bottle of wine she’d consumed but things were more or less according to plan. This was her moment. Sam had no leverage here and she was going to exploit his jealousy to humiliate him in front of his friends, even knowing that tomorrow she would still go right back to the natural order of him fucking her as much as he wanted, and the giddy thrill had her brimming with excitement.

“Here’s my suggestion.” She leaned across the table, leering at Jayden with what she hoped was a smouldering gaze gaze. “I earn my clothes back from you,” Tegan turned her head to Matthew “and you.” She looked back to Jayden. “Then when we’re done, you let me back in the game. Give me a new set of starting chips. I play sitting in the lap of whoever’s chip leader, and winner take all.”

“What does winner take all mean?” Trevor queried, obviously wondering what the draw was for him, since he currently held none of Tegan’s clothing.

“If I win, I take the money, and my clothes. If I’m not, the winner gets me, any way they want, for the rest of the night.” She glanced at the purse. “Plus the money, I guess.”

There was a moment of silence while that sank in. Jayden was the first to recover.

“Ok, but first things first. How do you plan to earn back your clothes.”

Tegan fixed him with her green eyes and ran her tongue around her lips.

“Now?”

Tegan didn’t bother wasting more time with words, instead she slid off her chair and crawled under the table to Jayden and proceeded to unzip him and take out his cock. He was already hard and probably had been for a while given that he started seeping precum as soon as she engulfed his swollen circumsized head in her mouth. Given that he was basically a stranger she was taking a small disease risk but he seemed clean and healthy, so didn’t see the harm. She looked up at him as she blew him as he locked eyes with her, her mouth working his head and shaft. She didn’t concern herself with her audience, having grown accustomed to people watching. In fact it was something of a break for the others to just watch her work compared to what she was normally subjected to. Occasionally she took her mouth from him and ran her lips up and down the underside of the shaft but mostly she took him in her mouth and throat while gripping the base of his cock with her hand, using the heel of her palm to massage his balls. After a few minutes of activity Jayden began to grunt and she felt his balls tensing under her hand so it was clear he was going to blow. Knowing she still had a long night ahead of her she did him the courtesy of allowing him to cum in her mouth, which she graciously swallowed without hesitation. His spunk was thick and tasted slightly beery, which made sense all things considered.

Jayden sagged into his chair with relief after blowing his wad and she crawled out from under the table next to him, delicately dabbing at the corners of her lips. She picked up his half-finished beer and downed the rest of the bottle to wash down his sticky load, glancing at Sam. He remained strangely placid, apparently having no thoughts to contribute on this matter as he took a slow swig of his own beer.

Tegan set the bottle back down on the table then turned to Matthew, placing her hand on his shoulder as Jayden tucked his dick back in his pants.

“Ready?”

“What do I get?”

“What do you mean?” Tegan enquired innocently.

“Well, technically you own me one seventy five, so…”

“You think deserve a better reward?”

“Well, yeah.”

“I’ll give you two options.” She paused while she considered what those options would actually be – she was kind of winging it “…either you can fuck me – with a condom – til you cum. OR… I can blow you and you can cum on my face, and I’ll wear it until the end of the game.”

Matthew thought about it for a second then said “I really think I wanna fuck you.”

Tegan circled around behind Matt and took his hand to pull him to his feet, then sat on the edge of the table where she had been seated, the section that was most devoid of chips. She took the apron from him and retrieved a condom from one of the pockets, tearing the packed open.

“Pull your dick out already.” Tegan commanded, pulling him close with her free hand. When he complied she rolled the condom awkwardly onto his stuff cock. He wasn’t big, maybe below average length but normal thickness. Or maybe it just seemed that way because of his slight chubbiness. Once she was satisfied the rubber was secure she leaned back on her elbows and invitingly spread her legs for him, revealing her little pink slit. “Fuck me, stud.”

