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When Dean thinks about it now, it makes him feel kinda shocked that he never questioned about the righteousness of his actions back when Sam was a teenager, not really. Sure he knew that what they were doing was wrong, but he can't bring himself to regret anything. Sam had been fifteen when it started. Kisses, hand-jobs, occasional blowjobs. Not much talking, not analyzing the reasons or consequences, simply because there just wasn't any need for any of that. Back then they both needed comfort only the other could provide, so really, he can't regret something that made them both just forget about the rest of the world for during those stolen moments in the dark.
As time went by, their 'experiments' went a little further, and then even more further until one night Dean found himself buried deep inside his little brother, Sam writhing under him, arching his back and sinking his teeth on Dean's shoulder.
Dean doesn't regret that either. It only seemed like a natural next step.
It only changed when Sam got accepted to Stanford and left. Well, not even then because no matter how sad or even disappointed Dean was, wasn't that what he had always wanted for Sam; a better life. A normal life. But when Sam came back...
Dean knew the only reason Sam left Stanford and came back to Dean was the fact that Jess was dead. And somehow for the first time ever it made Dean feel like a scumbag, like he should have known. You're not born a Winchester with a chance to live a normal life. In fact, sometimes Dean feels like he's the one responsible for Jess' death and putting Sam through so much pain.
During the first days on the road after Sam comes back, he's quiet. Too quiet, and Dean has no idea how to break that silence because he honestly doesn't know what to say. Sam blames himself, Dean blames himself, and his feelings are torn in two.
When they stop for the night, book a motel room and settle in, Sam just lays on the bed, unmoving, staring at the ceiling with empty eyes, and Dean's heart aches. He can't stop wondering if everything would have turned out differently if only he had left Sam alone all those years back, refused his brother's needs, because a small insane voice inside his head keeps whispering to him that it was Dean who tainted his little brother and maybe, just maybe Sam could have had normal life if Dean hadn't been too weak to resist Sam. Maybe it was Dean who with his sins ruined Sam's life. Doesn't matter that it was Sam who started it.
He knows his thoughts are inconsistent and incoherent but he just can't help it.
Sam seems to shut the outside world out again, and the only thing Dean can do is give him time. Dean has seen all this before; back when they were young. Back when Sam was broken and incomplete, and he should see it coming, but he doesn't.
It's been six days since they left Kansas. The motel room is different this time, it's past midnight, and Dean is relieved because finally Sam seems like he's sleeping after six sleepless night. Turns out Sam is not asleep, just quiet like he's been for days. Dean doesn't even hear Sam crossing the small place between their beds, but then Sam's there, and Dean can see his silent figure in the dark next to Dean's bed. And then Sam is really there before Dean has any time to process the fact that Sam's next to him, not by the bed, but in the bed. And Dean's emotions go haywire.
“Sam...” he whispers, a hint of desperation coloring his voice. They used to do this, to comfort each other, but this time the comfort Sam is looking is for the wrong reasons. “Sammy...” Dean tries again but Sam doesn't listen. He sheds his boxers and t-shirt, and Dean closes his eyes.
Sam's body feels totally different than it used to; taller, sinew, and just... different. But it's still Sam, and although Dean's mind is full of contradictions and protests, one thing hasn't changed over the years. Dean still can't refuse his brother. Wrong reasons or not, Sam is hurt. Broken. Torn. And if this is the comfort Sam needs now, Dean can't deny that from him. Especially when he has missed Sam during all those years like his brother was some kind of amputated limb; gone, but the phantom ache has remained.
“Come on then...” Dean says quietly and pulls Sam close, under the covers. “It's okay...” he whispers, burying his nose in the soft hair of his brother. “You're gonna be okay. I got you.”
“I know”, Sam just whispers, and all Dean can think of is how good it feels to have his baby brother back in his arms, no matter what kind of fucked up situation led them back to this. But the contradictions are gone. Sam needs him, and like it has always been, there's nothing Dean wouldn't do for Sam.