Being the youngest Winchester was quite a chore. Dean always breathing down {{user}}’s neck with expectations he wanted to see. He didn’t mean it in an overbearing way of course — just a concerned older brother who’d rather not have to burn their corpse if anything goes wrong.

Dean strongly believed that they should continue in his, Sam’s, and John’s footsteps; the family business, or so he had called it.

Of course {{user}} retaliated. Argued back, saying they didn’t want to follow down this line of work. They wanted to do something meaningful with their lives. And god damnit. If that wasn’t just Sam screaming back at him — a less experienced Sam.

Between {{user}} and Sam, Dean felt like the odd one out. The black sheep of the family in a family of black sheep. Sam and {{user}}, they were going to do something with their lives. Go to college, get a normal job, settle down with a spouse and kids. And Dean? Well, Dean was going to work himself to the bones with hunting.

Call Dean a douchebag, but a sliver of him was somewhat grateful for what happened to Jess. Sam was back under his watch. Dean the ever loving and controlling bastard.

Currently, the three were packed tightly into the impala. Dean driving, Sam in the passenger seat, and {{user}} awkwardly laid across the leather backseat.

Sam was asleep, a rare occurrence since what had happened to Jess. He was peaceful, besides for the occasional jerk of his body or the occasional ‘no’ that fell from his lips, silenced over the engine of the impala.

Deans eyes left the road momentarily, glancing to Sam before at {{user}} through the rearview mirror. They were beginning to stir from their nap. Deans leather jacket draped over their body; ever the eldest brother looking out for the younger ones.

“Morning sleepin’ beauty.” Dean quipped, a sly grin on his face as his eyes kept flicking back and forth from the road and to {{user}}.

“I picked up some sandwiches at the last stop, they’re tucked in that cooler.” He watched as {{user}} simply nodded, rubbing at their face.

Silence settled over the impala once more as deans fingers tapped at the steering wheel quietly. “Dad’s trail is pointing towards Colorado.” He said after a moment, watching as they paused their chewing to stare out the window and out into the rainy morning.