** I don't Hannah Montana or any of it's characters. **
*Not exactly sure of the rules for strip poker so forgive me if there are some error*
Jackson, Jake, and Oliver sat around the poker table Jackson had found in his basement. The girls and Robbie Ray were at a Hannah Montana show and wouldn't be coming home until the next day. The guys figured it would be okay to gamble since Robbie Ray wouldn't normally allow it. Dealing went around the table. Poker chips, which were supposed to be going from one play to another, all seemed to be going to Jake.
"Jake, how do you do that?" Jackson cried.
"When you're good, you're good," Jake smiled triumphantly.
"Well, no offense but losing to you," Oliver interjected after an hour and a half, "Is becoming somewhat tedious. I'm almost out. Only we change the game, I'm pretty much done."
"Why Mr. Oken, are you suggesting we raise the stakes of the game?" Jake asked, one eyebrow raised.
"Okay but to what? We've already lost almost all of our money to you. What else do you want?" Jackson asked.
Jake looked at them with an idea. "We could always play strip poker."
Jackson and Oliver recoiled in disbelief. "Strip poker?" they said in unison. "But they're aren't even any girls here," Oliver remarked.
"What's the matter Oken? Afraid you're gonna lose?" Jake asked.
"No, let's play. I feel like my luck's about to turn around," said Jackson.
"Then play on," said Jake, passing him the dealer chip. Oliver looked at Jackson questioningly before throwing his cards back into the pile.
"And by the way, shoes and socks don't count," Jake smugged.
Jackson shuffled the cards and then dealt them. He looked at his cards. He had the potential for two pairs, three of a kind or four of a kind. He put his cards down. He placed the top card down to burn it and remarked, "Well gentleman, how many cards would you like?"
Jake looked at his cards. He had three different cards with no single combination. Without looking at Oliver, he put down two cards. Jackson dealt him two new cards. He now had a pair. He was gonna have to bluff his way through this hand, hoping the other two would fold.
Oliver looked at his cards. He had three of a kind. "None," he replied.
"Ok, here we go," Jackson added before putting three cards down. Another card of Oliver's came up, giving him four of a kind, and another card of Jackson's, three of a kind. "Time to show your cards," Jackson added.
"I'm not sure of the rules of strip poker, but do we have to bet stuff?" Oliver asked.
Jake saw his opportunity. "Yup you do. Oliver, since you're to the left of the dealer, you go first. What are you willing to bet?" Jackson nodded.
Oliver looked stumped. "Your shirts I guess?"
Jake looked content. "Okay, I either fold or match his bet- in this case my shirt. You guys get the idea?" When they both nodded, he continued, "So, I bet my shirt and…. I wanna raise. The person with the lowest hand has to kiss the other person. Sound fair?" Both of them were in shock but neither one of them wanted to fold so they nodded, automatically condemning themselves to that fate.
"Hey, if you wanna fold, that's fine by me."
"No," said Jackson shyly.
"So what do you say Jackson?"
"I'll see your bet. No raise," he sighed, picking up his cards and looking at them again.
"Anybody wanna fold?" Jake asked. Oliver and Jackson looked at each other but said nothing. "Ok. Jackson, what do you have?"
"Three of a kind," Jackson, winced, hoping it was enough to beat them.
"Four of a kind."
"This sucks…" he sighed inside, "I only have a pair."
Oliver perked up. "Wait a second, this means I won! I'm not losing any clothes!"
Jake looked up at Jackson. "You know, maybe strip poker wasn't such a good idea," he began saying.
Oliver butted in. "No way. You're the one who suggested it so now you have to go through with it."
Jake resigned and stood up. He removed his muscular t-shirt, threw his light blonde hair to the side and walked over to Jackson on the other side of the table. He had just removed his loose t-shirt and was squinting. Jake sighed on the outside and moved to Jackson's face. He was basically the same height as Jackson so he didn't have to crouch. He stood there, working up the nerve as Jackson stood there anxiously.
"I'm waiting guys," Oliver said jokingly. He didn't think they were going to go through with it.
Jake moved the few inches forward and his lips met Jackson's. "This is disgusting," Jake thought to himself until he realized he actually enjoyed it. Just to make it look convincing to Oliver (Jake thought) he put his hands around Jackson's face.
Jackson's eyes went wide when Jake's lips met his. However, Jake's lips were smooth, not unlike what he'd expect them to be. Suddenly, he felt Jake's hands at the back of his head. He didn't care though. This kiss was breathtaking.
