A Risky Midnight Encounter

"Yeah, the place Anna's dad is renting us is in the Bay area, it's gonna be awesome. Way nicer than any shitty apartment around here, huh?" Tony's coworker bragged, leaning against the back counter.

"Uh-huh," Tony said. He was wiping down the soda machine for a third time, just trying to keep busy until 3 o'clock.

"We still good for tonight, bro? Like I said, my parents are gonna come get me tomorrow morning, but they're stuck back home all night tonight."

"Yeah, Jake. My roommates are cool with you staying over as long as you don't snore, the walls are thin as fucking paper in the new place."

Jake laughed. "That blows dude, I bet you wish you were moving out to Cali like me and my girl. But it's tough out there, it's not for just everybody, you know?"

"Right, right. Maybe someday," Tony tried to sound like he was just joking around, but Jake was fucking annoying... why did he agree to let him sleep over? Just then, the door to the shop dinged as someone walked in from off the street.

"Oh hey, how can I help you?" Jake said, walking over to the counter to help the customer. As he walked, his impossibly thick bubble butt jiggled around in his khakis. Right, Tony thought to himself, that's why. And his face wasn't bad either. Kind of a waste of all that on a straight guy.

Tony casually watched Jake pack up the customer's order and ring them up. By then, it was just about 3 o'clock. Tony walked to the back to clock out, then grabbed his backpack to leave out the main entrance.

"See ya tonight Jake, just text me if you can't find it," Tony called out as he walked out the door into the hot summer afternoon.

At home, Tony cast his backpack on the floor and laid back on the couch, pulling out his phone. At some point he dozed off, but he was soon awoken by the front door slamming.

"I'm home!" Maddie called, then appeared from around the corner. "Oh, it's just you, Tony?"

"Yeah," Tony said, yawning. "How was work?"

"Fine, fine. As usual, the most exciting thing was watching my coworkers argue about where to go for lunch." Maddie sighed. "I'm gonna go wind down, though, so buh-bye for now."

"See ya. Also, Jake from work is sleeping on our couch tonight."

"Right, right. As long as it's just tonight, I don't want another cishet roommate. Nathan bothers me enough already," Maddie stuck her tongue out at that, before turning down the hall.

Tony flicked some random movie on TV, determined to not fall asleep again. It wasn't long before he received a "Omw" text from Jake, who showed up shortly after.

"Not a bad walk," Jake grinned from the doorway, kicking off his shoes and piling up his bags next to the couch. Sitting next to Tony on the couch, their size difference was noticeable. Jake's long legs had to fold to fit between the couch and coffee table, and his head brushed the wall while Tony reclined comfortably in the same space. Jake always talked about playing basketball in high school, but Tony hadn't ever told Jake he had been on the girls' volleyball team.

The thin fabric of Jake's shorts rode up and strained against his wide thighs as he shifted to the edge of the couch and grabbed a drawstring bag.

"Hey, I've got my bong wrapped up in here, wanna smoke? My treat for you guys letting me stay."

Tony nodded, with no other plans for his night, and he and Jake burned through two deep bowls before the movie ended. A little while later, Maddie came out to pick up her Thai food delivery, but declined the hit Jake offered her and rushed back to her room. Their other roommate Nathan arrived home halfway in to the next movie and accepted Jake's offer to join in the festivities.

The guys stayed glued to the couch for the next few hours, giggling at stupid moments from whatever garbage Nathan had added on his Netflix watchlist. Jake had scooted closer to Tony to make room for Nathan, and in the low light Tony felt his cock twitch as he took in Jake's unshowered man scent warm and moving right next to him. As Nathan clicked from one episode to the next, Tony found himself glancing over Jake's body again and again.

Before long, Nathan stretched off the couch and headed to his room, and Jake started yawning. Tony wasn't tired yet, but he took pity on the guy. He'd planned anyway to stay up and grind some levels on the computer before going to bed in the AM hours...and maybe jack off for a bit, too. With that in mind, he passed Jake the remote, and went around the apartment turning off the last of the lights.

