The poker bet - The misadventures of Mitch Jacobson

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The poker bet

The misadventures of Mitch, a spin off from the best friends stories. It is a standalone story but there may be more misadventures to come.



Mitch had been forced to take some time off work, he hated not working, working was the only thing he was really any good at. Vacation was now mandatory in Mitch’s company apparently, his business partner was passionate about work/life balance and Mitch agreed to all kinds of rules he didn’t follow himself and never would have agreed to if he thought they applied to him. For some reason his business partner was being a dick about this rule. As one of the company directors he had to set the example, that’s what his he said anyway. So he decided to spend some time at his beach house. He inherited it a few years back and hadn’t been there since he was a kid. It was about time he paid a visit, if only to make sure that the cleaners and groundsmen were actually doing what he was paying them to do.

Upon arrival he was pleasantly surprised to see the old place looking just as he remembered, the grounds were well maintained and the cleaners had gone to extra trouble knowing he was visiting, filling vases with flowers and stocking the fridge with essentials. None of that mattered to Mitch but he appreciated the efforts. He dumped his bag in the hallway and went up to check out the rest of the house. It was just as he remembered, now what the hell was he going to do for the next few weeks. He set up his laptop and connected to the Wi-Fi to check his emails. Nothing. His PA was was eager to prove to him that they could manage without him and there was no way they would bother him on day one. He headed down to the cellar to see what wine of any still remained.

The beach house belonged to his great aunt, she loved good wine and at one point the cellar was very well stocked. Fortunately the cleaners had been keeping the cellar clean, the bottles were dusty but the pathways had been regularly swept and the cobwebs kept at bay. He browsed the old bottles to find one that he might like. A 1985 Henri Jayer Cros Parantoux, that will do. He grabbed the bottle and headed to the kitchen to find a suitable glass. Then took the bottle and the glass to the garden. The garden overlooked the beach, a small pool surrounded by some comfy chairs.

The wine was great, he wasn’t sure it was worth the price tag but he didn’t pay for it and he was now pleasantly tipsy. As the sun began to set he decided to take a stroll along the beach, he figured that’s what people do right. He did his best to admire the view as the sky turned a deep hazey orange colour. He strolled along the beach as the waves kissed his feet and he finished the bottle of overpriced wine.

This was a mistake. What was the point in coming all this way to relax when you have a perfectly good apartment, you have clubs and restaurants who know you. This sleepy old beach town can’t compare to the city. When he was a kid he used to find the beach exciting, it was just dull to him now. In the distance he could see a bar, he quickly checked that he was carrying his wallet and headed towards it, if he had to be on vacation, he should at least be drunk.

The bar was small and surprisingly crowded. Full of locals, apparently there’s not much to do around here. Mitch went straight to the bar and ordered a double shot of whiskey on ice, the most expensive one they stocked. He looked around for a spare seat. The nearest empty seat was near the poker table. Mitch was not much of a poker player, he played now and then but normally lost. Poker is an expensive game to play when you aren’t very good at it but Mitch had money to burn. He took a seat near the poker table, having no intention of playing. When Mitch played poker it was because he was interested in the other people playing, winning or losing was never important. He was very interested in the players. Considering this was not a casino the stakes were pretty high, it was a friendly game in a local bar in a sleepy beach town but the players were not messing around, it appeared to be a 5k buy in. Mitch was soon engrossed in the action. Before long Mitch had was drunk on cheap whiskey and making friends with the locals as they all observed the tense table.

Poker was a nightly event here, but 5k nights only happened once a week. Mostly it would be David and Sam. Both were good looking guys in their mid 20’s, good at poker and normally played with their winnings. Recently though David had been had been on a losing streak. He had lost the last three 5k nights in a row and many games during the week.

David was a skinny guy but well toned, probably a surfer type, wavy strawberry blond hair, some tribal tattoos on his calfs and biceps. David was playing well and seemed to have all the luck tonight. He needed it. Unfortunately his luck didn’t last the night. Sam managed to turn it around just before it was too late and walked away with everything. David was desperate, begging him for another game but Sam knew David couldn’t afford another 5k buy in and he definitely couldn’t afford to lose again. Sam wanted to celebrate with a few drinks but he left the bar with his winnings to avoid the inevitable conflict with David. He and David were good friends and he had actually hoped David would win this week, he enjoyed their weekly high stakes games, it wasn’t about the money for him, he enjoyed the competition. He knew that David was at his limit, this would probably be the last one. He didn’t want to take any more of David’s money anyway.

