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Bet Gone Bad (JennaRP & LustfulSins)

Having Casey lean against him would work very well in acting out their costume. Speaking of, the DJ is calling everyone. Max tips his head back to finish his whiskey, then down a shot. There's one left, and Max gives it to Casey. Soon as he's swallowed it, Max is guiding Casey to the stage, arm around the boy's waist.

They're the fifth pair to be called. As they walk out onto the stage with the previous four, Max runs his hand along Casey's side in a way that draws attention to the boy's hips as he walks. And with Casey being the 'centerpiece' of their paired costumes, Max pulls the boy to stand in front of him when they stop to face the crowd. His arms are around Casey, one circling his waist, the other draped against his hip and palm pressed low on his abdomen. "Smile pretty, Casey. We're going to win."
 
Casey found himself walking to the back, guided again by Max. He felt the hand on his waist directing him as they took their spot in line. Girls were dancing on men or doing sexy little dances to get the crowd going. Casey felt his heart racing as it was their turn, Max telling him to smile pretty. Had he not been completely wasted, he probably would have made a run for it... but the liquor in him made him foolishly brave.

So he walked out, the crowd cheering at a new high as they easily were in the lead. “Looks like we have a hooker and her pimp?” The DJ called out as Casey gave a spin. “Cmon baby, give them more!” the DJ shouted down to Casey. Again, the alcohol took hold as he began to grind his backside against Max behind him, leaning forward and doing a halfway decent job of making his ass twerk as the crowd stirred into a frenzy.
 
Max is so glad Casey is drunk, because there's no way the boy would be grinding on him sober. The crowd cheering makes the blond smirk, and his hands grip Casey's hips. He even thrusts his hips lightly against Casey's ass a couple times, earning a fresh wave of cheers. When Casey stands upright again, Max slides his right hand down Casey's chest and stomach,and further, even briefly sliding his fingers under the terribly short hem of the dress. The crowd practically screams, and Max gets a light scolding from the DJ.

Max is laughing and deeply enjoying himself, even keeping his hands on Casey. Though now, one is on his hip, the other on the boy's thigh. His thumb is brushing back and forth across Casey's exposed skin above his stocking. The DJ is announcing the runners up, third and second place.
 
A sober Casey would have crawled into a hole with all that was going on... but drunk Casey appeared to love the attention. Even as Max ground into him and let his hands wander, Casey took it all as part of trying to win the contest. He was just playing a part, in his drunken mind, so he even kept standing back against Max as the runners up were announced. When Casey didn’t hear their names announced, he knew they’d won.

“And our winners, with no surprise, are our pimp and his ho!” the DJ shouted, the two being ushered back up to the stage as the crowd encouraged them to head up. “Looks like that is... Max Grayson and Casey Dawes. Let’s hear it for the winners!”

Casey froze for a moment as his name was broadcast to the club. Anyone that had even had a class with him would surely be looking, examining the two. He surely wasn’t the pimp... which only left one conclusion. Casey was trying to slip off the stage, but the crowd was in close, forcing him to stay up there, drunkenly dancing with Max.
 
Max is grinning when their full names are announced. A little bit of humiliation, maybe? Just like the crowd, Max doesn't let Casey escape. His arms wrap around the boy, and the stage turns into one massive bump and grind dance. Max is moving as well, hips rubbing against Casey's ass as he holds the boy to him.

"You did so good, Casey. Your little act definitely cemented our victory." Max's lips brush Casey's ear, his breath warm. They dance like this a while longer, until there's an opening in the crowd. "Let's get one more round of shots before we go home." Max guides Casey back to the bar, waving down the bartender. When the shots arrive, Max is more than encouraging, and ends up getting Casey to drink five of the six shots. Should be enough to tip Casey into being very easily suggestible.
 
Casey’s sober mind was trapped in the deep recesses, only his drunk actions making it through. So, as Max ground against him, Casey let it happen. The crowd was cheering and getting in his head, even as they went to the bar and they chanted for the hooker to drink the shots. He was running on autopilot, unsure how he was even awake still as he finished the shot.

“H-home. Need to g-go home” he stammered in his slurred speech to Max, resting his head on the man’s shoulder as the drinks were taking over. He just wanted to close his eyes for a bit.
 
Max grins when Casey slurs. He wraps his arms around the boy, easing him through the crowd. They're still cheering as Max collects the two hundred dollar prize and ushers Casey out the door. The crossdressing costume had been a huge success, and max is thrilled to learn what a lightweight Casey is. He loads his roommate into the car, pulling away from the club. "You did so good tonight, Casey. Everyone loved you." Max's hand lands on Caseh's thigh as he drives.

Once back at the apartment, Max supports Casey on the way down the hall to Max's bedroom. He lays Casey out on the bed, taking off his heels, then removes his own jacket, tie and shoes. "You look so hot, Casey."
 
The world was spinning as Casey was led out of the club, the cool air feeling good on his warm, rosy cheeks. He walked and was helped heavily to the car, collapsing into his seat. He barely even registered the hand on his thigh as he closed his eyes for the short drive back home before he was again climbing out.