Matthew didn’t hesitate a second. He stepped between her parted thighs and lined his cock up with her slit, groaning as he sank into her warm depths. She wondered if he had sex often, if her snug pocket would bring him off quickly or if she was in for a long ride. Because she had offered herself as a reward for a well-played game of poker this wasn’t about her, she was simply content to receive him inside her until he came.

At one point Sam got up and walked away announcing that he needed to piss. Jayden and Trevor were more than happy to watch her get fucked. After couple of minutes some heavy panting and a strained groan signaled the arrival of Matthew’s orgasm and he drove his cock as deep into her as he could as he twitched and spasmed inside her. She could feel the heat of his seed trapped by it’s thin latex shield and they stayed locked together like that for a minute until Matthew withdrew, holding the condom as his cock slowly wilted. He pinched off the soggy rubber and tied a knot in it, awkwardly leaving to dispose of it in the kitchen. Tegan glanced over and noticed Sam has returned, with yet another beer. Maybe it helped dull whatever pain he was feeling.

Tegan gracefully ease herself down off the table while Trevor and Jayden tidied up the slight mess of scattered chips and cards created by the brief fuck session. She noticed that her leaking juices had left a small stain on the tabletop but whoever owned the table was not complaining. Matthew and Jayden retook their seats, Trevor hovered awkwardly for a moment as if expecting something, slightly slow to recall that without holding any of the garments he had no bargaining power. Tegan scanned the chips in front of each player and settled gently into Trevor’s lap. The bulge in his jeans was more than apparent under her ass.

“You seem to be the current leader.” She whispered.

“I intend to keep it that way.” Trevor responded, as he counted out a hundred dollars worth of chips from the bank and Matthew began to deal the cards.

“I assume all you gents are disease free.” Tegan queried. There was a round of nods and affirmations. Tegan continued. “New rule then. Because I care so much about your health and wellbeing, and because I think it will keep things interesting.” She shifted in Trevor’s lap and unzipped his fly, taking out his cock. Feeling it grow in her hand once free of his pants she was reminded of its impressive size. The monster at the glory hole had been bigger, but not by much.

“When I saw I will play from your lap, I mean ON your lap.” Trevor did not resist as she spread her lower lips with one hand and guided his cock inside her with the other, slowly easing down until she felt his cockhead pushing against her cervix. She settled into a delicate balance impaled on his shaft with a gentle moan. Trevor groaned in response as her tight walls gripped him.

“As a reminder of what you stand to lose… no cumming. You can choose to pull out, but go off accidentally and you’ll be disqualified from the game and from the prize. Fair?” There were no objections and Matthew dealt the next hand.

Perched on her pedestal of Trevor, Tegan was finding it hard to focus on the game. Sam was staring off vacantly, not even bothering to voyeuristically enjoy watching her share herself with three of his friends, which was kind of driving her crazy in and of itself, but mostly she really wanted to fuck. Matthew’s short lived effort had done nothing to ease her needs and all she wanted to do was start fucking herself on Trevor’s massive prong until she came. It didn’t help that Jayden was staring at her splayed lips split open by Trevor’s tool, possibly transfixed by the sight being the only person who hadn’t had a chance to sample her pussy yet.

Apparently Trevor was having trouble focusing as well. He lost the next two hands and his chip lead to Matthew who was already hard again and keen to wear her pussy bareback for a while, groaning as Tegan settled onto his lap.

“No cumming” she reminded him and he nodded dreamily.

“Can I feel your tits?” he enquired keenly.

“Sure, touch me wherever you want. Just don’t cum.” Tegan insisted as Matthew’s hands wandered up her body and caressed her small breasts, playing with her nipples. She was so preoccupied with paying attention to his cock inside her to make sure he wasn’t about to blow his load again that she didn’t pay attention to her cards and bet badly. Matthew was presumably similarly distracted and at the end of the hand Jayden held the chip lead. She eased off Matthew’s lap and headed over to Jayden, who pulled out his mostly hard cock again, holding himself as Tegan lowered herself into his lap. Jayden was a good size but compared to Trevor she could receive him more comfortably, and he didn’t also seem like he was on the verge of blowing. As much as her pussy was aching with a need to really get fucked, she was in a better position to focus on the game. She had decided she wanted Trevor to win, probably before she even bent the rules to feel him inside her again without him winning, and was trying to figure out how to make that happen. She supposed that she could try to subtly disqualify Jayden but there was no guarantee. Thankfully she had a run of good cards and actually become the chip leader for the first time.