Mitch felt for David. He brought him a drink and tried to comfort him. David was beyond comforting though. He really couldn’t afford to lose, he took out a loan to play that game, he was already in his overdraft. Basically he was fucked.

Mitch: look, I’m here alone and could do with some company, I’m notoriously bad at poker so why don’t we play a little. You might have better luck against me.

David: I have nothing to bet

Mitch: do you have a car?

David: I do but it’s not worth much, maybe 500 at best.

Mitch: okay, I’ll play for your car, let’s say it’s worth 1k.

It didn’t take long for David to win Mitch’s 1k, he was still fucked but it helped a bit. He decided to try his luck and ask Mitch for another game, that was always Mitch’s plan. Give the poor guy a chance to win back everything he lost tonight. David won the next game. They played another for 2k each before it was time for the bar to close.

Mitch invited david back to his house for one more game, he could put the whole 4k in and hopefully win 8k. By now they were both drunk as hell and the best of friends. David was no longer worrying about his debt, he was too drunk for that and Mitch really was terrible at poker. They went back to Mitch’s beach house. David took a seat by the pool while Mitch searched around for poker chips and a good bottle of scotch. It took a while to find the chips and when he joined David he was in the pool.

David: you don’t mind do you? It’s so hot tonight.

Mitch: not at all, I might join you.

Mitch passed David a whiskey and joined him in the pool. David had stripped to his underwear, a pair of white Calvin’s, the kind that are see through when wet. Mitch dipped his head under water and got a good look but refrained from perving out too much, he was supposed to be helping David. David was well toned with well defined abs, a perfectly peachy ass and although his dick was mostly covered by the double layer of fabric on the crotch part of his boxers, it was hanging down to the left and Mitch could tell his was well hung.

There was no need for Mitch to worry about getting caught looking at David. He was too drunk to notice Mitch’s shorts tenting under the water, and way too drunk to notice he was being ogled. After a few more drinks and some mild horseplay Mitch was starting to get a little too horny. He got out of the pool to cool off from cooling off, it was making him way too hot. He wrapped himself in a towel to hide his boner. David didn’t notice his boner, he didn’t look at guys dicks. Mitch took a seat by the pool and set up the poker chips.

Mitch: are we going to play another game of poker then? Or did you come here just to swim?

David: oh shit, I’m a bit drunk, I forgot all about the poker.

As David pulled himself out of the pool his underwear slipped down his hips a little, exposing his pubes and the base of his shaft. He walked over to the towels Mitch had brought out without adjusting his boxers and bent over to reach for one. His boxers were clinging to his ass and the pattern of his ass hairs was clearly visible. Mitch watched out of the corner of his eye as he set up for the poker game. David didn’t wrap himself in the towel, he just dried his hair and face a bit and chucked it on his seat as he sat down. David poured them both another glass of whiskey as Mitch shuffled and dealt the cards.

Mitch was just about as good at playing to lose as he was at playing to win. David started off playing well and Mitch was soon down and figured his good deed was nearly done. The sight of David’s glistening abs in the moonlight was almost too much for him. David poured the last of the whiskey, he currently had 6k chips and was confident he would win, his troubles were over. He lost the next hand, nothing to worry about, Mitch was awful at poker, he still had this. He lost the next, they were even now.

Try as he might Mitch couldn’t seem to lose, he was betting big on every bad hand and folding the good ones but somehow David’s luck was so bad he couldn’t even win when the odds were stacked in his favour. As the chips started to to stack up on Mitch’s side of the table he began to stress out, this wasn’t meant to happen.

He went inside to find more whiskey. He filled both of their glasses and dealt another hand. Surely nobody could be this unlucky. David was almost out of chips, he had a good hand and went all in. Mitch hadn’t even looked as his cards yet, he matched David’s bet. David wanted to bet more but he had no more chips and Mitch wanted to bet more so David could win it all.

David: can I bet you my car?

Mitch: I really don’t want your car dude.

David: you offered 1k for it earlier.

Mitch: you said it was only worth 500, I was being nice.

David: come on. Please.