Oliver laughed. Jake had been so cocky, waiting for the two of them to fold. Now he was the one who had to kiss Jackson. Although it wasn't a bad sight to be honest. "Woh," Oliver thought to himself. "Did I really just think that?" If his hardening penis was any indication then yes he did. "All right all ready. Joke's over. C'mon. Another round," Oliver beckoned them back to the table.
Jake let go Jackson's head. Jackson's head was still reeling from the kiss and so was Jake's. "Play it cool, play it cool," Jake thought. Jackson didn't care.
Next hand got dealt out. They all had good poker faces so none of them knew of the others had a good hand or not. "Okay guys. Time to bet," Jake said. Oliver and Jackson looked at each other, trying to decide if he was actually being cocky or if it was all show.
"Jake, I believe you bet first," Oliver noted.
"Right. Your pants," he said. He didn't want to go any further but he knew he had a good hand and decided to risk it. "Your pants and you have to switch underwear with the other loser."
Jackson and Oliver both looked on in shock. They couldn't believe the bet but they weren't going to fold now. However, neither of them wanted to lose because they both had slight hard-ons. "Anyone care to raise?" Jake asked. Both shook their heads furiously. "Okay then my fine men, it's time to show your hands."
Jackson laid down a flush. Both Oliver and Jake were in shock. Oliver threw down his two-pairs while Jake laid down his straight in shame. Jackson laid back in his chair with pride, arms folded across his chest. Just as Oliver went to undo his belt, Jake bolted to the poker table. "Wait! I have an idea—another bet. High card draw. If I win, no one takes their pants off," Jake began to explain. Oliver nodded excitedly.
"Why would I do that?"
"Because I'm gonna raise the stakes. If I win, no one takes off their pants. If you win, we'll do what we were going to do."
"No. The only way I'll agree to this is if my rewards are higher too."
"What do you mean?" Oliver questioned, sitting back down.
"Like Jake said, if he wins no one takes their pants off but if I win, you both lose your pants, you switch underwear, and Jake, since you're the one playing, you have to… kiss Oliver while groping him, as much as I don't want to see that." In all actuality, Jackson really did want to see that.
"Fine," Jake replied.
"Oliver, I always win this. Trust me," Jake answered, not even looking at him.
"Jake I will let you draw first." Taking a deep breath, Jake sighed and pulled the top card. 10. Good. He showed Oliver and Jackson.
"Your turn," Jake said, turning the deck towards him. Jackson had a smug look of contempt on his face as he picked up a card. He looked at it and then flipped it over. Queen. Jake's head fell back and Jackson put a cocky grin on his face.
"Well, get to it there Zombie Slayer."
"2 of out 3 Jackson. Please," Jake whispered.
"I wouldn't risk all of that," Jackson whispered in his ear before waving him to the other side of the table.
Oliver glared with contempt at Jake. Oliver went back to begin to undo his belt. He pulled it out, not even thinking about what was going to happen next. He held his pants up for as long as he thought Jackson was looking but Jackson wasn't paying any attention to him. He was watching Jake. Jake turned to face him. "I have no shame," Jake said. He secretly had plenty of shame, especially about this. He knew that his shorts were the only thing covering his semi-erection and he did not want the Jackson or Oliver to see it. Oh well. He undid the button and slid the shorts down to his ankles.
"Tightie-whities Jake?" Both Jackson and Oliver said at the same time. They couldn't believe that their celebrity friend wore them.
"Yeah, so? They give me support where I need it most," Jake explained. He was trying hard not to be embarrassed as he could clearly tell that Jackson saw his boner which was growing by the second. He turned to Oliver in his plaid green-white boxers. Did he see a slight bulge?
"All right Jackson. Where can we exchange underwear?" Jake asked.
Oliver sighed. "Look, it's not like it's anything we haven't seen before. We'll just do it fast and nobody will see anything." Jake was getting more embarrassed by the minute, his face now clearly red. After sighing, he stepped out of his underwear and gave it to Oliver who did the same. They both saw the other's dicks.
Jake had a nice one. It looked to be around 3" soft but was a good 6' incher now and was still growing. Oliver meanwhile, Jake noticed in astonishment, had a great dick! Thick but smooth, it looked like it tasted great! Jake did not just think that! It looked like it was 5" now and it didn't look like it was stopping.
Jake stepped in Oliver's boxers and felt his balls swinging about. Oliver stepped into and pulled Jake's tightie-whities' up and grimaced. "Jake how do you fit into these things?" Oliver asked.
