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Pleasurable Revenge

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There was only so much of it he could take. Every single night his roommate would go out, pick someone up and come back to have loud, annoying sex and Castiel would have to put on headphones if he wanted any hope of sleep.

He had been trying to be a considerate roommate, to keep his own activities to respectable times and with consideration to Dean’s schedule, but after the tenth fucking night in a row Castiel had reached his breaking point. What was the point in being respectful if his roommate couldn’t be bothered?

If Dean wanted to go out, pick someone up and have headboard banging sex when Castiel was trying to sleep without a single care then why should he hold back? Why shouldn’t Castiel return the favor?

He’d been known as the town bicycle the second he’d discovered sex and it had continued through his entire high school career. Castiel had started young, in a house full of horny older brothers it couldn’t have been a surprise, and he’d discovered how much he loved being fucked. By the time he’d graduated he had already lost track of how many different guys he’d let fuck him and his virginity had been long gone.

Now he lived in a city, a city with a population in the millions, and there were plenty of potential one-night-stands he could bring back for a good time all the while showing Dean exactly how it felt.

Castiel didn’t even have to try.

He was in the bar less than ten minutes before he was propositioned by two big, burly guys who looked like they could break him in half. All it took was a glance down at their pants and he could actually see the outlines of thick, long cocks that Castiel knew would feel perfect splitting his ass open. The very thought of an enjoyable night that didn’t end with him listening to Dean fucking a one-night-stand had him practically shaking with excitement. As they left the bar he tried to remember the names they had given him but shrugged it off. It wasn’t as though it mattered. Castiel only wanted them for loud, enthusiastic and kinky sex.

Both followed him back to his dorm suite, Dean wouldn’t be back from his late class yet, and Castiel preened at the looks he was getting. There were plenty of appraising and interested looks but Castiel paid them no mind. For the moment. They could be used later to drive Dean insane if he didn’t want to go too far to find someone up for loud, wild sex.

He led both men into the suite he shared with Dean, stripping as he walked towards his room, while they followed along. No sooner had he opened his door were they on him. Castiel went limp, submissive and happily pliant in their hold. Considering the filthy promises they had made when they had first approached he was looking forward to whatever they planned to do with him.

“I want you to fuck me so hard the people two floors up can hear me screaming.”

They were naked in record time, pressing him into his mattress, while biting and licking and sucking as he writhed under them. It felt good, two warm bodies pinning him down and easily dwarfing him with their impressive bulk, as they played him like an instrument.

Castiel pushed up into them, moaning and whining, when his arousal built and his body heated with need.

He relished them manhandling him, one of them pulling him into their lap before splaying his legs wide to expose his tight ass, so they could prepare him. Thick, rough fingers coated in lube plunged into his dry hole causing him to wail loudly at the intrusion.

The man, it might have been Will, didn’t waste a moment as he started to finger fuck Castiel while the other man held him in place, kept his legs spread, so they could get him ready for the mouthwateringly big cocks both possessed.

My ass is going to be ruined.

The thought filled him with nothing but aroused glee. Each finger added had him jerking and shoving into them, trying to take the fingers deeper, before one brushed against his prostate and his moan echoed in the room. His hole clenched and his cheeks flushed darker as his arousal built.

“There it is.” The man grinned, scruffy face flushed and eyes heated, as he rubbed and rubbed against that spot until Castiel was sobbing with need and begging breathlessly for release. “Ready for my dick? Such a greedy little whore looking for two men to show you where you belong?”

“Yes! Please please please please.” He was babbling but Castiel didn’t fucking care. He needed to be full and he needed to be getting fucked into the mattress right fucking now. As though hearing those thoughts the fingers fucking him open slipped out and the whine that escaped at their loss earned twin chuckles.

“He really is eager for it. Little slut has probably been gagging to be fucked full.”

They manhandled him again, shoving him to his knees and pressing his face into the mattress, as Castiel eagerly let them position him. It would mean he was full sooner and that was what mattered.

Strong hands spread his knees out wide and shoved him until his back was bowed perfectly, ass raised and fingers clenched in the sheets near where his face had been shoved.

The creaking groan of the mattress had anticipation flying through him as one of the men moved up behind him, knees braced inside of Castiel’s to force them wider until he was whining in pain at the stretch, before the fat head of a cock pushed against him.

There was no easy pace, no gentle touches, as the man fucked that gigantic cock inside of Castiel with nothing short of greed. It was the kind of fuck that Castiel expected, hoped for because he loved mixing pain with his pleasure, when he went to a bar and the harsh burn of his ass spreading wider than it had been prepared for had him choking.

“Fuck that slut. Get that hole ready for me.”

Castiel keened at the feeling of his ass being forced wide as that thick cock fucked deeper and deeper until it was fully buried inside of him and Castiel was panting against the sheets. His eyes burned at the painful pleasure, his cock gone soft where it hung neglected, as fingers knotted in his hair and a thick hand gripped his hip for leverage.

Then the man was pounding into him. It was hard, fast, rough and near violent as Castiel’s body jerked from the force. Over the sounds of grunts, groans and the slap of skin Castiel could hear the protesting creak of the mattress and the loud banging of the headboard against the wall.

“That’s it! Use that ass.”

“Take it, whore, take my dick.”

Castiel would have made a comment that he was doing exactly that but all he could do was moan loudly and keen almost brokenly each time that cock nailed his prostate.

It was loud, filthy and there wasn’t a question that anyone with ears could hear them. Castiel hadn’t even heard the suite door open and shut until the other man snickered. “Think your roommate’s back.” But that wasn’t going to stop Castiel and he hoped Dean enjoyed being kept up.