He didn’t notice that they went to the wrong bedroom, though he did seem to moan softly at how much softer Max’s mattress was than his own. He could feel the heels come off as he laid there, the dress having ridden up to show the entire satin thong under the outfit as Max talked about how hot he was.

He let out a laugh, his drunken brain unable to understand the situation he was in. “Mmhmm... hottest hooker on the block” he said through a giggle.
 
Max bites his lower lip, kneeling on the Queen mattress beside Casey. His hands trail along the boy's legs, but he leaves the stockings on. His fingers explore higher, stroking the tops of Casey's thighs. Then he leans over the boy, left hand pressed into the bed.

Max doesn't hesitate any longer. He leans down, pressing his lips to Casey's. The second the boy gasps, Max's tongue slides into his mouth. Max groans, tasting both Casey and alcohol. His tongue explores the boy's mouth, slipping against Casey's tongue.
 
Casey’s eyes remained closed, even as he felt the weight shifting on the bed. When his eyes slivered open, he saw Max leaning down. “What-“ he started to say before his lips were pressed against Max’s. The moment he opened his mouth he felt the slippery tongue push inside, controlling the kiss and sliding around inside his mouth.

“Hmm mmm” he grunted, though he wasn’t coordinated enough to get away from the kiss. It didn’t process to bite or do anything aside from just wait for the kiss to surely end in a moment so he could tell Max to stop.
 
Max mistakes the attempt at speech as a moan and maintains the kiss. His right hand slides up over the dress to Casey's ribs, fingers playing with the slits in the dress. Eventually, Max cuts off the kiss, when Casey is breathless and panting.

Max doesn't stop there. His mouth moves, pressing hot kisses along Casey's jaw and throat. His fingertips rub the boy's skin through the slits in the dress, before moving down again to cup his groin. His palm rubs against Casey's cock through the tiny white silk thong.
 
Casey could barely stay in the moment, forgetting where he was as Max broke the kiss and moved down to kiss his jaw and neck. He squirmed some but not enough to get up, more just wriggling under Max’s touches.

When his groin was cupped, it was a shock. He let out a gasp and, if sober, would have pushed Max off of him. Would have stormed out and hell, perhaps filed a harassment report with campus police. But drunk? He couldn’t even put it all together.. his body just took over. This time he did moan, pressing his crotch into Max’s hand harder. “Mmm.. that feels good” he purred.
 
Max smirks, getting exactly the response he had wanted. Casey pushing up against his hand means he's drunk enough not to care anymore. Or at least not care enough. Max licks and sucks at Casey's throat, leaving little hickeys across his skin. His palm continues rubbing, until Casey is fully hard. Then his fingers hook the thin cords of the thong and pull it down his roommate's legs.

With Casey's cock now bare, and the dress pushed up just above his hips, Max strokes Casey's length. His teeth graze the boy's skin, nibbling. A quick adjustment of his balance, and Max's left hand comes to Casey's chest to rub one nipple through the thin pink fabric of the dress.
 
Casey was falling down this hole and there was nothing that would stop it now. His moans growing louder as Max continued, the panties pulled aside and a loud gasp as he felt a bare hand grasp his small, but rock hard cock. The rubbing of his nipple through the dress only making him start to grind his hips, as if trying to hump Max’s hand.

“Mmm, don’t stop. Gonna... cum... soon” he moaned, his eyes still closed as he was just becoming lost in the dizzy pleasure he was feeling in the comfortable bed. His body was taking over, pursuing that orgasm it was needing so desperately as his cock throbbed.
 
Max shifts tactics at Casey's words. His knees push the boy's legs wide, settling himself between Casey's thighs. His hips come down on his roommate's, and he rolls them firmly. His own hard erection rubbing through his slacks against Casey's cock creates a pleasurable friction.

Max groans lightly, soon sliding one hand between their bodies to open, then strip off his slacks. Once they're gone, he sheds his dress shirt. Then he resumes grinding against Casey, soft cotton boxers all that separates them now.
 
Casey could feel Max moving, adjusting their positions until it felt so good to have the friction rubbing against his cock. He moaned, his legs clasping around his roommate as he felt the heat increase, unaware in his drunken stare that his roommate was dry grinding their cocks together. Casey just knew he liked it.

“You’re so... big” he managed to blurt out, feeling something much larger and much harder than his own cock rubbing against him. It was a brief moment of clarity for him before he was lost in the pleasure once more, his hips grinding with Max’s. “Harder... need it... harder” he said as he was trying to hump Max’s erection.
 
Max groans again, pleased with Casey's drunken willingness. The blurted words almost make him laugh. At Casey's urging, Max does grind down harder. However, he also has other plans in mind.

Hips still rolling, Max slides his hands along Casey's body to remove the dress. Now Casey only has the stockings left on, and seeing him in only those makes Max's cock throb. The blond reaches for his bedside table, where a pump bottle of lube sits out in the open. With Casey's legs wrapped around his waist, Max moves his right hand down, rubbing lubed fingers between Casey's ass cheeks, arm easily reaching around and beneath the boy's lifted leg. Then he slides one finger into Casey's body.
 
