“Dare.” Castiel didn’t blink as he met Benny’s gaze with a challenge. He wasn’t chicken and it was ridiculous of the football player to insinuate it. His challenge was met with a raised eyebrow and a blank face that slowly morphed into something wicked.
Around him everyone else is staring but Castiel didn’t care. There were few things he wasn’t willing to do and he knew Benny well enough that he wasn’t worried.
So far there had been rimming, making-out, a blowjob, some toys and a shocking amount of truths of his classmates’ sex lives he’d never expected to hear. “You're going to regret that one, Cas.” Lucifer was smirking at him from the left but Castiel shrugged. He’d been the recipient of the rimming job and Victor very clearly knew exactly what he was doing. Castiel was hard pressed to think of a better rim-job from any one he’d fucked or been fucked by and it had him mentally humming in satisfaction.
“There is very little that bothers me.” He didn’t advertise his sexual experiences but Castiel wasn’t averse to trying new things or even old ones. It didn’t matter if it was male or female either. A warm body was a warm body and Castiel dearly loved pleasure since he figured out how to get it.
Benny grinned and leaned forward meeting his eyes with intent clearly in them, “I dare you to get Winchester off without touching his dick. Right here. In front of everyone.” He waved towards the area they’re in, the living room of Benny’s parents’ house and Castiel shrugged. It’s where almost all of the other dares had taken place and he’d been bent over the table getting rimmed only fifteen minutes ago. This was a piece of cake.
“No problem.” Castiel rose to his feet and glanced over at their school’s star baseball player who was staring at him with wide green eyes and something nervous in his expression. Idly he wondered if Dean had ever even thought about touching his own ass but figured considering the number of females he went out with that possibility was slim to none. Dean was pretty fucking straight and from what Castiel had heard he’d gone through the majority of the cheerleaders. “You ok, Winchester?”
“Fine.” Dean’s jaw clenched briefly, the muscle flexing, as Castiel thought about what he wanted to do. He was torn between fingering and rimming. There were multiple things he could do to get someone to come untouched and if Dean was sensitive enough it wouldn’t take too much.
“Lube?” the bottle in the center of the coffee table was tossed to him and Castiel turned to the dare at hand. He set the bottle down nearby and stepped right into Dean’s space, guiding him up and pressing close. It would work better if Dean wasn’t wound so fucking tight.
Castiel pressed their lips together and set about coaxing Dean into kissing him while his hands moved. He let them move down to settle on Dean’s ass, noting how firm it felt in his hands, as he gripped Dean and pressed them closer. Dean had a surprisingly plump ass and Castiel gave it another tight squeeze.
He eventually moved his mouth from Dean’s and trailed down, sucked lightly on Dean’s neck, while teasing the waistline of Dean’s pants with his hands. It was far better to loosen Dean up and when he felt Dean slowly responding he pulled away to start working Dean’s pants down.
Under his hands Dean tensed, shifting restlessly, as the others around them murmured and watched. He grinned when he heard a low moan that Dean tried to repress and it was easy to guide Dean over the edge of the couch once he’d waved people away. Dean’s pants and underwear rested down around his ankles exposing an ass that honestly should get fucked often but Castiel doubted that would happen.
It was a pity.
That’s an ass no one would forget he thought with a mental leer, grabbing the lube and squirting some out. He braced a hand on Dean’s back and rubbed over the puckered hole, slicking it up and slowly starting to work a finger inside. Dean was tight and tense but Castiel knew how to loosen a hole and he wasn’t about to fail a simple dare in front of everyone. He made sure to listen in case Dean wanted him to stop.
“Not going to work.” Dean’s voice was lower, rough sounding, and Castiel rolled his eyes. As if he’d ever failed at getting anyone he wanted to get off to come when he set his mind to it. Dean wouldn’t be any different.
“Trust me…I’ll have you moaning in a few minutes. I’ve never had a complaint yet.”
There was a chuckle from the other side of the room but Castiel focused on the task at hand. He rubbed the skin of Dean’s back, moved his hand to Dean’s thigh after awhile, as he focused on pressing a finger inside. It was hard to get Dean to relax but Castiel knew what he was doing and once he got a finger inside he immediately sought out Dean’s prostate.
“Fuck.” The word came out startled and Castiel smirked, eyes flicking up to meet Benny’s with a challenge. Clearly someone had never stimulated their prostate. Easy dare he mouthed and started focusing on that one point. Dean’s hole clenched around him and the body before him was shuddering as Dean struggled not to moan.
“Cheater.” Dean groaned it as he gripped the couch but Castiel sighed as he focused and dragging Dean’s orgasm out of him with only his fingers.