Jake just shrugged. "Now, onto the second part of the bet," Jackson reminded them. Jake had forgotten he was still there. Jake walked over to Oliver and remembered a kiss he had learned on Zombie Slayer. It was rough but it was the only one he could think of that coincided with groping someone. Jake looked directly into Oliver's eyes before putting his lips onto his. Without realizing, Oliver felt his hair being pulled back tight while his dick was being caressed. His eyes rolled up into their sockets from pleasure. He had never felt anything so good, even in the tightie-whities. Oliver gripped onto Jake's sides. He began moaning into Jake's mouth but Jake didn't stop the kissing.
Jackson's was getting very turned by this. Naked men, fondling… it was great! And, if Jackson didn't know any better, he was have guessed from the groping Jake was giving Oliver that he starred in gay porn more than in Zombie Slayer. "Ok. You're good," Jackson declared, tossing the dealer chip to Jake. Jake shook his head and hair to realization and went back to his chair. Oliver stood still in the spot for a moment before continuing.
Another hand was dealt. Three more cards were drawn. "Bets please," Oliver called. He was still shaky from the last play but all right.
Jake called, "If I win, you two have to take off the only piece of exterior clothing you have on—shirt and pants."
"Fair deal," Jackson concurred. He had a full house. He wasn't afraid of losing this round at all. "And hell, why not? Since this night has some sort of gay theme to it, the person with the lowest hand has to mouth the other one off."
"Mouth?" asked Oliver.
"Bullshit," Jake called.
"Does that mean you fold pretty-boy?" Jackson taunted.
"Fine. You know what? Let's play," Jake responded.
"Mouth? Guys, what's 'mouth'?" Oliver asked.
"How do I put this tastefully…?" Jake began.
"You don't. It's when you mouth a guy's penis through his boxers… or underwear."
Oliver made a disgusted look but decided to play.
"Anyone wanna raise?" Jackson asked. They glared at him. "Then show me what you got."
Jackson put down his full house. Jake was amazed. He also had a full house. They looked at each other. "So which one of us is going to be the loser?" Jake asked.
"You both are," Oliver answered, putting down his four of a kind. Jake and Jackson looked from his cards to each other again.
"But how do you know who gets…" Jackson couldn't even finish the sentence. Jake shrugged.
Oliver pulled the deck. "High card wins."
Jake pulled out a nine. He was desperately hoping that Jackson would get an eight or seven. Jackson picked up his card and pouted. 3.
Oliver smirked. "Now for this to work Jackson, those shorts have got to go." Jackson frowned as he removed his shorts and revealed his white briefs. It also revealed his massive boner. Jake realized that this would be easier than he thought.
Jackson turned his chair outward towards Jake and Oliver. Jake went down on his knees and with some trepidation went to work. He licked his way up Jackson's dick, moving slowly but gracefully. Jackson let out a small moan. Jake changed his pace, moving quickly and then slowly, back and forth.
Jackson was loving it. Feeling a smooth tongue on his dick, even if it was through his boxer briefs, was amazing. He gripped the sides of the chair to steady himself. Jake was doing a great job, whether he knew it or not. Jackson was panting at this point. He knew what was about to happen. "Jake, fair warning…" Jackson said. Jake pulled up and away, having an idea too. Suddenly, Jackson began cumming in his briefs.
Jackson leaned his head back, eyes closed. Jake looked down at Jackson's briefs, never having seen another guy cum before. Oliver looked at Jake. He had a hard on now so bad it hurt in the tightie-whities. He was desperate to touch himself but he figured he could wait until he got home. "Right?" Oliver thought to himself.
Jake shook himself out of his stupor. "All right guys. Who deals next?" he said, bringing himself back to his chair. All he could think about was that he had never made a guy cum before.
The cards were dealt out. Hesitatingly Oliver said, "Bets."
Jackson said, "I say that whoever wins gets to remove any cum-soaked piece of clothing he has on. "
"But that only affects you," said Jake.
"If you win," chimed in Oliver.
"Well then what do you guys wanna bet?" Jackson asked.
"Ummm…. How about the losing player does something intimate?" Oliver suggested.
"More intimate than what we've done?" asked Jackson.
"Which includes kissing another guy, groping, and… making him cum in his own boxer briefs?" Jake reminded. Jackson looked down, either embarrassed or ashamed.
"Oh. Well, I guess," Oliver said bashfully.
"What else is there besides fucking?" Jackson asked.
"No! No fucking at all! Not today or ever!" Oliver announced.
Jake laughed. "Funny." Oliver thought about what to do while Jake and Jackson looked at each other, knowing what the next move was. They had both had it done to them but they figured that no one had done it to Oliver. "Umm, Oliver I think the next step is to suck someone else's dick."
"What?! No it's not. It's…" Oliver's eyes went wide as he realized this was true. "Oh god," he whimpered as the cards were dealt out.