Mitch took the opportunity to once again show charity to David. He accepted the offer for his car and went all in, still not having seen his hand. It was all or nothing for David. If he wins he walks away with 8k but if he loses he has nothing, not even his banged up old car. They both turned over their cards. Mitch won. They were both in shock. As reality set in David went pale, he almost started to cry.

David: dude you have to give me another chance, I can’t afford to lose my car. I need it for work, if I don’t have my car then I can’t work and I can’t pay my loan. Please.

Mitch: okay, don’t worry, we can figure something out.

He dealt another hand.

David’s luck was in, he had a good hand and was again feeling confident that he could win, but he had nothing to bet.

David: what do I bet you?

Mitch: I don’t know, what have you got?

David: ugh. Nothing, I’m on my ass.

Mitch: so bet your ass then.

David: huh? What does that even mean?

Mitch: I don’t know, you tell me. I’m drunk dude, just bet something so we can finish this damn game already.

David: hahaha, ok so I bet my ass.

Mitch slyly took out his phone and hit record.

Mitch: ok so to be clear, you’re betting your ass, what does that mean to you?

David: if you win my ass is yours. I guess you can do whatever you want with it.

Mitch still assumed he would lose this hand, he had never been this lucky playing poker and he wasn’t even trying. His dick was starting to get hard at the mere mention of David’s ass. Each time David said ass he saw visions of David bending over to reach for the towel, the peachy globes spreading apart and revealing a perfectly hairy hole.

Mitch: I’m not sure what I am supposed to do with an ass but I guess we don’t have much choice.

David was all in, all he had was his ass and he just bet it, Mitch went all in too. They revealed their cards.

David: FuckShitCunt….Motherfucking.. what the absolute fuck.

Mitch: I’m sorry dude

He poured another whiskey for David. David downed it as he held in tears of frustration.

Mitch: okay, so, I guess now own your ass..

David: what?

Mitch: you bet your ass, now your ass is mine.

David: you’re joking right?

Mitch: if you’d won you would have taken my money right? Well I won so bring me your ass.

David: what are you going to do with it?

Mitch grabbed his phone and hit play on the video. “if you win my ass is yours. I guess you can do whatever you want with it.”

Mitch: whatever I want

David: this is getting weird dude, I’m out of here.

Mitch: you owe me your ass, unless you have another way to pay your debt?

David: you know I don’t.

Mitch: then get your pretty ass over here.

David stood up and walked over to Mitch, he turned away and presented Mitch’s winnings to him. Mitch grabbed and squeezed it.

Mitch: Very nice.

He slapped it.

David: alright dude, enough.

He started to walk away.

Mitch: whoa. I’m just getting started.

Mitch reached out grabbing David’s waistband and pulled him back towards him.

He pulled down David’s boxers and grabbed his ass with both hands.

David: this isn’t funny. Enough already.

Mitch: you owe me your ass and I’m taking it. Now bend over and let me have a proper look at my winnings.

Mitch pushed David’s back forward and stroked his fingers gently over his crack. As his fingers brushed against David’s asshole David stepped forward and pulled up his boxers.

David: alright, you had you fun. We’re even.

Mitch: we’re not even, this ass is worth 8k right? That was the bet? Would you pay 8k to just touch something? Your ass is mine to do whatever I want with it. Now get your ass back over here and pay your debts.

David: I’m not gay dude, this isn’t cool.

Mitch: I don’t give a fuck what you are, you should have thought if that before you placed the bet.
 
David reluctantly returned to his previous position and pulled his boxers down just enough to expose his ass. Mitch slid them down to his ankles and pulled them off him. He threw them into the pool and slapped David’s ass. David gritted his teeth.

Mitch stroked, groped and prodded and occasionally slapped David’s ass. As he did so he noticed David’s balls begin to tighten and his shaft thicken. He lubed a finger with spit and gently placed it against David’s hole. David’s dick jolted forward as Mitch’s finger made contact with his hole. Mitch applied a gentle pressure and wiggled his finger around until it started to enter David’s hole. As the tip of his finger entered his ass David let out a hushed whimper. Mitch looked between David’s legs to see his dick fully hard. With an inch of his finger inside David’s ass he took his free hand and grabbed David’s dick.

David pulled away.

David: don’t touch my dick, you only won my ass, the dick is still mine.

Mitch: okay, you’re right. How about we make a deal?

