Strip Poker Predicament

Holidaying Solo

After a day on the slopes, Kevin went to the hotel bar to see what the night life was like. It was the end of the first day of his solo skiing holiday.

Originally planned for himself and two of his friends, this was supposed to be a short break with a his mates to hit the slopes, have a few drinks and let themselves go a little. The others pulled out at the last minute after pressure from their other halves - pressure which single Kevin didn't experience - but they had already booked equipment and a hotel. The flights he could still cancel, but there was no way to recoup the other costs, so he decided to make the most of it and went on his own.

The hotel was clearly very busy as Kevin arrived and at check-in there was an angry couple with children in tow, demanding to know how their reservation had been lost. Offering to accept a downgrade to free up the large suite and resolve the situation, the hotel gladly accepted and got everyone checked in. The manager promised to have a word with the kit hire company and see what they could do about the extra equipment costs, and Kevin settled into his single room.

Collecting his skis, poles, goggles and lift pass from the hire company, he discovered the manager was good on his word and his friends' orders had already been taken care of. So, in the end it all worked out and Kevin had a good day on the slopes, getting in a good work out and enjoying the scenery. Away from the busier slopes the snow was dazzlingly white and the world was almost silent, and while he regretted his friends could not join him, he had appreciated the different character this holiday was taking.

The bar was busy, this being peak season. Kevin grabbed a beer and soaked up the atmosphere for a bit from a stool at the bar. Eventually a gesture from a nearby table caught his eye - three girls were waving at him, giggling and trying to catch his eye. He smiled and acknowledged them, and one of them waved him over, pushing a spare seat away from the table and inviting him to join them.

Taking his drink he stepped over, and said hello, introduced himself and in turn met Alice, Lucy and Deborah. "Sit!" said Alice, "Join us. How are you doing?"

They turned out to be a group of three friends on very much the same kind of holiday he had originally planned, had come to ski and let their hair down a little, maybe find some trouble to get into. They'd been there a few days already, but had a few days left before they needed to fly home.

Alice was clearly the leader of the group, leading the conversation and asking most of the questions. Lucy was very outgoing and a little bit tipsy, while Deborah was something of a quiet one preferring to listen rather than talk.

"We were wondering whether you wanted to join us for a drinks and a game of cards in our room," said Alice. "This place gets a bit too busy in the evenings for my liking, and it's much cheaper to drink upstairs."

Back to their Room

The girls had a big suite on the fourth floor, with two twin bedrooms and a small lounge area in between with couches and a table.

On the side were glasses and a few bottles of spirits. Lucy started lining up some shots.

"So, what are we playing?" asked Kevin.

"Strip poker, of course!" said Lucy, giggling. "We always play strip poker. Are you up for it?"

This seemed like a marvelous idea to Kevin, and he relished the thought of these lovely ladies taking off their clothes. He quickly agreed and they all got ready to play.

"Now," said Alice. "To make sure things are fair let's agree on what counts as an item and make sure everyone's wearing the same number of things. Shoes count as a pair, not individually. Same with socks. No hats. Only clothing counts, not jewellery." Here she shot a look at Deborah, who laughed and said "look, it was worth a try."

Kevin looked around the group. From what he could see Alice was wearing jeans and a shirt, Lucy a figure-hugging dress while Deborah was wearing a skirt with a blouse and cropped jacket on top. He himself was wearing chinos and a shirt, with a vest underneath. Everyone was wearing shoes and he assumed underwear as well.

"I've got six," said Alice. "Seven," said Deborah. "Five," said Lucy. Kevin quickly counted up. "Six, I guess," he said.

"Well, I can drop the jacket," said Deborah, taking it off and throwing it over the back of a spare chair.

Alice looked at Lucy. "You want to take the jacket, or do you have something else to put on?"

"Oh, I don't care," said Lucy. "Let's just play!"

Poker Time!

Alice started shuffling the deck. "She's something of an exhibitionist," she said to Kevin. "I've honestly seen her naked more than I have myself in the last few days."

"Prude," teased Lucy, and grinned at Kevin.

"So," said Alice. "Five card draw, five cards each, one swap, swap as many cards as you like. Losing hand strips. Game on!"

The first thing everyone lost was their shoes. Socks - or in the case of Lucy, tights - came next. Alice lost her shirt revealing a black lacy bra. Kevin lost his shirt leaving him in his vest, which he then immediately lost on the next hand.

Deborah's blouse was reluctantly removed and she kept one arm over her chest largely covering a simple white bra.

Lucy lost next and made a show of peeling off her dress and showing everyone her body. She was wearing a pink lacy bra and a red skimpy thong. Her butt cheeks were beautifully separated by the thin strip of material that only just retained her decency.