“I guess that means I sit on my own chair for a while. Sorry fellas.” She eased off Jayden and circled back around the table to retake her seat between Trevor and Matthew but the very next hand Matthew took the lead back after winning a huge pot. When she went to sit on him, Matthew adjusted himself so he didn’t enter her.

“Gotta concentrate.” He mumbled, apparently determined to go another round with her, but it didn’t help. Two hands later Jayden took the lead again and Matthew was out. Now she faced off against Trevor while nestled on Jayden’s prick, with Matthew sitting off to one side with his cock still out, seemingly optimistic that he wasn’t done using it for the night.

Tegan glanced at her cards and saw that she had a pair of fives. She also, from this vantage point, caught notice that Jayden had a lousy hand, a four and a seven, which she assumed he didn’t know she saw. The flop was a four, an eight, and a king. That meant she had her pair of fives, and Jayden had nothing but a pair of fours. If Trevor had even one king or eight, he’d win the hand. She wondered if there was any way she could signal Trevor this without outright saying anything. She bet aggressively and pushed Jayden’s bet higher and Trevor called at each step. She didn’t know if he had a good hand or if he sensed something from her but eventually Trevor went all in, as did she. Her breathing deepened and she felt her pussy quivering with anticipation as she looked forward to Trevor winning and her changing places again. She played the next card: another eight. That gave everyone a pair of eights in addition to whatever else they had. She held her breath as she turned the last card to reveal: a four.

Fuck Tegan swore internally. That gave Jayden a three of a kind! In fact with the eights on the table it was a full house, a decisive win unless Trevor had something excellent. Trevor sagged in his seat and that told Tegan everything she needed to know: he was holding nothing. Jayden apparently realized this as well and flipped his cards over to reveal his full house, then immediately he groaned and she felt his cock twitch. Tegan jumped off his lap just as Jayden began to spurt, desperately trying to block it from hitting the table with his hands, grabbing napkins from the table to clean up the mess.

“Shit!” he exclaimed.

Tegan circled around the table and held onto Trevor’s arm.

“Sorry Jayden, looks like you’re disqualified.” Tegan said with forced disappointment.

“But I won!”

“I never revealed my cards. The game wasn’t over.” Trevor shrugged as he swept the cards into a pile. “So I guess we’ll never know.”

“You prick, you know I won!”

“Sorry Jayden, don’t be a poor sport. Those were the rules.” Tegan said. Jayden looked to Matthew, who offered no sympathy. He looked to Sam, who looked amused for the first time the whole evening but otherwise remained silent and passive on the issue.

“Well fuck you guys!” Jayden put his dick away and went to the kitchen to wash his hands.

Tegan turned to Trevor.

“Well, you get me all to yourself. Are you ready to claim your prize?”

“I am.” Trevor said, taking Tegan by the hips and setting her on the table.

“You… don’t want to go to my room? Somewhere private?”

“Nope.” Trevor said simply as he placed his hand on her chest and pushed her back, taking her thighs in his hands and pulling her hips up to his cock, laying his meat across her pubic mound, his cockhead almost reaching her navel. “I think I like the idea of them getting to watch me plough the daylights out of you.” Trevor said as he drew his hips back, lining his cock up with her dripping gash and pushing the head inside. “After all, I’m pretty sure that’s what you really want, isn’t it?”

