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Bet Gone Bad (JennaRP & LustfulSins)

Casey was barely awake as he came down from a second orgasm. He’d never had two in a row and felt absolutely depleted, the exhaustion mixing with the drunkenness, he just wanted to close his eyes. So he groaned in passive resistance as he was maneuvered about once more. His eyes barely slitted open as he looked down, seeing a long, thick cock hanging off of Max.

“Hmm mmm. D-don’t” he tiredly complained as he felt the prodding at his ring. He tried to clench, but with how he’d already been stretched and how weak he felt, the cock popped inside him. Feeling Max shift for better leverage as Casey was stretched and filled with cock. He squirmed some, complaining as Max continued to push and coax him to take it all.

He felt Max’s full balls resting against him as his roommate buried his entire length inside. His asshole throbbing, gripping and massaging the shaft as his walls spasmed with the foreign intruder, all of his squirming just making him grind on the cock.
 
Max groans with Casey's movement, hips pressing harder against the boy. Then his hips draw back, only to press forward to the hilt again. Max sucks in a sharp breath at the friction. And just like that, he picks up a steady rhythm of back and forth. Each thrust is strong, Max's hips bucking against Casey.

Max curses, leaning low over his roommate. His breath is hot on Casey's neck, hips rutting steadily against the boy, every motion burying his cock deep. In the back of his mind, he's wondering why he didn't do this sooner, instead of the weeks spent masturbating in the shower and at night. This is so much better, buried inside Casey's tight body.
 
There was a part of Casey that was mortified, aware that he was currently being fucked in the ass by his roommate. But that part of his was quarantined away, unable to break through the foggy haze that was Casey’s world. His body rocking, ass jiggling with each hard thrust into his ass. His cock almost begrudgingly becoming hard once more as Max hammered in a deep and hard rhythm.

The throbbing had mostly subsided, for now at least. He’d be in for quite a rude and sore awakening when he finally came back around and was sobered up. But for now, his hands just listlessly rested on Max’s wrists, as if holding on for the bumpy ride he was taking on his roommate’s cock.
 
Max shifts the angle of his hips, hiking Casey's legs higher up his waist. This new angle allows Max to strike and rub his thick cock against Casey's prostate. When the boy reacts to that, Max's thrusts increase in power, until he's rutting hard against his roommate. Groans fill the air, and Max leans on his forearms to either side of Casey's shoulders to better support himself.

After almost ten minutes of hard fucking, Max finally hits his orgasm. His stamina is impressive. Bucking hard, Max buries his cock to the hilt with a grunt. Another loud groan is pulled from him as his hot seed pours into the depths of Casey's body. Max's hips jerk tightly through the aftershocks of his orgasm.
 
Cary groaned as his legs were forced higher, his ass raising up for Max to truly ram and rut into. Casey’s legs still in the stockings, toes curled as his prostate was rubbed relentlessly for what felt like an eternity. His moans growing louder as his orgasm was brought along during the fucking, Max’s shift in position making his cock start to ooze what little precum had time to build back up.

They came together, more or less. Max’s strong stream painting Casey’s insides, filling him up with a load of cum as what little he had left spurted from his own cock. His eyes rolling back in his head, never having felt so exhausted, sure to wake up with a hangover and a lot of questions.
 
Breathing increased, but not hard, Max rolls off Casey, cock pulling from the boy's body. Casey's muscles would spasm and try to return to their normal position, so Max's seed would likely spend most of the night inside the boy. Tired himself, Max tosses one arm over Casey, pulling the sheets to cover them. It's nearly 1am, and Max falls asleep quickly.

Come morning, Max is the first to wake. He had rolled himself right up against Casey, and he's sorely tempted to just start a morning round of sex right then, before Casey is awake enough to push him away. One hand trails along the boy's skin, even dipping briefly between his thighs. But Max shakes his head, pulling away and leaving the room. He returns briefly to set strong painkillers and a glass of water on the bedside table.

In the kitchen, Max makes coffee as he thinks about the previous night's events. Dressing Casey like a whore, getting him drunk, winning the costume contest, then bringing him home and fucking him. Max shudders. There's no way he's going to let that be the only time. He sees this as a turning point in their relationship, and plans to train Casey's body to his touch, so that the boy's lust and pleasure overrides his inhibitions about being fucked by a man.
 
Casey’s eyes opened briefly as he felt Max moving, but they quickly closed from the pain of the sun shining in. Why was Max in his room? Why did his bed feel so weird? What was he laying in that was cold and damp?

