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It’s one of his friends who tells him about it for the first time. 

They’ve been working together at the garage for a few weeks now, and Tom is the kind of guy who talks about everything, even the things you wish he didn’t, and quickly, Dean is aware of all of his friend's sexual behavior. 

But then his girlfriend dumps him, and that’s when Tom tells him about his “ability”. 

“What?” Dean says, his eyes wide open as he tries to understand what his friend just said. 

“I bend over, put my legs behind my head, and I suck my dick” Tom replies, “Honestly? It’s even better than when someone else is doing it. You should try”

So, Dean tries, as soon as he’s alone in the motel room. He starts by bending over as far as he can, but he can barely touch his toes.

He’s not one to give up so easily, so he tries again. And again.

He’s not even sure he wants to do it.  The idea of having his own cock in his mouth is disgusting. But he saw pictures of people doing it, and that’s all he can think about now.

The realization hits him one night while he’s cleaning his gun on his bed, trying to focus as hard as he can, even though it’s nearly impossible with the way Sam is breathing so loudly.

“Sam!” He finally snaps, “I swear, I’m gonna-“

He stops immediately when he sees what Sam is doing. His brother is still in high school, and in order to make new friends, he decides to join the football team. Dean thought it was a waste of time, spending all his free time practicing when he knows they won’t be here for the big game. But Sam is Sam, and he didn’t listen to him.

Dean is so glad he didn’t.

From where he is, he can see perfectly the way Sam bends over slowly, his tight red shorts making his ass looks even more perfect than usual as he reaches his toes without any problem, taking a deep breath as he does so.

Dean wonders if Sam could do it. If, maybe, he could put his beautiful and long legs behind his head and wrap those pretty lips around his dick.

“Since when are you so flexible?” Dean asks, pushing the gun away

“Since always?” Sam gives him his best bitch face, but Dean ignores him, too focused on the way his brother looks at him through his spread legs.

Sam continues his exercises, while Dean stays focused on him, the way his body moves, so gracefully, so easily.

Sam always looked like a doll, with his long silky hair, his never-ending legs, his perfect smile, his dimples, the way his nose twists when he’s concentrating. And his eyes, God his eyes. His multicolor eyes, holding all the stars of the universe in them. Shining and sparking like they’re made of glass.

The way he can do everything he wants with his body, twisting it in every position without breaking.“Dude, stop staring, it’s creepy” Sam says, taking Dean out of his thoughts

He licks his lips, knowing that his last words will be decisive. He shouldn’t ask for it, shouldn’t even think about it, but he can’t help it.

“Do you think you could put your legs behind your head?”

“What?” Sam frowns, stopping his exercise.

“Your legs, can you put them behind your head?”

Sam doesn’t talk right away, and Dean is pretty sure he just fucked up their relationship. There’s no way Sam knows what he wants him to do.  But then again there was no way for Sam to know that Dean wanted some red shoes for his birthday, and he still did.

“Nevermind, forget it” Dean says, taking his gun back into his hands. He would have gone out if it wasn’t for the major boner he has right now.

“I can do it” Sam finally says

“Are you sure?”

Sam nods before sitting on the floor, his ankles in his hands as he starts to lift his legs, and Dean wonders if he can hear how strong his heart is beating, like it could burst at any moment.

His legs are around his head while he smiles proudly at Dean, happy to have realized his brother’s wish.

“See? I told you I could!”

“Can you… Can you touch your ass with your nose?”

“What would I do that?” Sam frowns again, but this time, he looks at Dean like he lost his mind

“I don’t know, it could be funny”

“Yeah, ok” Sam says slowly, not really sure if his brother is testing him or if he’s really serious about it.

When his nose finally reaches his ass, his arms holding all of his body in the correct position, Dean feels his underwear getting wet. He’s breathing hard, his mind completely dizzy as he sees his brother's face so close to his own ass, so close to his dick, and it’s now or never, fuck the consequences. He’s gonna ask Sam to do it, he needs to, and maybe -

“You want me to suck my dick, don’t you?”

For a few seconds, Dean is sure he imagined all of it. There’s no way Sam, his innocent and naïve Sam, would ever think about something so dirty. He closes his eyes, trying to wake himself up from whatever dream he’s having, but when he opens them again, Sam is still there, on the floor, but this time, his shorts are gone, leaving him completely naked, his big and hard dick resting on his stomach.

“Shit, that’s not what you wanted” He says, a horrific expression appearing on his face. He covers his dick and bends over to put his pants back on, but Dean is quicker.

“No, do it. Please do it” He doesn’t care how needy he sounds, he wants Sam to do it. They’ll deal with the consequences later.

“Ok, I- yeah, ok”

“On the bed. Sit on the bed”

Sam nods and does as he is told, sitting right in front of Dean before pushing his legs up, giving Dean a perfect view on his ass. He’s even more beautiful naked, how is it fair?

He starts by licking the head of his dick, like a kitten, and Dean finally takes his dick out of his pants, holding it firmly in his hands.

“Have you ever done that before?” He asks

“No” Sam’s voice is shaking with desire and fear, but Dean smiles at him, encouraging him.

“Good”

Sam smiles back before starting to work on his cock again, taking more of it until he starts to gag. He can’t believe this, can’t believe what Sam is doing, for no one but him.

He strokes himself faster, trying to follow Sam movements, and slowly, he watches as his brother takes his entire cock in his mouth without gagging, his nose resting under his balls.

Sam is moaning as loud as he can, his eyes alternating between being close and being focused on Dean. Dean would be lying if he said that it’s not making him even harder.

They both come hard, Sam gagging and spitting on the sheets before unbending his body back into normal.

Dean is too far gone to do anything but watch, as his mind trying to cope with what is without a doubt the best orgasm of his life.

“Fuck” He says, panting hard, “Are you ok?”

“My back hurts a little” Sam admits, taking a sip from the beer next to Dean’s bed

“I bet it does” Dean laughs, pulling his brother in his arms, not carrying about the mess they made on the bed “Want me to massage it for you?”

“That’s the least you can do”

“Bossy bitch” Dean mumbles

“Jerk”

Dean smiles before giving Sam a sweet and innocent kiss. The total opposite of what they've just done.

“Thank you” He whispers, kissing his nose just to see it twist.

“You’re very welcome. Maybe next time I could suck yours?”

Dean will have to thank Tom as soon as he sees him