“Didn’t touch your dick; I’m completely within the rules. Not my fault you’ve never had someone touch your prostate before.”
There was a hiss when Castiel started a second finger in, fucking them in and out while occasionally brushing Dean’s prostate to pull out more of those bitten off sounds. He listened to the gasps and barely held back sounds that were escaping Dean the longer he teased him to the edge.
“I think Novak might have magic fingers.”
He had magic everything.
Dean’s moans got louder, his hole clenching repeatedly around his fingers, the longer Castiel drew it out. He had three fingers in while Dean gasped his name out and it was impossible not to get turned on by the sounds and sight of his fingers disappearing into such a tempting ass. His cock started to press against his pants and soon Castiel’s cock was aching with the need to fuck.
He imagined his cock replacing his fingers and the way Dean would moan his name while he fucked him right there in front of everyone.
“Fuck…please.” Dean’s breathing hitched and Castiel glanced at the room to see everyone watching, several looked just as aroused as he felt and Castiel felt smug knowing he was the one causing Dean to come undone.
Castiel pulled his fingers out, listened to Dean’s sound of protest and fished out his wallet to grab a condom. He wasted little time freeing himself and getting the condom out. A few strokes at him slicked up and he pressed against Dean’s hole. Fucking was very clearly not against the rules and at this point he was more than sure he could fuck an orgasm right out of Dean Winchester. He was practically panting for a good fucking.
“Do you want my cock, Winchester? Want me to fuck this virgin ass of yours until you come? Do you want to get off?”
There was another curse and Dean turned around. His eyes were wild and his freckled cheeks were flushed as the desperation of being on the edge got the best of him. Dean heard the challenge in his tone, caught the way Castiel taunted him with a quirk of his lips and just as Castiel knew he would Dean rose to the bait. Loudly. “Yes you asshole!”
There was little point in wasting time. Castiel started pressing inside, marveling at how Dean squeezed his cock, until he had bottomed out with a groan of pleasure. His eyes hooded and he waited for Dean to get used to the feeling of a cock inside him. It wasn’t smart to immediately start slamming into a virgin, at least a virgin when it came to getting his ass fucked, and Castiel wasn’t going to hurt his classmate over a dare or getting off to an audience.
He started off slow with lazy thrusts. It took a change in angle for him to hit Dean’s prostate and Castiel made sure he hit it as much as possible dragging out increasingly louder moans. Castiel knew Dean was on the edge, knew how close he was from being fingered and it shouldn’t take much to send him right over the edge securing Castiel’s completion of the bet.
The slap of skin against skin filled the room as Dean moaned and gasped, “Oh oh ooooh—there please yes there please come on…fuck!”
“Got to get him off without touching his dick. Put more effort into it.” Victor was smirking at him and Castiel resisted the urge to move one of his hands from Dean’s hips to flip the other football player off. “Plow that tight ass. Winchester clearly needed a good dicking.”
He was getting closer and closer the longer he fucked into Dean, snapping his hips forward quicker as he chased his own orgasm. Castiel could feel how close he was when Dean’s ass clenched down tightly on him and something like a wail escaped into the room.
His own release was quick to follow as Dean panted and shuddered under him, going limp under him, as most of the room applauded his success. “Good show, Novak.” His teammates were grinning at him as he pulled out of Dean.
“Hell of a show.” Came the agreement, “Hopefully it won’t mess with Winchester’s game.” The grin was more than obvious as Castiel dealt with his condom and clean up. “Though he’ll be walking funny after that.”
Dean finally moved off the arm of the couch, dragged his pants up with a hiss and slowly moved over to his spot. “How was it?” Benny smirked at him and Dean muttered something, glancing over at Castiel as he dropped down into his spot. There was a clear embarrassed flush to Dean’s cheeks and he wouldn’t meet anyone’s eyes, twitching and shifting in place as he winced. Castiel remembered the first time he’d been fucked and knew Dean would be feeling that for awhile.
The prep job could have probably been better but he’d been on a mission and a dare was a dare. It wasn’t like he was trying to get a second shot at Dean’s ass or anything. What was a little pain in the grand scheme of a dare?
Pleasure from his own orgasm had him grinning at the sated feeling. That dare had really turned out in his favor. He felt relaxed and loose. “Michael…truth or dare?” Castiel didn’t dwell on it and Castiel could see the grateful look Dean threw him. It was probably a little discerning for someone considered straight to get off on being fucked by another guy in front of so many of his fellow jocks. No doubt Dean would be hearing about moaning like a whore for weeks to come.
Castiel shoved it aside and grinned in a predatory way at Michael as he chose dare.