Especially since Dean had a very early test in the morning and he’d planned to actually sleep tonight. It served him right.

Castiel made sure his moans were louder and louder as he was roughly pounded into. Heavy balls slapped against him with each thrust that drove the man fucking him balls deep, slamming his hips hard up against Castiel, as he chased his first orgasm. It was bliss. Pure, undeniable bliss. He let the pleasure of a good, hard fuck and the filthy dirty talk send him spiraling in pleasure.

It helped that he knew Dean wasn’t going to be getting any sleep. The same way Castiel had suffered multiple times despite his comments about Dean, maybe, keeping it down.

Finally, with a hard thrust, his current partner came with a loud groan as his hips jerked forward. Castiel’s ass clenched down, his body right there on the edge of orgasm, only for a hand to reach under and hold him off.

“You’re coming on a dick or not at all, little whore.”

The softening cock in him slipped out, sliding against his puffy rim, before it was being replaced with another blissfully thick cock. His second cock of the night slammed in without an ounce of ceremony and little resistance after Castiel’s ass had been fucked open, sloppy and ready. Castiel barely registered the sounds of his roommate moving around in the next room.

He could hear a muffled swear of Fucking Hell…again? Already? as guy number two started fucking into him. It was just as rough, selfish and greedy as the first guy. Castiel shoved back, clenching down and groaned in the most filthy, needy sounding voice that he could.

It seemed his second partner had decided he was going to top the first. Fingers dug viciously into Castiel’s hips and yanked him back into each powerful thrust. Castiel yanked at the sheets as pleasure burst inside of him. Every other thrust seemed angled to nail his prostate and Castiel couldn’t stop the tumble of sound pouring out of him.

Castiel was being loud enough to compete with the loud, banging slam of the headboard against the wall and the creaking of the mattress. Skin slapped against skin, his ass aching and burning, as his toes curled and his mouth fell open.

He couldn’t have formed a cohesive though if his life had depended on it and that was exactly what he’d needed.

The sounds of fucking echoed in his room and, without a doubt, through the suite and out into the hall. He ended up coming, completely untouched, with a loud keening wail that only seemed to drive the man inside his ass even more. Every single thrust after that had his sensitive body shuddering and hitching little sobs escaped into the air.

A second load was emptied into his ass before the soft cock slipped free.

“Hell of a fuck.” The praise washed over him as he collapsed onto the sheets, come and lube leaking out of his fucked open hole. He could only groan when fingers pushed into his used ass, finger fucking him, as he twitched and his cheeks flushed. A low, broken sounding whimper escaped as the fingers inside of him spread wide. “Look at that little ruined hole.”

“We wrecked that sweet ass.”

“You have any toys?”

Castiel managed a rough under the bed as fingers curled in his hair and yanked the same time fingers rubbed against his prostate. The sound of his toy chest being dragged out, opened and looked through didn’t even register as he moaned loudly at the stimulation.

The disappearance of the fingers did register. Castiel shuddered and looked over to see his biggest toy laid next to his face. He was turned, a cockcage locked onto his cock and a band around his balls, and then he was once more on his belly.

“Make sure you lube that ass.” A hand braced on his lower back and the end of his lube bottle was literally shoved into his ass before cold liquid poured into him causing him to jerk. “There we go.”

He clenched and squirmed at the feeling of cold, slick lube sliding deeper inside. The bottle disappeared shortly after and his toy was lifted to push into him. It burned and burned as the toy spread him wider and wider with each inch that sunk inside.

“Look at that greedily little hole.” the dildo fucked in deeper and deeper as Castiel shoved his face against the mattress with a cry. “He’s going to take the whole thing.”

Castiel’s ass clenched instinctively as they paused, the toy only half way inside, before rolling him over. Once again one of the men held his legs wide and the other leaned forward. He moaned, head shoved back, as the toy was fucked into him again and another few inches disappeared.

It only took a glance down to show how the horse cock sized dildo was splitting his ass. More and more pushed in, until he had taken the entire toy and a hand brushing against his stomach had them whistling.

“Holy shit. You can see it through his stomach.”

“The second I saw it I had to see this slut take the whole thing.”

Castiel whimpered as fingers stroked the toy through him and it was slowly pulled out, inch by agonizing inch, before being fucked back in.

In and out.

In and out.

The giant dildo fucked deep with each thrust and Castiel moaned louder and louder, body heating and face flushed, as they commented on what a good whore he was, how greedy his hole was to be filled and how they couldn’t wait to fuck right back into him.

By the time they were ready for another round Castiel was begging and begging for release but the cage trapping him wasn’t coming off and the toy was slowly slipping from him until his gaping hole was on display.

“You’re going to ride me, slut, and then Luke is going to bend you over the bed so he can pound that sweet ass of yours.”

Castiel’s legs were shaking by the time he was straddling the man laid out on the bed, sinking down onto his cock and whimpering at the need to come. “Please…please—”

“After we’re finished and only if you’ve earned it.”

Castiel immediately started rocking his hips, desperate and needy, as he fucked himself down on the cock impaling him. A hand smacked his ass causing him to jolt, a choked whine escaping, before he was moving faster and faster.

“That’s it. Show us how much you want to come.”

His legs worked as fast as he could, a hand braced on a firm chest, as the mattress started to groan lowly and the headboard knocked against the wall at an increasing tempo. In Dean’s bedroom, the same room that set right against his wall, he could hear Dean cursing loudly.

The sound of his roommate’s frustration had him moving faster and faster, moaning loudly, as a large hand continued to smack against him to urge him on.