David: what do you mean?

Mitch: your ass is mine, I can do whatever I want with it. I’m going to fuck you tonight. You have some options. I fuck you and you leave with nothing, I still own you ass and can claim it whenever I want, meaning I can fuck you whenever I want. The only way you can get it back is by winning it back. You will need to bet me at least 8k. Or….. we come to another arrangement.

David: you know I don’t have 8k, I never said anything about fucking, and who said anything about whenever you want it. You’re taking this too far, you can’t just fuck me whenever you want forever.

Mitch: I also won your car, is there a time limit on that? Can I only drive it tonight or is it still mine tomorrow?

David: uhhhh, but you can’t fuck me, that’s not just my ass, that’s my insides.

Mitch: the only thing stopping me from fucking you is your ass, I own the entrance so I get to use it.

David: so what’s the deal.

Mitch: you let me fuck you tonight. I get your whole body to do what I want with and you can have your ass back.

David: fuck no.

Mitch: I’m going to fuck you either way, this way it’s just a one time thing.

David: What about my car?

Mitch: what about it?

David: I want my car back too.

Mitch: fine.

David: and the money!

Mitch: deal. Now get over here before I change my mind.

David stepped back over to Mitch. As soon as he was in reaching distance Mitch grabbed his still hard dick and pulled him closer. With his other hand he grabbed his neck and pulled him in for a kiss.

David pulled away, “no kissing”

Mitch: you do what I want tonight, stop fighting me or the deal is off.

Mitch tightened his grip around David’s neck, David could barely speak, he nodded and leaned in for a kiss. He realised he had no choice, he had agreed to this and Mitch was right, he couldn’t fight him or he would lose everything. As David relaxed into the kiss and Mitch could tell that he was no longer fighting he released his grip on his neck and started touching his body while still keeping a firm grip on his dick. His hand slid down his body, stroking his pecks and his nipples, his abs, his hips. Mitch pulled away from the kiss.

He stood up, still holding David’s dick and used it to lead him to the bedroom. As they walked towards the house David looked back at his boxers floating in the pool. Then looked down at his rock hard dick. Why the fuck am I so fucking turned on right now.

When they got to the bedroom Mitch told David to lay down while he stripped naked. David anxiously did as he was told. Mitch climbed onto the bed and grabbed David’s face, kissing him aggressively before licking every port of his tight muscular body. Even though Mitch was no longer touching his dick his boner wouldn’t let up. It twitched and bobbed about as Mitch caressed his body with his hands and tongue. Eventually Mitch made his way down to David’s dick. He swallowed the full length of it in one swift move and proceeded to give David an expert blow job. David writhed in ecstasy as Mitch did things to his dick no girl had ever done before while his hands continued to grope and squeeze his torso.

David was too drunk to fight the feelings of pleasure, he left his inhibitions floating in the pool with his Calvin’s, he closed his eyes and relaxed his body as Mitch continued to suck him off. Before long David was struggling to control himself, he was moaning and crying and his dick was desperate to release a load, he had no willpower left to stop himself. He shot a huge load in Mitch’s throat that Mitch happily swallowed. Mitch sucked his softening dick clean as he pulled away from it and then kissed David on the lips with cum still dripping from his mouth. As Mitch slipped his tongue into David’s mouth the taste of his own cum mingled with David’s spit. Mitch then spat some of David’s load into his mouth and grabbed his jaw to stop him drop spitting it out.

Mitch: swallow it.

David struggled a bit but Mitch was stronger than him and he was in no state to fight. He begrudgingly swallowed his own cum.

Mitch: good boy. Now it’s your turn.

Mitch positioned himself over David and pushed his dick into his mouth. David didn’t fight it but he had no idea how to suck a dick, he just opened his mouth and allowed Mitch to fuck it. As Mitch fucked David’s mouth he pulled David’s legs up and explored his ass some more. He spat on in and pushed the spit in with a finger, this time he managed to get more than in inch in, he pushed and wiggled until the whole finger was inside and then moved it around. After a while he slipped in another finger.

David’s sloppy blowjob wasn’t doing much for Mitch and David was gagging and crying constantly. His face was covered in tears, spit and puke from each time Mitch’s dick had entered his throat. Mitch got up and threw a towel on David’s face.