"I can grab some clean sheets for you, but you'll have to sleep on one of the throw pillows. Also, no one's figured out how to turn off the stove light, so you'll have to deal with that."

"I've dealt with worse," Jake said lazily, slurring his words as if he were already half asleep. He paused. "You think Maddie likes me?"

Tony couldn't help but laugh out loud. "You're kidding, right? She couldn't get away from you quick enough. It's like you repel women."

"Damn, I hope not. It's whatever, I don't go for girls with dyed hair anyway."

"I bet you just like girls who put out whenever you ask," Tony replied.

"Do you put out whenever a guy asks?" It was impossible to read Jake's expression in the flashing light of the TV, but that had to be just another joke. Right?

"I bet you'd like to know," Tony said, playing it cool even though his heart skipped a beat.

"I'd fuck you, if you were a girl." Jake said confidently.

"Yeah?" Tony tried to chuckle, tried to stay nonchalant, but fuck if that didn't turn him on. "What about Anna, you gonna leave her for me?"

"Hahah, cute, you really think I need to dump her to fuck someone else?" Jake replied with a laugh. He really was an asshole. Tony's dick was throbbing anyway.

"Whatever, dude. I'm going to bed." Tony ducked into his room to grab a stack of clean sheets from his closet, tossed them blindly towards the couch, and closed his door without another word.

*********

An hour later, Tony's cock was in between his slick fingers as he pictured Jake railing him. He'd already cum once, but his cock had stayed hard since the first movie he'd watched next to Jake. Had there been some aphrodisiac in that weed or something?

His hand was starting to cramp, so Tony rolled on his back, catching his breath while his mind was still clouded with lust. It was so hard to cum without a dildo, and Tony cursed his ex for keeping them all when he kicked Tony out. Regardless of that asshole, Tony's front hole was still wet and ready for a toy, and a thought occurred to him. There was a dildo, loosely speaking, waiting for him in the living room. The cock he so desperately thirsted for was within reach. But how would he get it without waking Jake up?

As if on cue, a rumbling snore came from the other side of the wall. Well, that was as much convincing as he needed.

Tony leapt up from the bed, his heart racing again. He still had a t-shirt on, but didn't bother to put on his boxers or sweats so he'd have easier access. Tony shut off the lights in his room and waited for his vision to adjust, mentally preparing himself for what he was about to do. After another couple snores, he gingerly opened the door and stepped out into the kitchen, where the soft light from the stove illuminated the adjacent living room.

Tony crept into the next room, feeling his wetness grow with each step. Even in the low light, he was able to make out a decent bulge under the thin sheet Jake was sleeping under. Maybe he even sleeps naked, Tony thought with a shiver of desire. No boxers, please, no boxers...

Up close, Jake looked douchily carefree as ever in his sleep. His head rested on a folded arm, while the other arm hung at his side. His black t-shirt rode up and exposed a thin dark happy trail as Tony pulled the sheets down to his thighs. Damn, boxers - but daaamn, the smell was pungent and intoxicating, since Jake hadn't bothered to shower after work. Tony swore to himself not to wash the sheets.

Before he could stop himself, Tony reached out for Jake's bulge - but his cold fingers brushed Jake's pasty white thigh, and he jerked in his sleep. Tony stumbled back, his heart racing, but Jake just rolled to the side and quickly resumed snoring.

In this new position, Jake's dick had shifted towards him, and Tony couldn't help but trace over his impossibly wet hole. Once his fingers were sufficiently warm and lubed up, he reached out to pull Jake's boxers down, just enough to see a thick forest of dark pubic hair. Arousal flooded between his legs as he pulled the waistband down further, and he gasped when Jake's huge meat flopped out.