With that last word he pushed his cock deep inside her, Tegan let out a cry of pleasure as he bottomed out, his meaty knob pressing up against her cervix, thankfully not bashing it. Obviously he knew her limits and didn’t plan on hurting her. Once he had buried himself all the way in he began to thrust, bringing out just a little of his length before slamming back in, holding her by the hips to keep her in place as he pistoned her love tunnel at a steady pace. She bit finger finger to stifle her cries of excitement. Being absolutely ravished like this with an audience of near strangers was something new and despite her earlier boldness, she felt pangs of humiliation set in. Jayden was standing in the doorway of the kitchen, still transfixed by her reddened pussy lips as Trevor rocked in and out. Matt was using her panties still clenched in his fist to jerk himself off as he watched her little tits bounce back and forth on her chest. She turned her head the other way to look at Sam and for the first time since the game started she locked eyes with him. She knew, in that instant, that all of his frustration and annoyance had faded away. As much as she’d played him, thinking that by giving him what he was too afraid to admit he wanted from her, that she was dominating him by making him look weak, he had gotten exactly what he wanted out of the night. She strongly suspected that once Trevor was done with her he would want to climb into bed with her and pump her full of seconds, to reclaim the hole that he felt rightfully belonged to him.

She was snapped back from her reverie, her back arching as she let out a louder moan. Matthew was cheering Trevor on as he jerked his cock and Jayden was still watching in apparent silence, perhaps still seething with jealousy that his victory was snatched away. All of a sudden her body began to tremble and Trevor started thrusting faster sensing what was happening. He placed one hand on her pubis and found his clit with his thumb, nestled down in her slit as he continued to pound her little cunt. As he started rubbing her nub with his thumb she began to quake and she let out a guttural scream as Trevor’s relentless fucking pushed her over the edge and kept her rolling. She tried to push his hands away but she couldn’t stop him fucking her until eventually he began to slow and the aftershocks of her orgasm faded away. She lay there fore a moment catching her breath until she became dimly aware that she hadn’t feel him shoot. She looked up at him towering over her and down at his still erect cock standing proud and glazed with her juices. There was a moment where realization dawned and she started to shake her head in protest but he was already upon her. He took her by the shoulders and flipped her over, pushing her face down into the table, pinning her with a hand on the back of her neck. With his other hand he pushed against one of her ass cheeks to expose her little starfish.

“Wait, no.” Tegan protested, trying to struggle.

“You don’t mean that.” Trevor said bluntly as he fished in the pocket of her apron where she had gotten the condom for Matthew earlier. He found several single-use sachets of lubricant. “You knew this would happen.”

“Please, I don’t think I can. You’re too big, please.”

“I do love hearing that.” Trevor said as he ripped the sachet with his teeth, keeping Tegan pinned, then squeezed the contents onto his fingers. With his slimy fingers he added some lube to the head of his cock then pushed a slippery finger inside Tegan’s ass. She let out a groan as she felt his digit penetrate her and start to spread the lube around.

“To be completely honest, I’ve never done anal before. Most girls get one look at me and won’t even consider it. But I think you’re different, Violet. I think you’re a special kind of girl, who’s willing to try just about anything.” Trevor let the words hang in the air, keeping his finger inside her but also not taking things further. He was giving her time to decide. Tegan knew if she absolutely refused, he wouldn’t go ahead with it. But much like all the other things she had unexpectedly gone through with lately, she didn’t want to say no and waste an opportunity.

“Go slow.” She whispered, eventually. Matthew let out a cheer as Trevor withdrew his finger from her anus and replaced it with the tip of his greasy cock. Slowly he pushed against her little backdoor and she whimpered as she was forced to open. She wanted to relax but she was having trouble not visualizing his cock stretching out her little pucker. As much experience as her roommates had given her with anal, this was next level.

