Turns out the dogs only come when you're running. When you choose to honor the deal you made, apparently, when you don't try to get something for nothing - then your flesh stays intact, isn't ripped to ribbons by slavering jaws, and your throat stays in one piece.
He doesn't think he's early - took the gift of the leap year's extra day and figured it in - and he'll never forget the date and time it finally clicked, when he realized how simple it would be to bring Sam back.
Be pretty funny if the reason he's at a crossroads all by his lonesome is that she's out with the pack, searching for him, ready to tear him down and snap up his soul. Maybe not funny, exactly. Sam sure wouldn't laugh, even if he threw in a line about delusions of classical grandeur.
But that's the point, isn't it? That Sam's alive, free to be as unamused as he likes, able to live and make the world a place worth saving just by being in it. Sam calls him a hero sometimes, sometimes even without a smile behind it, but it's Sam who's been brave, put his big brain to use, and figured out a way to keep all the other hunters and stragglers under his command, showed them how to win against crazy odds.
Sammy'll be alright.
Dean's never liked waiting, and every moment the demon delays is another moment Sam can use to track him down. Bitch needs to hurry up, before Sam comes running up with something that will invalidate the whole thing. And Dean's had a year to get used to the idea, a year of living hard and bright, knowing he's doing the right thing, and counting on that one sweet moment of rest before his soul heads for hell.
Maybe the demons won't start with the torment right away. Not that he expects them to be merciful - he's not an idiot, despite the way he comes across, but then who would look good standing next to genius Sammy? This year could certainly have been a lot worse. Sam could have gotten sick, he could have gotten sick, something. A year is just enough time - long enough for him to do what needs to be done, long enough to make Sam feel like he did his best, too short to trap Sam into staying with him instead of going back to the wonderful life he knew without Dean. Ten years is a lifetime, and it wouldn't have been fair to bind Sam to him for so long. A year is just right.
And Sam likes deadlines, likes knowing that things have boundaries, reasonable edges. He's told Sam in no uncertain terms not to keep looking for answers after the year is up, and though Sam's always had issues with following orders, in this case it matches his natural inclination. Little straight-A Sammy will wipe his brain clean like he did once before and go back to a place where he felt safe and secure. And Dean knows he helped make it that way, putting a bullet in that yellow-eyed sonovabitch, stopping that mouth that kept insisting on how special Sam was, when all Sam wanted was to blend, be one of the crowd.
Sam can do that now; no one's holding him back anymore.
When he sees her in front of him, he remembers everything from the last time they'd met and the time before that, when her brother came for him. "Dean," she says, sweet voice low in the darkness, and he meets her big dark eyes and smiles. "I knew you'd like me like this," she says, grinning back at him. "It's no secret that you click with kids."
He's touched, actually, that she tried for a shape he'd like and not just respond to physically. "You're the cutest Reaper I've ever seen," he says.
She beams up at him and shakes back her tangled black curls. "You're my favorite," she says confidingly, winding small, warm arms around his neck when he crouches to hear her better. She locks her legs around his waist as he stands back up, leans her head against his chest and plays with his amulet.
He can hear the hellhounds' bloodthirsty growls and their bitch-mistress's demented cries getting closer, but she pays them no heed, just snuggles into him more securely. He can feel his heartbeat pounding against the softness of her cheek. "Can we go now, Dean?" she asks, like he's promised her a wonderful treat. She looks up at him with complete trust.
"Sure thing, darlin'," he says, and feels her hand come up to cup his face, loving as a mother's gaze, steady as his girl's ride. He closes his eyes and lets go.