"So losing hand takes care of the other player is the final bet?" Jake implied. Both Jackson and Oliver nodded and the cards were dealt. No one wanted to have their dicks sucked and they really didn't want to suck someone else's (right?). "And by the way, for all of our sake's, this will be the last hand, okay?" The others eagerly agreed.
It all came down to this hand. If Oliver won, it would somehow be a repeat of the last turn. If Jake won, he knew Oliver may fold just to get rid of the raging hard-on he had in Jake's tightie-whities. Finally, if Jackson won, well nobody really wanted Jackson to win.
Everyone looked at their cards. Oliver made some kind of a face but quickly corrected. The other boys saw it but didn't comment. The cards were exchanged with the dealer. "All right guys, it's time to show your hands," Jackson said. He prayed to win, if only to get out his cum-soaked briefs. None of the players wanted to put out their cards first.
Oliver decided to just show his cards. "Screw it…." He commented as he placed his cards down on the table. A full house.
Jake cursed. "Damn it!" He put his cards down. A straight. Oliver sighed inside. Jake looked at Jackson with cocky eyes. "Like you said, it's time to show your hands."
Jackson sadly put down his cards before putting a grin on his face. A straight flush. He would have gotten up to do a little dance but his hips were a little sticky. Oliver looked at Jake while Jake looked away. Jackson stood up and, turning his dick away from the other two and standing behind the piano, stepped out of his cum soaked briefs.
No one wanted to fulfill the bet. Jake looked at Jackson and the piano again. "Last time. High card draw," Jake said, taking the pile of cards with him to Jackson, "I pull high card, the bet's off and we put all of our clothes on and walk away like this night never happened. You pull high card, the bet stays the same."
"Jake, you know how this works. He's not gonna pull unless you raise the stakes," Oliver chimed in, rolling his eyes. Jackson nodded his head in agreement
"Fine. You wants the stakes raised? I'll raise them all together," Jake said coolly, "You pull high card, the bet stays the same but I lose the boxers in the process. You would see all of my junk and judging the erection you had earlier you wouldn't mind seeing it." Jackson's face told nothing. "I pull high card, the bet's off, Oliver and I put our clothes on and walk out of here like nothing happened but you have to stay naked for the next day when your dad and sister get home. Wadda say?"
Jackson, after a second, agreed. "This is not going to end well," Oliver thought. Jake pushed the cards towards Jackson. Jackson shuffled them and pulled the top card. 7. Oliver prayed Jake would beat it and they could walk away. Jake took the top card. 2. Jake hung his head in defeat as he walked back over to Oliver. He stepped out of the boxers and they both got a nice look at his dick. 9" round and somewhat thick, it looked nice surrounded by his blond pubes. Oliver's was still just as thick as before but 8" now and looking very manly among his dark pubes.
Oliver, now out of his tightie-whities, stretched his legs. "It needs some air," he explained. He realized he could procrastinate no more and walked over to Jake. Dropping to his knees, he stared at Jake's dick. If it was possible he was getting harder just looking at it. He put his mouth around it and slowly but surely started blowing one of his best friends- Jake.
Jake didn't think he was going to like this. Another guy sucking him off? But when he saw Oliver on his knees, he was surprisingly turned on. Then, when Oliver began sucking his cock, he went into a whole new realm of pleasure. Standing there, he didn't even care that he was naked. All that he cared about were the hot lips giving him a blowjob.
Jackson couldn't believe. His two best friends were sucking dick right in front of him!! He should be grossed out by the sight but by the erection he was getting and how quickly he was getting it, he was definitely getting aroused by it!
Jake couldn't even think straight. Heaven was on his dick. Hi could feel Oliver's tongue on his head and in his slit. Oliver would only stop when he couldn't fit any more into his mouth. It felt amazing. He put his hands through Oliver's hair and started face-fucking him. "Oh god Oliver! Oliver!"
Oliver started and stopped, quickened and slowed, just like Jake had done to Jackson but differently. Something was in his mouth after all. He felt Jake pushing harder and harder into his mouth but he didn't care. He could feel a bit of pre-cum on his dick though. It didn't matter. All that mattered was pleasing Jake.
Jackson had a full-on hard-on now and he didn't care that it was from watching his friends sucking dick. He began masturbating and could feel the orgasm coming.
"Oliver, you're amazing!" And, on that note, Jake came all over Oliver's mouth. There was so much of it that some slipped out of Oliver's mouth. Jake pulled out, done. Remembering how roughly Jake had pulled his hair when groping him, he pulled Jake's hair and kissed him back.