Casey lifted his arms as the dress was pulled away, leaving him in just the stockings. He wasn’t even aware of what he had on, just going through the motions. He felt rustling as Max’s body weight shifted, then he was shifted himself. “What... what are you doing?” he asked, a bit frustrated that the grinding had stopped.

Then, the finger. Slippery and unexpected, Casey’s hands gripping at Max as it pushed inside his virgin hole. His back arched as it went deeper, his hole spasming around the intruder, his legs flexing at the feeling. “Hmm mmm... not... not there” he grunted, though he made no attempt to pull the finger away.
 
Max ducks his head to kiss and lick at Casey's throat as he works his finger back and forth. Max had figured Casey to be straight, so it's no surprise to him how tight the boy's entrance is. This is the point at which Casey might start sobering up, so Max needs to get him prepared to take his cock before he starts fighting back. Although, that might be hot, too, having to pin the boy down.

After a minute, Max adds a second finger. His hips grind down every few thrusts of his fingers, to make sure Casey stays hard. His fingers are spreading and curling inside the boy, stretching his muscles and rubbing at his inner walls. Being that Casey is an anal virgin, there's likely to be pain, even through his drunkenness.
 
As the second finger pushed in, Casey let out a small scream as his hole was stretched. The constant moving of them kept his hole burning, periodic waves of pleasure shooting through his body mixing with the pain. He was starting to try and push Max away, squirming and writhing under his roommate.

“Dude... nuh uh... no... mmm, fuck.. take them out” he groaned, all of his squirming essentially just having him grind on Max’s cock. He started to twist his body and pushed on Max’s chest to try and get him away, but he was wildly uncoordinated and weaker.
 
Max presses his weight down on the smaller boy, licking his jaw. Despite Casey's protests, Max persists, his fingertips rubbing and searching. He's looking for Casey's prostate, that little bundle of nerves that would send pleasure shooting through Casey like electricity. "Hang onto me. Bear with it just a bit longer."

Max has no intention of stopping now. He's hard, horny, and Casey is hot. Max rolls his hips to match the movement of his fingers, grinding firmly against Casey to distract him from the pain. He would know from Casey's reaction the moment he finds the boy's prostate.
 
Casey was bucking harder as Max tried to calm him down, the panic setting in that he had two fingers in his ass. “No... Max... don’t-“ he started, only to suddenly freeze, every muscle in his body tensing up and then jerking. “Ugh! Mmm fuck!” he squealed as the jolt traveled through his body.

He was still fighting, but much, much less. More just squirming with the fingers in his ass, his body craving that feeling again and again. Every time he’d let out a deep moan, his cock straining and nearly shooting his load at the sensation it caused.
 
Max smirks when Casey cries out, fingertips essentially massaging the boy's prostate. He's murmuring praises, head lifted to watch Casey's expressions. After a couple minutes of stimulating, and stopping when Casey seems too close to coming, Max adds a third finger.

Casey's entrance is stretched further, bringing pain again, but it's quickly subdued when Max returns to rubbing his prostate. Max's cock is throbbing, and he so wants to bury it in Casey's body and just fuck him hard. But Casey is a virgin, and he has to take his time.
 
As the third finger pushed in, Casey’s eyes clenched shut, his hands gripping Max’s body tightly as the burning felt like it was too much. At least until his prostate was rubbed again. The throbbing began to slowly subside, his hips grinding. He had no idea he was being stretched out for Max’s thick cock.

“How... do you know... how to do that?” he moaned, his cock aching for release. “Come on... little more... going to c-cum” he warned, being so close to the edge, he just needed a tiny bit more pressure.
 
Casey's confusion amidst his pleasure is a delight to watch play across his face. His question between moans makes Max chuckle softly. And when Casey asks for more, saying he's close to coming, Max's fingertips press firmly to his prostate, bringing the boy to orgasm instead of edging him more. He massages the bundle of nerves through Casey's climax, drawing out the feeling. He removes his fingers when Casey is relaxed and panting on the bed beneath him.

"My turn." While Casey is still riding the high of his orgasm, Max reaches for more lube, shedding his briefs. His hips lift, and if Casey were to glance down, his hard cock would be in full view. Nine inches of thick length, Max's fingers spreading the line along his sensitive skin. Then his left hand braces on the bed, right hand lining up his cock with Casey's entrance. His hips press forward, tip pushing past the ring of muscle.

Max sucks in a sharp breath. Even with his preparation, Casey is tight. Slowly, inch by inch, Max slides his hard thick cock into his roommate's body. At three inches, his right hand moves to the bed beside Casey's shoulder. Deeper, deeper, until all nine inches are buried to the hilt. Any protests are answered with encouragement to relax Casey's body. Buried to the root, Max holds still, groaning. "Fuck, Casey. You're still so tight."
 
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