Spoilers for season five!!!!
Disclaimer: Supernatural and certain characters belong to Eric Kripke and Warner Brothers. No profit is gained from this writing, only, hopefully, enjoyment.
In this place, he says yes.
He and Sam and Adam are in the Beautiful Room, and Zach's sending up the Angel Signal, and Dean says yes in his head. He looks at Adam bleeding on the floor, the guy naive enough to think he'd get out of this with something, much less something he'd actually wanted. Poor kid. There's no way out, and sure as hell nothing coming with but more pain and shame. Knowing Zachariah, Adam never would've seen his mom again, probably wouldn't've made it up to Heaven in the first place. Zach's not one for keeping his word or doing the right thing.
The Room is shaking and all of them with it. Dean doesn't bother steadying himself, just rocks with the force. There's a sound rising, and he knows what it is, recognizes it from the times with Cas. Soon the force of angelic voices will break and shatter everything in the room, from the obvious glass to the more hard to believe ear drums. Sam and Adam will bleed even more than they already are in just a minute.
Sam. Dean glances over at him again, lying there on the floor in the wreckage of Beautiful Objects. He quickly looks away, but not another five seconds pass before he's back to staring. Decades with this kid, years and years and more time spent with him than anyone else on the planet. He gave Sam baths when he was a bratty-ass toddler, and let him eat all the good food, and he put Sam to bed and told him bedtime stories about the most boring things imaginable. He knows almost every single facial expression and every single habit.
He loves Sam. . . more than anything. Anything. He gave up his future once to bring that kid back.
He'll do it again.
Glass starts breaking, and Dean watches Adam curl tighter into himself. He watches Sam, too, and Sammy. . . Sammy watches Dean right back. He watches Dean as blood starts slowly rolling from out of his nose, down over his mouth and chin. He watches with slit eyes and his hands to his ears when the sound of Michael's arrival grows deafening. Literally. Sam watches Dean, and Dean. . . Dean watches Sam right back.
He watches; he stares. He glances at Adam one more time and then never takes his eyes off Sammy.
Dean says yes. As the shaking gets worse, as the ceiling of the Room splits, as Sam bleeds and moans in agony, Dean says yes with every fiber of his being. Sam is here right now, and because Dean is saying yes the kid always will be. He'll be Sammy, and he won't say yes.
Dean's the oldest. It should be him going first, anyway. Mom, Dad, and then Dean. It only makes sense.
It's only the right thing to do.
"Welcome, brother!" Zachariah suddenly shouts, and it's Sammy's eyes moving over to the angel that comprises Dean's last sight.
Everything goes white, and Dean screams "Yes!"
And Michael agrees with him.
Sub-Echo In Never Will