Warning: Contains graphic content, adult sexual themes. Wincestiel. MalexMalexMale. Top!Sam, Middle!Dean, Bottom!Cas. Written for my friend, Evan. Don't like, don't read. I do not own Supernatural, its plot, or its characters.
How did it end up like this? How did it start? Dean couldn't help but to think back to the last night they were supposed to be alive. The apocalypse coming to a head finally, and the world was ending. They didn't know how, exactly, they just knew when. And he swore to his friend, his guardian angel, that he was not going to die a virgin. The attempt to take Cas to a strip club was a complete failure. So he needed to change tactics, and maybe pound back a few more drinks. When they returned to the hotel, that's when it happened. They happened.
And that was six months ago.
Dean never thought it would happen again, that it was a one time thing. But it wasn't. And it did. More than once they found themselves within the comfort of one another and a few too many beers in. Emotions started pouring out and sex was just the climax of a brewing storm. Which was why they were here now.
Dean's thoughts broke away when the angel above him whimpered and moaned, the back of his hand pressed against his mouth to try and silence the sounds. Dean hated it when Cas tried to muffle those beautiful noises, but he also loved the way he blushed around that hand. Dean stroked at the angel's cock after he pulled his mouth off of it, watching his friend wiggle and moan and slowly come undone. This is where they always found themselves, and surprisingly, after only a few months of this, with no prior experience, they were both getting pretty damn good at it.
But it was all about to fall apart when he heard the lock turn in the door. Dean had less than five seconds to pull his hand away from Cas and turn to sit on the edge of the bed, trying, and failing, to look as natural as possible with a disheveled angel behind him. Cas was left lying on the bed, panting and bright red from cheeks to shoulders. His coat, jacket, and button up were all opened and his tie was undone, lying over the front of his shoulders and disappearing below his layers. His pants were opened though Dean was kind enough to tuck him back into his briefs, though they did little to hide how hard and twitching he still was.
Sam opened the door, and Dean knew he knew. He didn't look inside yet and Sam could tell that the room smelled like sex. "Jesus, Dean, why didn't you text me to let me know that you brought a girl ba-" Sam froze, dropping the bag of convenient store goodies he had been carrying. He expected some blonde, halfway drunk and Dean halfway naked. But it wasn't a girl on the bed. It was Cas.
Sam looked at his brother, his brows pushing together in confusion. "Dean… What?" He didn't know what to say. Dean felt like an ant under a microscope immediately and stammered, "Sa-am… I… uh. I can explain." How could he possibly explain this? "So, this is the profound bond you two seem to share?" Sam bit out. He felt hurt, betrayed, that they would keep something like this from him.
"Sam, Dean do share a profound bond because of when I raised him from Hell. This is just an extension on that bond." Cas spoke up then, and Dean looked over at the angel and give him his best 'not helping' look. Sam ignored the angel simply because he didn't like what he just heard. "Jesus, Dean, you could have told me. I would have understood." Dean didn't seem so convinced, but there was something else in Sam's eyes. Something that he couldn't read as easily. "Could you, though?" The skeptical sound in his brother's voice hurt.
Sam got angry then, kicking the bag out of the way of his feet and slamming the door shut behind him. "Yeah, I could, Dean. Dammit, I love you. I always have. And it's not just because we're brother's either. It's more than that." Dean almost didn't notice how quickly the behemoth of his brother covered the distance between them until it was too late and Sam was grabbing his shirt. Pulling him to his feet, Dean closed his eyes and braced himself for another broken nose before he felt lips crash into his own. His eyes flew open and he could see Sam's face, brows sewn together and eyes closed tight as they kissed. It was crushing against his mouth, but Dean, slowly, fell into the feeling and let his eyes close again. The moment he relaxed is when they kiss eased and the two Winchester boys began working their lips together.
Cas sat up, ready to throw the two apart the moment a fight broke out, but it didn't happen. Now punches began to fly and blue eyes opened wide as he looked at the two boys, kissing one another. And Dean seemed to enjoy it. Eventually. He even groaned against Sam's lips. Immediately, Cas felt jealousy fill his chest before he was leaning in and kissing at the small of Dean's back, pushing his t-shirt up slowly. He needed the attention, too.
The kiss broke and Dean took the moment to grab his shirt and pull it up over his head, dropping it onto the floor and revealing his chest, and the tattoo that was upon it. He looked up at Sam in silence before leaning in and kissing his brother again, working his jacket off of his shoulders. Slowly stripping his baby brother's upper half. The moment the last garment fell to the floor, he pulled from his brother and turned to look down at Cas. The angel was so beautiful, his blue eyes looking up at him, especially the way he licked his lips. Dean pushed his layers off of his shoulders and let them pool on the edge of the bed while Cas started working open the front of his jeans.