He remembered bits and pieces from the previous night, but hardly anything after the cosmo at the club. Some of the shots, very little of the contest and surely not what happened after. He squinted again and saw that he was actually in Max’s room, but he still wasn’t putting it all together. He saw the pain meds and water on the nightstand and assumed it was for his headache. Max was the considerate one, probably just taking care of him when he came home wasted.

As he sat up and downed the pills, things started to clear up as he rubbed his eyes. He looked down at the stockings still on his legs... but nothing else. That was definitely surprising. As he scooted towards the edge of the bed, he saw the wet spot under his ass. Did he drunkenly piss the bed?!

But, as he stood up, things really took a turn. His ass ached like he’d never felt before, instinctively reaching back and feeling... something sticky. He brought it to his nose and it instantly crinkled at the smell of... cum? His cheeks suddenly a deep red as he tried to come up with some way that it could make sense, but he was drawing a blank. He could hear Max moving in the kitchen and, in his haste, only saw the dress on the ground that he stuffed himself back into before walking out. He didn’t know if he should be mad, he didn’t know how it all happened. He needed answers.

“Oh... hey” he stammered as he walked into the living room, hands covering his crotch as the ragged dress cling to him, cum starting to leak from his ass from the movement. “What, uh... what happened last night?” he asked, obviously meaning he wanted to know just how he wound up in his roommate’s bed in a puddle of cum.
 
Max turns around when he hears Casey's voice behind him. Seeing the boy back in the dress, and without the thong this time, makes the blond's stomach clench. Then he's asked what happened, and a slow smirk spreads across his face. Max lifts his coffee mug to his lips, taking his time responding.

"What do you think happened?" Max waits. He wants to see if Casey can put two and two together, and how the boy would react. So he waits, gives Casey time to process his thoughts. Meanwhile, Max is looking the disheveled boy up and down, silently wondering when he can mount him again.
 
Casey tried to study Max’s expression as he didn’t outright answer the question. He saw the stack of cash on the table, which surely meant they won the contest. Maybe... they brought a girl back for a threesome? That seemed to be the best case scenario of how cum wound up on his thighs and... inside his ass.

To try and avoid actually speaking about it, he turned his back to Max and bent slightly to grab the cash off the table, the dress riding up to expose his backside as he did so before he realized it and straightened back up. “Well, it looks like we won the contest. I think I.. earned this money” he said with a hard swallow. “I don’t remember much after the shots at the bar. Did we stay at the club long? Did anyone come back here with us?” He was grasping at straws now without outright asking his roommate if they’d done what he feared they’d done.
 
Max is amused by Casey's refusal to admit he has perhaps figured it out. So when the boy turns his back and scoops up the cash, Max sets his coffee mug down and comes up behind Casey. His arms wrap around him, pulling him flush back against his body. One hand slides down over the boy's groin.

"Nobody came home with us. We fucked, Casey. Or rather, I fucked you. And it was so hot, you came three times. You begged me not to stop." Max bites Casey's ear, his fingers sliding down Casey's soft length, then dipping between his thighs. His palm squeezes the boy's sac gently as his fingertips brush Casey's messy hole.
 
Max was on him before Casey could turn around, pressing into him and saying they fucked. Or one of them fucked... Casey was fucked. And, the ease with which Max said it and how he freely groped Casey made him sure Max was telling the truth. But surely he hadn’t cum three times.

“You’re lying” he said, no conviction in his tone as he tried to twist out of Max’s grip. “You set me up, feeding me all those drinks all fucking night” he said, the bitchy and defensive tone in his voice now.
 
Max tightens his grip on Casey, licking his jaw. One finger rubs at Casey's hole, and the boy's twisting just has him grinding back on Max. "I may have encouraged your drinking. But once we got to the bed and you learned the pleasure I could give you, you didn't fight. You moaned, spilled your seed, just as I spilled mine inside you."

Max turns them, pressing Casey up against the back of the couch, hands bending him forward slightly. His hips grind firmly against the boy's ass. "Perhaps I should give you a reminder?" Max licks his right finger, now sliding his hand over the curve of Casey's ass to press it into the boy's entrance. The remaining evidence from the previous night, which Casey had yet to clean up, aids in the slick slide of the blond's finger.
 