Mitch: clean yourself up, you’re fucking disgusting. Make sure none of that shit gets on my sheets.
David’s legs were still raised as he cleaned his face, Mitch lifted his legs a little more and licked his asshole. He slipped his tongue deep into his ass and licked all around the inside. David moaned a little as his dick twitched with anticipation. Mitch pulled out his tongue and spat on David’s ass. Just as the spit started to roll off his hole and onto his ass crack Mitch blocked its path with the head of his dick. He pushed the spit back up to David’s hole and applied just enough pressure for his tip to enter. David was starting to get hard again.

Mitch grabbed David’s semi hard dick with one had as he pushed his own rock hard dick into David’s ass with the other. David’s ass was tight. It had stretched to make room for Mitch’s dick but was desperately trying to to get back to its original size. Mitch kept pushing his dick in using his hand to shove more in and used his body weight as he leaned down on top of him. David moaned more with every inch of cock he received. His dick was now fully hard again and oozing pre cum all over his navel. As the last few inches of his dick entered David’s tight ass Mitch started to rock his hips back and forth while he stroked David’s oozing cock.

Every muscle on David’s rippled torso tensed as he felt the pleasure and pain of penetration. He didn’t expect it to feel like this. Mitch continued to pound his ass while jerking his dick as David moaned and cried but never once asked him to stop. Soon David’s balls began to tighten and his legs started to shake. Mitch fucked him harder and tightened his grip on his dick. He jerked him more aggressively as David tried his hardest not to cum. David couldn’t hold back the torrent of cum he was about to release. It came out with a force hitting him in the face, Mitch continued to fuck and jerk him off as stream after stream coated David’s body. When he finally released his grip on David’s dick, it continued to ooze cum for a few minutes. David groaned as his balls attempted to push out cum that didn’t exist. Mitch started scooping up handfuls of David’s cum, pushing it into his mouth and demanding he swallow it. At this point david was no longer able to fight. He was weak and exhausted. Mitch continued to feed him cum until it was all gone, then came in his ass. He got into bed, while pushing David onto the floor

Mitch: okay, you can fuck off now.

He rolled over and closed his eyes.

David climbed to his feet, his legs were weak and his ass was sore, he stumbled down the stairs. He retrieved his clothes, the bottle of whiskey and the 8k from the garden, and vanished onto the darkness of the beach.

All that remained as a reminder of the nights events was an empty glass and his Calvin’s still floating in the pool.
 
The Poker Bet - The Misadventures of Mitch Jacobson encapsulates the thrilling escapades of Mitch, a daring gambler whose life revolves around high-stake poker games. With each hand dealt, Mitch finds himself entangled in a web of suspense and excitement, showcasing the unpredictable nature of the game. Through witty dialogue and nail-biting scenarios, this story promises to keep readers on the edge of their seats till the very last card is played.
 
The Poker Bet - The Misadventures of Mitch Jacobson encapsulates the thrilling escapades of Mitch, a daring gambler whose life revolves around high-stake poker games. With each hand dealt, Mitch finds himself entangled in a web of suspense and excitement, showcasing the unpredictable nature of the game. Through witty dialogue and nail-biting scenarios, this story promises to keep readers on the edge of their seats till the very last card is played.
I appreciate the write up but it is unfortunately a fiction just as the original story is. When i share a story i expect the audience to come to their own conclusions about the characters and their motives and emotions but no part of what you wrote matches the story i shared.

Mitch Jacobson is a tragic character who receives little sympathy due to his extraordinary wealth. His life of great opulence that would be the envy of most people does little to make up for emptiness he feels inside. He has a deep seated fear of rejection that causes him to seek out intimacy without the risk of rejections.
This is a story of one such instance, one that despite all odds could have bloomed into at least friendship had Mitch not instinctively rejected David. It is a possibility that David enjoyed the experience and would have stayed with Mitch, that the most painful part of the evening for him was being rejected by Mitch. We will never know but more importantly neither will Mitch, that's his way.

The story you wrote about sounds fun, you should use your obvious writing skills to make that story real. I would love to read it.
 
I especially liked the way the story unfolds with unexpected twists, not letting you go until the very end. It's like watching a comedy of errors unfold right in front of your eyes. It makes you think about the crazy bets that people make and what it all leads to. It's all fun and games until someone puts their favorite pair of socks on the line or something equally absurd, right?