Dean felt the button pop on his pants before the zipper was pulled down and his briefs and jeans were pushed down enough for his hard cock to spring free. He groaned, low in his chest as his cock gave a hard twitch before Cas leaned in and wrapped his lips around the lead, giving a slow suck. Cas was so much more eager now with Sam here. Maybe he was jealous, and Dean felt pretty damn close to a god with both men pining over his attention. He almost didn't notice Sam leaning in behind him, kissing along his neck slowly, down between his shoulder blades and back up again. Cas's mouth felt too good, sliding down slowly, taking more and more in with each motion, sucking just perfectly. God, when did an angel get so good at cock sucking?
Dean let his head fall back, leaning it against Sam's shoulder. He almost forgot how tall his brother was, but when they were this close, it was hard not to notice. Sam slid his hands up and down Dean's chest and sides, slowly feeling him relax under his touch. He watched over his brother's shoulders as Cas sucked him off, biting his lip and feeling his own cock harden in his jeans. He shifted uncomfortably before pressing against Dean's ass. He felt his brother stiffen slightly. "Sammy, I don't…" He felt Sam's teeth scrape over his skin and silence him. "C'mon, Dean, just once?" Dean knew full well that if he looked over his shoulder, he would see those green, watery puppy eyes looking back at him, and he knew he couldn't handle it. So he chose just not to say anything.
And Sam took that as an invitation.
That was the thing about Dean, his silence spoke volumes, and when he was all hot and bothered and panting, Sam knew he could get away with anything, at least once. Slowly, Sam hooked his fingers into Dean's briefs and pushed them down, along with his jeans, until they were completely off. He knelt behind his brother, guiding each leg up as he stripped him of his clothes. Without waiting for permission, Sam's hands slid up Dean's thighs slowly before gliding over his ass. He had to admit, Dean was pretty well off here. It was round and perfect, soft and muscled just right. He bit his lip at the groan that came from his brother as Cas sucked harder, bobbing his head a bit faster. Sam massaged his hands into Dean's ass before spreading him slowly and leaning in, slowly running his tongue over the puckered entrance. He felt his brother stiffen and moan wantonly from above him, and that only drove him on. Sam worked his tongue slowly against the tight hole before pushing in, licking and rolling his tongue against him.
After a few more minutes, Sam pulled back and sucked a pair of fingers into his mouth, getting them wet before pressing one against his brother's hole. He looked up at Dean waiting for a word that would make him stop, and when he didn't hear any, he pressed in to the first knuckle. Then the second. He knew Dean was uncomfortable by the way he tightened up around him.
But Cas was doing a damn good job at distracting him.
It didn't take long before Dean started to relax again and Sam was able to start pumping his finger, feeling each push in loosen his brother up more before he was able to press in a second finger. He spread them, slowly, scissoring them inside of Dean, feeling him stretch around his fingers, and hearing him groan. He knew that it had to be painful, but he also knew that it had to feel great paired with Cas sucking on his cock. Sam twisted his fingers around and curled them, brushing them over the bundle of nerves that was inside of his brother and sent Dean into a frenzy. Dean nearly screamed, yelling out and thrusting back against Sam's fingers, a bit of precome shooting down Cas's throat.
And Sam did it again, smiling at his brother's reactions each time his fingers brushed over those nerves.
"Ca-as… Sam… I'm… S-Stop…" Dean needed them to stop or else he was going to finish early. And the last thing he wanted was to be down for the count and leave his brother to deal with his angel. He might let Sam touch him all day, but there was no way he was going to touch Cas. He was going to have to find his own damn angel.
Cas pulled back slowly, and Dean watched as his cock popped out from those swollen lips, running his fingers through his hair slowly. He loved those eyes when Cas looked up at him. Sam, however, was a little more apprehensive when it came to easing off. He felt his brother's smile against his shoulder as he stood before his fingers curled again and he rubbed them hard against his prostate one last time, making Dean yell out. When the fingers left, he felt empty. And he didn't like it. Reaching down, he pulled Cas's pants off, along with his briefs and socks before he turned and kissed Sam hard. He pulled on his brother's shaggy hair, groaning against his lips and grinding his cock against the front of his brother's jeans.