"What the fuck am I doing?" Tony whispered, his heart thumping harder and faster. He sat back on his heels in his living room, naked from the waist down, and looked at his coworker laying clueless and unconscious on the couch with his penis exposed. Tony's head rushed with lust, fear, and cannabis. He took a deep breath.

"I'm...just gonna touch it." Just touch it, and then pull his boxers up and run to my room to jack off. Or touch it, and then taste it, and then run. Or...

Tony reached out, his hand still slick with his own wetness, and grasped Jake's fat cock gently. The snoring paused, and Tony froze, but Jake just sighed, and the next breath was another snore. He began to stroke up and down, slowly, but steadily gaining speed. Tony almost moaned out loud as he felt Jake's penis begin to harden in his grip.

Tony leaned over the couch and spit on Jake's cockhead, smearing it around gently. He leaned forward to spit again, but surprised himself when his lips parted and the tip of Jake's penis slipped into his mouth. Tony salivated at the hot musky taste, and generously bobbed his head back and forth to lubricate his unconscious dildo. With a soft moan, he broke away and pumped Jake's huge cock with both hands, keenly aware of the dripping heat between his legs.

It was the endless stream of hormones from his pussy that prompted Tony to finally let go of Jake's alpha cock and jerk off his own. He bit his tongue hard to restrain his moans as his hole pulsed and his entire abdomen burned with lust. If he was going to take that cock, it had to happen while he still had the nerve.

It took some silent gymnastics for Tony to arrange himself above Jake on the couch, but with one leg on the back of the couch and one on the floor he felt like the object of his desire was finally within his reach. He angled his hips towards Jake's big dick, stifling a gasp when the tip brushed his hole, and...

...And slipped the head in. There was no going back now.

Slowly, keeping a close eye on his coworker's sleeping face, Tony sunk his hips down toward Jake's dark pubes. His heart pumped adrenaline and lust through his whole body with each inch.

Until, fuck, hamstring cramp. Tony's spine straightened, and he had jumped off Jake's dick before he even realized what he was doing. He held his breath, but the house remained silent, and Jake remained asleep.

Well, that wasn't going to work. Unless...

After assessing the situation, Tony planted a foot on the couch next to Jake's hip and slowly eased his weight over. Judging by how Jake's snoring didn't stop or stutter, this would be a breeze. Still, riding him in reverse Tony could only see Jake's legs stretched out under the sheets, and if he looked down all he could see was his and Jake's pubes blurring together in the dim light. He knew he should try his absolute hardest to stay quiet, but that thought went out the window when Jake's cockhead brushed against Tony's wetness.

Without wasting a second, Tony sat down on the fat white cock again, feeling his cunt gush as Jake's length rearranged his insides. He couldn't help but moan softly...he wished so bad that circumstances were different and Jake was pounding him into his own mattress. But here they were, Tony gyrating his hips on Jake's unconscious rock hard cock in the middle of the dimly lit living room.

All Tony's nerves were alight at once - his body tingled from his core to his toes as he lifted up, and again when he sunk back down and stretched his hole out once more on Jake's big dick. Each sensation was multiplied tenfold, from the scent of Jake's fertile, sweaty balls to the pressure of Jake's thick cockhead against Tony's cervix.

But he hadn't noticed the snoring stopped. Focused as he was on not making a sound, Tony almost screamed when he felt two hands grab his waist.

"So does all gay guys' ass feel like pussy?" Jake slurred, still half asleep but clearly aware of the situation. "That's fuckin' awesome, I should try this again sometime." Even in a low tone, his deep voice was impossibly loud in the silent house.

"Shh," Tony warned him, but the warning didn't come off as serious, since he was still sliding his hole up and down on Jake's cock.

"You like it like this, don't you? And I thought I was messed up." Jake whispered as he started pushing into Tony's thrusts, his bare cock hitting deeper and deeper inside Tony's vag. "Let me guess, you wanted my straight boy prick so bad, you just went and took it?"

"Mhmm," Tony groaned, rubbing his own cock while Jake was bottoming out inside him.