"Really?" said Alice. "Red with pink?"

"I wasn't paying attention this morning, just threw on whatever was closest," Lucy said, and turned to Kevin, sticking her chest out. "You like?" she said, giving a little wiggle.

"I- I-" Kevin stammered. "Y-Yes of course!"

"Hah," Lucy said. "I think I've broken him already."

Kevin lost next, and off came his chinos leaving him in just a pair of blue boxers. Lucy eyed him up and down and stared openly at his crotch. Deborah didn't look at all and watched Alice instead, who said "Not looking good for you, is it?" Kevin agreed that it certainly wasn't going his way.

The next hand saw Alice removing her jeans, revealing matching black panties. She didn't seem phased about her state of undress, and everyone was now in their underwear apart from Deborah who still had her skirt - probably much to her relief.

Kevin had a bit of luck with the draw on the next hand and improved his position with a single swap so was quite confident he would do well, but on revealing everyone's hands it seemed everyone else was also blessed and his seemingly-strong hand turned out to be the worst of the lot.

"Well," he said, with a wry smile. "I guess that's it for me. Here goes nothing!" He stood up, peeled down his boxers, quickly covered his manhood with one hand and sat back down.

"Aww," said Lucy. "You could give us a bit more of a look!"

Alice stifled a laugh and Kevin blushed. "What happens now?" he asked.

"Well, we keep on playing," said Alice. "Just try not to lose any more, okay?"

In Extra Time

On the next hand Kevin lost again. "Sorry," said Kevin. "I have nothing left to lose."

"A punishment!" said Lucy. "What could we make him do?"

Everyone fell quiet as they considered the suggestion. Kevin worried about what form the forfeit would take, Alice looked thoughtful, and Deborah - who knows what she was thinking. Lucy jumped up, seemingly oblivious to the fact that she was just wearing bra and knickers. "I have just the thing!" she said, and rushed into one of the bedrooms.

She came back fiddling with some kind of jewellery, trying to untangle it in some way.

"Nipple clamps!" she shouted, apparently very pleased with her suggestion. "Uh-" said Kevin, and looked at Alice, who had something of a sly expression. "Yes," she said. "Good plan."

"I don't think I-" Kevin began, but he was shushed by Lucy. "Don't worry," she said. "They're adjustable, I can make them so they won't be painful or anything." After a bit of fiddling, "There!" she said, holding out her hand.

Draped across her hand was a metal chain, at the ends of which were something like clothes pins but made of metal and much smaller, with rubber covers around the jaws. "Well?" she asked.

Kevin took them in one hand and looked around the room. Alice nodded at him, and Deborah just shrugged slightly. "Right," he said.

Tucking himself between his crossed legs for a moment he worked out how the clamps worked, then gently tested one end on a nipple. It bit at first, slightly taking his breath away, but after a moment began a dull throbbing instead, which was much more bearable. He untwisted the chain and carefully attached the other end to his other nipple. "Okay?" he asked.

"That looked too easy, I think they could have been tighter," said Lucy. "Oh well."

"Right," said Alice. "Next hand!"

Kevin tried not to move too much, as the swinging of the chain was sending little jolts of pain through his nipples. He released his manhood, and with one hand busy covering himself used the other to manage his cards.

He lost again.

"Tsk," said Alice. "That was careless."

Deborah muttered something softly.

"What was that?" asked Alice.

"I said 'handcuffs'," repeated Deborah.

Lucy grinned, and left the room again, returning with some fur-covered metal handcuffs and demanded a wrist. Kevin presented his free arm and Lucy looped the cuff over, ratcheting it closed but not too tight. She tugged the empty cuff sharply over to his hand at his crotch and locked it around that wrist as well. Kevin sat still with both hands over his crotch, the furry material tickling his legs.

Alice dealt the next hand.

Kevin suddenly realized the problem. His cards were on the table but his hands were locked together so he couldn't reach them without taking a hand off his crotch. "Could someone pass me my cards?" he asked weakly, but the girls seemed to ignore him. Instead, he quickly shot his cuffed hands out, grabbed his cards and returned to covering his crotch. His hand wasn't great and he had to swap some, twice more leaving himself exposed while he discarded three cards and collected three more.

And he lost again.

"I think you're doing it on purpose," said Alice. Deborah was grinning now, and Lucy was visibly excited, trying to work out what punishment to apply next.

"And easy one," she said. "Let's just tighten up those clamps."

Not waiting for any acknowledgement she leaned over and fiddled with a thumb-screw on the clamp on his left nipple, each quarter turn sending a jolt of pain through him. She repeated the procedure on his right nipple, and Kevin sat very still, trying not to move a muscle as everything he did would cause another jolt to course through him.