Casey let out a small yelp as he was turned and bent over the couch. The finger moving to his ass, pressing inside as the cum still inside made a squelching sound, his clenching doing nothing with the cum aiding as a lube. He was still in the dress and stockings, face a mess of makeup and sweat.

Suddenly a flash of a memory coursed through him. Legs bent back, watching Max’s thick cock pushing inside him. As he remembered, his cock began to grow as he was pinned to the couch, trying to wiggle away before Max noticed. “Max... no... don’t” he whined, though his legs were subconsciously moving wider, back starting to arch as his body craved that feeling again.
 
Max adds a second finger almost immediately, left hand planted on the small of Casey's back as he starts to arch. Max is mildly impressed; Casey's body is already craving that feeling after only one night. "No? But your body says yes. You're already spreading and arching."

It takes very little time for Max to locate Casey's prostate this time. But he intends to remind Casey fully of the pleasure he experienced the previous night. So his fingers massage the boy in a rise and fall; lifting Casey to the edge of orgasm, only to halt and stroke at the biy's inner walls when he gets too close, denying him that bliss.
 
As the second finger slid in, Casey couldn’t help but notice that it was an oddly familiar feeling. Some burning, but not near enough for it to be the first time... but maybe that was just the pain meds?

As Max hit his prostate, though, a flood of the memories rushed in. The sensation of the intense orgasms, how good the release felt, all of that potential coming back in his head and it caused a deep, slutty moan to leak out.

“Max... Max come on... we can’t” he moaned again, helpless to stop it now as he knew he wanted to feel that cock back inside his ass.
 
That moan makes Max's cock leap to life, twitching in the sweats he's wearing. He wants to hear more moans like that. Like last night, Casey is protesting. But this time, his protests are coupled with sweet moans. "Why not? We're both adults, we're both horny, and we're not allowed to have the opposite sex in our apartment. Not that I need the opposite sex when I have your tight ass."

More rise and fall, more stimulation followed by the let down. Max knows he's creating sexual frustration in Casey, but it would result in an orgasm that much more powerful. "I will have you, Casey. I will have you whenever and wherever I want. And you won't run away. Admit you want this. Admit you want my hard cock filling your ass."
 
Max was obviously determined to drive Casey mad with arousal, and even with Casey aware of that, it was working. His tight ass had Max’s attention, and now that he’d fucked his roommate once, he seemed to want to do it again.. whenever and wherever he wanted.

Casey was trying to resist, really he was. But the constant edging, being so close to cumming all over the couch he was bent over only to be eased off over and over again, it wore on him. “Ok.... ok, just... just one more time” he said through a particularly loud moan. He couldn’t believe he was accepting this, sober and still in the dress and stockings. “I... I want your h-hard c... cock in my ass” he said as his asshole clenched around the fingers.
 
Max smirks, leaning over the bent boy to lick the side of his neck. He straightens, removing his fingers, and pushes down the front of his sweats. "Good boy." Max lines up, then presses forward, faster than the previous night. He sinks his cock to the hilt, groaning, hands gripping Casey's hips.

This time, Max doesn't wait for Casey to adjust. Immediately, his hips start rolling and bucking, thrusting into his roommate. Yes, he could definitely get used to fucking Casey. Especially when it's so easy to make him give in. After only one night, Casey's body already reacts so sensitively.
 
Casey asked for cock... and Max quickly obliged. He felt the tip pushing into his still gaping hole, pushing in deep with one hard thrust that lifted Casey to his toes without the heels to already put him there. His hand gripping Max’s wrist on his hip as Max wasted no time in settling into a hard, fast rhythm. “Oh... fuck... wait... s-slow d-down” he stammered, though his body was loving the rough pounding.

After just 30 seconds or so of it, Casey was sure Max wasn’t lying about how many times Casey came from being fucked last night. Already his cock was oozing precum onto their couch, bending over and spreading his legs wide to be fucked as hard as Max wanted. “Right there! Oh shit... I’m gonna cum” he called out as he was milked of his fresh cum onto the cushion of the couch he was bent over.
 
Max doesn't slow, hands gripping Casey to support him as he ruts against the boy. The mix of Casey's words and moans only urge Max on. And when he hits his climax, Max groans loudly as the boy's muscles clench around him, but he doesn't stop.

The air is filled with the sound of moans, groans, and skin hitting skin as Max thrusts hard into Casey. Max can definitely see this becoming a regular thing, and Casey would most certainly come to crave it. Max bucks hard particularly hard again, growling at the boy moaning, bent over the couch.
 
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