"You're a dirty man slut, huh?"

Tony just moaned loudly.

At that exact second, a light flicked on in the first room down the hall - Maddie's room. Tony stopped moving immediately, but Jake kept pumping into his cunt, running his hands up and down Tony's hairy thighs.

"I bet you want her to walk out and catch me inside you, huh? She'd think I took advantage of you and made you fuck out here instead of in your room," Jake said in a low, husky tone. "She wouldn't guess you were the one who came out here to fuck me. It's like you wanted to be caught."

Tony gasped and started rutting his hips on Jake's dick.

"That's it, then? You came out here naked to fuck a sleeping straight guy, all cuz you wanted your roommates to see you getting fucked? Wanted them to catch us with my cock eight inches up your ass?" Jake asked. Tony whined, and his cunt pulsed when he realized their lustful sounds were definitely loud enough for Maddie to hear through the door.

"You're such a whore..." Jake continued, "More than any woman I ever slept with. You didn't even consider using a condom, I bet. You just wanted to feel my raw jizz filling your fag hole."

"Yes," Tony gasped, his pussy getting even wetter at the thought, "please yes, Jake, I need it..."

"And you're gonna get it, cunt," Jake said as he grabbed Tony's hips and began slamming his hole harder than before.

"Fuck yeah Jake, fuck my pussy," Tony whined, not even trying to hold back anymore.

"You want my cum, babe? You wanna make a baby together?" Jake grunted. Tony didn't even care he was talking to him like he'd talk to a girl, in fact, it was kinda turning him on.

"Oh fuck, Jake, give me your baby, I want your cheating cum!"

Jake groaned, and grabbed Tony in a bear hug from behind as his alpha cock pumped fast and deep inside Tony's cunt. Tony's eyes rolled back in his head when he felt Jake's cock pulse inside him, and he realized he was getting bred raw. He was so close to cumming, too, so close, and then -

The door creaked open.

"Hey, have you guys seen my glasses - oh my god!" Maddie screeched, and slammed her door shut. Tony jumped off of Jake's cock in an instant, with cum already beginning to drip out of his hole. Before Jake could turn on a light to get a look at his body, Tony ran back down the hall to his room and shut the door, heart pounding like mad.

"Fuck." he said out loud.

Tony flopped down on his bed and looked at the mess of wetness between his legs. Jake sure did cum a huge load...maybe...maybe...

He scooped out a fingerful of cum and rubbed it on his small cock. The feeling of another man's cum fresh inside his pussy combined with the adrenaline from being caught was turning him on so much. Tony spread his legs, angling his cunt toward the door. He closed his eyes and fantasized about Jake suddenly opening the door and seeing he'd just fucked a man with a vagina. All too quick, Tony came with a groan, and the fantasy disappeared as he fell asleep nude on his bed.

*********

Tony awoke to the sun streaming through the window, illuminating his cluttered room and the mess he'd leaked out onto his bed. Memories of the night before came rushing into his head, and he quickly straightened his hair and pulled on some pants before heading out into the kitchen.

Alone at the dining table, Maddie looked up at him over eggs and toast. Her eyes widened almost imperceptibly for a second, then she cleared her throat.

"Good morning, Tony," she said, looking down at her phone.

"Morning," he yawned, walking past her to the pantry. "Hey, did Jake leave already?"

"Yup, his parents picked him up around 9," Maddie replied, eyes never straying from her screen.

"Okay, cool." Tony selected a half-empty bag of granola and some fruit, then headed back to his room to eat in a less awkward environment.

"Oh, and Tony?" Maddie said innocently, looking up to meet his gaze when Tony was halfway through the door.

"Yeah?"

"He said to call him if you end up pregnant." She smirked. Tony slammed the door and collapsed on his bedroom floor, face flushed.

Well, shit.

Across the room, his phone buzzed -

Jake from work: "Hey thanks for last nite. I'll lyk when I'm back in town ;)"