He took his time to open up Sam's pants and tug them down, wanting them all naked as quickly as possible now. He was impatient and needly. When Sam's cock sprung free from his pants, Dean leaned in and kissed the head slowly, groaning before taking it into his mouth and sucking a few times, bobbing his head and watching his brother's reactions. Sam tipped his head back, his body flexing as he tried not to thrust into his brother's mouth. He had to admit, he liked the view, but even that didn't distract him from Cas, who was laying back on the bed again, his legs spread open and his hand wrapped around his own cock, stroking slowly, waiting for Dean.
Dean pulled back when he heard his angel whine. A grin on his face as Sam's cock popped lewdly out of his mouth before he turned, climbing on top of Cas and slapping his hand away from his own cock, taking both of the angel's wrists into his hand and pinning them above his head. He reached between them, stroking his own cock slowly before he held it as he pressed against Cas's entrance, slowly pushing in and feeling the muscles give in from the familiar feeling. He groaned, though this wasn't their first time, he was just as tight as he was when they started. Dean bit his lip, pushing in inch by inch until he was sheathed entirely inside of the angel.
He leaned down, kissing those sweet, swollen lips softly, waiting for Cas to relax completely. But something pressed against him. Dean pulled back, looking over his shoulder to see Sam kneeling behind him on the bed, the head of his cock pressed against his entrance. Sam was looking at him through his lashes, kissing his shoulder softly as he pressed a bit closer with each second that passed by. He was a lot bigger than his fingers, but still, the head of his brother's cock breached Dean's walls rather easily. The rest was a slow burn as Sam pushed slowly in. But at the same time, it made his own cock give a hard twitch. He throbbed inside of Cas, making the angel whimper and squirm.
Dean bit his lip hard, barely short of drawing blood, before Sam was finally fully inside of him. Dean rolled his own hips experimentally, and the mixed feeling of pain and pleasure, along with the moans that came from both men, was almost enough to make him come right there. That was when Sam moved, slowly pulling out before pushing back in. Each thrust shifting slightly as Sam searched for the perfect angle. Cas moaned and writhed beneath Dean. Sam's movements were pushing Dean's cock deeper and deeper inside of the angel until finally, Sam brushed over his prostate.
Dean groaned, dipping his head down against Cas's shoulder as he started to shallowly thrust in time with Sam. Each pull, Dean pushed, and with each push, Dean pulled. Sam, however, impatiently started to pick up the pace, gripping Dean's hips and thrusting harder into him, sending him deeper into Cas. Their moans ran together, each one panting for their own reasons. Dean grabbed Cas's hair, pulling him into a rough kiss to drown out the sounds. And Sam didn't like that one bit. He wanted to hear his brother, watch him come undone from his cock. He thrust in hard, slamming right into Dean's prostate and making him yell out against Cas's lips. Each thrust after that was harder, rougher, and spot on.
Dean held on to Cas, panting hard as his shallow thrusts were driving in deeper and deeper into Cas, sending long, drawn out strokes over the angel's prostate rather than the rough, spot on ones against his own. "S-Sam… Slow down… Or I… Fuck, Sammy…" Dean groaned against Cas's shoulder, reaching down between them. He needed Cas to finish first, he couldn't leave his poor angel unsatisfied. Wrapping his hand around Cas's cock, he started stroking him, in time with Sam's thrusts rather than his own.
It didn't take long before Cas was tightening down around his cock and yelling out. His muscles were throbbing against Dean's cock, milking him for his own come as the angel shot the sticky, white load across his own chest and Dean's hand. Dean was soon after, the tightness on his cock was too much paired with Sam's relentless pounding inside of him. He groaned, biting down on Cas's shoulder, marking him as he came, hot and heavy inside of the angel.
Sam, though. Sam wasn't finished yet. He growled at the two spent boys and grabbed Dean's hips, holding them so he couldn't pull out of Cas just yet, and slammed in hard. His sack slapping against Dean with each thrust, filling the air with the needy, frantic moans of Cas and Dean. They were sensitive from their orgasms, and Dean was so tight. Throbbing and hot like a vice around Sam's cock as he hammered inside of his brother before he slammed in and deep as he could and came against Dean's prostate, his cock throbbing hard with each spurt of come. Dean whined and groaned as a few more spurts shot from his spent cock inside of Cas because of Sam.
When Sam finished, he nearly collapsed upon both of them, rolling off at the last second and sliding out of his brother. He groaned and relaxed back on the bed, his forearm across his eyes. Dean slowly pulled out of Cas and took his time to grab a dirty towel from the floor and clean the angel up. His legs were shaking as he slowly dropped the down and pulled the covers over the three of them. Laying down on the bed between his angel and his brother. There were no words any of them could say. Some things were better left unspoken for now.