Alice dealt more cards and Kevin was forced to reach for them very slowly this time, giving ample time for everyone to see his penis, which, far from being aroused by all this attention, was shriveling away as best it could.

Of course Kevin lost the hand.

It vaguely passed through his brain that this streak of bad luck was really quite unlikely. Whenever he had a good hand, others' were better. Whenever his hand was bad, nobody else's was worse. At the start of the game losses were quite even, but now he was constantly losing. Somehow Lucy the exhibitionist got to strip to her undies while somewhat-shy Deborah got to keep her skirt. But this thought flittered away before he could properly grasp it and really question what was going on.

He sat quietly and waited to see what judgement came down on him this time.

"I have an idea," said Alice, and headed to the other bedroom. She came back with what Kevin immediately recognized as a small metal butt plug. "You can't be suggesting-" started Kevin, but Alice placed a finger on his lips. "Shh," she said, and Kevin stopped. "Stand up," she instructed.

Kevin stood with his hands in front, covering himself as best he could, smarting slightly from the stinging in his nipples. Alice stood right in front of him, her covered breasts briefly touching the clamps on his nipples. "Now, open wide," she instructed.

Kevin opened his mouth, and she gently introduced the plug. "You'll want to get that nice and wet," she said, holding the plug in place. After a brief pause Kevin closed his mouth around it and started running his mouth and tongue over it, covering it in as much saliva as he could manage.

"That'll do," she said, so he stopped then slowly opened his mouth.

She carefully removed the plug from his mouth, and he closed his jaw. Reaching both hands around him, Alice leaned even closer. She put her head over his shoulder and he breathed in, smelling the sweat on her body. With one hand she teased apart his cheeks. There was a gentle pressure at his anus as the plug was firmly pressed against it. "Relax," she said.

Kevin could make no response to that and couldn't concentrate enough to work out how to comply. But the pressure increased, and with a pop the plug slipped inside. He felt a sharp pain, then a presence in his ass he was entirely unused to. His body immediately tried to reject the intruder but Alice held it firmly in place. "Stop struggling," she said, and pushed it even more firmly in. After a few deep breaths Kevin's ass stopped fighting so much, he was left with a general throbbing sensation, and she relaxed slightly. After she was sure he wasn't going to try to push it out, she took her hands away completely and stepped back. "You can sit down now," she said.

Kevin sat down carefully, exploring the feeling of of the plug in his ass as he did so.

Lucy and Deborah had sat quietly through this. The silence was broken by Lucy simply saying "Awesome."

"Well," said Alice. "Next hand I think," and dealt the cards.

Kevin had considerable trouble concentrating on the cards in his hand and the right play to make, but he'd realized by now that it didn't really matter. Somehow Alice was stacking the deals against him and he was just a play-thing to them. Lucy and Deborah must know as well, and he guessed this was a game they'd likely played with another lonely soul before.

With an air of resignation he discarded his entire hand, and didn't even bother to look at the replacements.

Alice didn't turn them over either. "You lose again," she said. "Lucy?"

Lucy leapt up and ran back to her room.

"You'll want to spread your knees for this one," said Alice. And Kevin dutifully eased himself to the edge of the sofa and angled his legs apart one by one. Deborah sat next to him, making no disguise of staring his body up and down.

"You've clearly been worried about us seeing your dick, so we thought we'd make things easier for you," Lucy said as she returned. "Hands up, please."

Kevin raised his hands off his lap and waited to see what would happen.

In her hands Lucy had something metal which she was separating into two parts. "This chastity cage should help," she said. She knelt down in front of him and gently looped something around his penis and testicles, then levered it closed and clipped it together at the top. She took his penis and gently inserted it into a kind of metal tube, then slowly and firmly pressed this towards the ring. His member was beginning to swell from her touch, but her pressure continued and it soon gave up. The cage connected with the ring and she quickly slipped a small brass lock into one side, locking it and taking out the key.

"There," she said. "All covered up. You're welcome."

Kevin looked down. Where was once his dick was now a sheet metal tube with a rounded end. His testicles squeezed out either side, but all sight of his penis was now gone. He felt a new pulsing as blood attempted to push into his member but found itself nowhere to go.

Alice silently dealt more cards.

Kevin didn't even pick up his cards this time, made no attempt to play. The girls noticed, and quietly placed their hands down as well.

"I think it's time," said Alice.

The Final Act

Lucy and Deborah went to Kevin's sides, and encouraged him to stand. They each took an elbow, and guided him over to the bathroom where Alice had already gone. Kevin's hands were cuffed in front of him, and he offered no resistance.