Suddenly she felt a change in pressure as his cockhead slipped inside her, the mushroom flare opening once it got past her outer ring and she whimpered again knowing that there was only one way this experience was going to end for her now. Trevor gave her a moment to adjust before proceeding, easing more and more of his cock up inside her. She kept whimpering, tears prickling behind her eyelids feeling every centimeter of him push past her hole and into the velvety softness of her rectum, felt every twitch of his body against the tight muscular ring of her anus as Trevor adjusted to this new experience. Eventually and surprisingly she felt his crotch press right up against her cheeks and realized, as Trevor groaned with satisfaction, that he must have managed to get that massive thing all the way inside her. She tried to imagine how it fit, then regretted it. She tried to image the state of her butthole, like someone stretching out a rubber band and the mental image made her tremble.

“Tell me when you’re ready for me to move.” Trevor said gently, not wanting to ruin the magic of the moment. Tegan took a while to respond, but eventually she nodded and Trevor slowly pulled out before sliding back in. Her ass ached, but it wasn’t burning. Despite his size he was probably the gentlest she’d had to date, and appreciated the consideration. Gradually, taking cues from Tegan’s responsiveness, Trevor began to pick up the pace. He seemed to enjoy taking long steady strokes. She couldn’t imagine how much of him he was drawing out of her before re-inserting it because it was too unfamiliar to tell, and she was used to Angus’ style, a selfish hammering of his glans in and out of the ring to blow his load as soon as possible. Trevor seemed to really want to fuck her as deeply as possible, exploring her to a depth no one ever had or likely would again. She slid her hand under her hips and found her clit with her fingers, rubbing herself. She wasn’t aiming to have an orgasm but felt that stimulating herself might make it easier to manage, but to her shock even a light touch of her clit sent a ripple of pleasure through her. Without realizing it, her body was right on the edge. She felt her muscles clench and Trevor groaned in response as her asshole squeezed his cock. She suspected he wasn’t far off either and decided that if the only way forward was through, she was going to get him there as soon as possible.

“Fuck my ass.” She whispered. Trevor leaned down over her as if to hear her better.

“Say that again.” He grunted.

“Fuck my ass.” Tegan repeated, a little louder and more urgently as she started frigging her clit faster. “I want to come when you do, you better hurry up.”

Trevor needed no more invitation than that. Tegan nearly regretted her decision and let out a mixed cry of pleasure and pain as Trevor started fucking her faster. He still insisted on pushing himself in deep and began using small strokes but instead of just battering her hole, he kept pushing all the way up inside her, her ring dragging back and forth against the hilt of his cock. She moaned, circling her clit with her finger tips, panting and trembling as Trevor announced with a groan.

“I’m cumming.”

“Me too…” Tegan said with a strained voice. She let out a startled cry as her orgasm released at the same time Trevor buried himself all the way inside her. She heard Matthew grunt on her left, presumably blowing his load as he jerked off into her panties. Somewhere deep up in her guts she felt the mini explosion of Trevor’s ejaculation, his hot cream pulsing along his shaft and draining into her bowels. Trevor held still and she thought she could still feel him emptying himself inside her as her own orgasm shuddered slowly to a halt. As she lay there just breathing she felt Trevor’s wilting cock pull out of her ruined hole and he backed up a step or two, sinking on weak knees into his chair. Tegan just lay there, feeling cool air on her aching ass. She wasn’t sure if that was lube or spunk leaking out of her but it felt unsettling. She felt thoroughly violated, and vulnerable, and on top of taking a huge dick in her ass she had an audience to watch it happen. She tried to imagine how she’d have felt about this a month ago and almost laughed out loud to think about how far she’d come in her depraved adventures. She started to gently ease herself off the table, gingerly climbing to the floor as if worried she might turn inside out. A dizzy spell hit her as the wine she’d drunk over the course of the game caught up with her.

“I think I need to go lie down.” She said weakly.

“Oh, but we aren’t done.” Sam said. She lifted her head to look at him blearily. “In fact the night is young, and I’m pretty sure these guys are good for another round.”

“The game’s over.” Tegan said, confused.

“Sure, the game’s over. But today is a new day. And I haven’t had my turn.”