December 1995
The first time they kiss, it’s a comfort thing. It’s late and cold when they’re driving through Nebraska, and Sam watches Dean shiver on the edge of sleep for nearly an hour before he climbs into the backseat to sleep with Sam.
Dean sleeps the best when he’s in the car. He’ll stretch out in the backseat with Sam spooned against his front so they’ll both fit, and puffs happily against Sam’s neck under the big blanket that they share. He’s usually asleep within minutes, breathing right into Sam’s ear. It settles Sam easily, and his eyes droop. He can sleep anywhere really, but he sleeps the best with Dean next to him.