There on the floor of the bathroom was a large black dildo, suction-cupped to the tile. Alice was pouring some lubricant from a bottle and coating the head and shaft.

Lucy and Deborah turned Kevin so he was facing away from it, then slowly stepped him backwards a few short steps. He felt a hand on his back as Alice steadied him then gently tugged on the butt plug, popping it out from his ass. He heard it placed into the sink.

With Alice's hands on his hips, the other girls slowly lowered him down, knees bending and muscles screaming until he felt the tip of the dildo reach his bottom. He was held carefully in place as Alice guided it in, and the girls lowered him slowly down, all the way to the floor. He squatted there, impaled on the large black dildo, his cock aching inside its cage and his nipples screaming from the pain running through them. His body fought strongly against the intrusion in his butt and his anus spasmed around it as it tried to push back. Alice stood behind him, hands on his shoulders preventing him from rising. All his weight was on his ankles, but as his body adjusted he leaned onto the dildo slightly as well, using it to take some strain off his legs.

"Beautiful," said Lucy, who had already removed her bra. She looped her thumbs through the waistband of her thong, and tugged it down. Stepping out she tossed it back into the room behind her and stood right in front of him. Kevin stared at her naked, beautifully-toned body. Her crotch was waxed completely smooth.

She stepped forward, placing her legs either side of his and placed her hands on his head. She pushed her crotch right up to his face and he instinctively knew what he was expected to do.

He tilted his face to better align with her body, then lashed out with his tongue. He licked greedily up and down her slit, and teased his tongue around her clit, occasionally giving it a direct tap.

He settled into a rhythm of lapping up directly over her clit then running down beside it, up again, then down the other side. He kept going, as she trembled slightly, thrusting slightly into him as he worked. After some minutes Lucy held his head even more tightly, and pressed herself into him even more. "Keep going, keep going, don't stop..." she said, and Kevin continued doing exactly what he was doing: up, down-left, up, down-right, up...

Lucy gasped out a profanity and squeezed into his face, so tightly that his tongue could no longer continue and he was left licking at whatever he could reach. She pulled away, panting heavily, and staggered into the lounge and sank to the floor.

Deborah reached up the back of her skirt and pulled her panties down, stepping one leg out leaving them dangling around one ankle. She stepped forward and raised her skirt just enough to loop the hem onto his head, then paused and quietly muttered "Please?"

Kevin eagerly went to work, burying his face into her pubic hair and exploring her pussy with his tongue. She tipped his head further back and tilted her hips further upwards, letting him push his tongue slightly into her vagina, which he repeatedly did, in and out, over and over again. She eased herself backwards a bit and he could no longer reach into her, so focused attention on her slit instead. He lapped up and down and she reciprocated, grinding into him as he did. He moved to her clit and ran his tongue over it at which she leapt back slightly, so he tried again much more gently, just touching the surface with his tongue and pressing it forwards and back so very slightly. She responded well to this and after a minute suddenly pulled away from him, bending at the hips and clenching her legs together as a climax shuddered through her. She leaned forward, putting her weight on his head and pushing him firmly down onto the big black dildo still impaling him. He made no complaint but bore it out, and she shook slightly as the orgasm subsided.

Presently she let go of his head, easing his aching rectum slightly, stepped back and slipping her leg through pulled her panties up again. "Thank you," she said, and walked back into the lounge.

With Deborah satisfied, Alice now let go of Kevin's shoulders but he did not try to rise. She walked around in front and fiddled with her bra. "You know, you could have stopped the game and gone home at any point," she said, as she worked the clasp then pulled her bra off.

"I know," said Kevin. "But by the time I worked that out I was wondering where all this would lead."

"Good boy," she said. "And are you happy with this ending?" She started working on her undies.

"Very much so, yes. Although the nipple clamps are definitely giving me quite a bit of trouble."

"Brace yourself," said Lucy, who had just reentered the room. She leaned in and took hold of each clip. She squeezed them both at the same time, and Kevin yelped as blood rushed in causing a stab of pain worse than he'd felt before. "Easy," she said, as she gently rubbed his nipples to soothe them.

Alice stepped forward and presented her pussy to his mouth, which he eagerly started to work on.

"You've done very well, and if you're up for it we can play again tomorrow. We'll do something a little different this time, something much more fun for you. I think we'll leave you in the cage for now though, to ensure you do come back. After all, there are no hardware stores around here, and it would be tricky getting through airport security with that attached to you. But if you're good, it'll come off tomorrow and your dick can come out to play."

Kevin murmured his agreement as he plunged his tongue deep into Alice's pussy.

This was definitely looking like a holiday to remember.