Wayfaring Stranger
When he can't sleep, he wanders. Aimlessly, recklessly. Wherever his feet will take him. Dean doesn't know about this. He would probably start spouting off all this bullshit, like how he shouldn't be alone or what if something happens? But he can't help it.
When he can't sleep, his feet ache. His legs itch and his thighs shake. And he knows he can't sit still, can't lay still, can't not move no matter how hard he tries. So he quietly slips out of bed, steps into his jeans, grabs his coat while rummaging in the deep pockets to make sure his cell is there—just in case—and glides out the door. All those years of hunting have paid off in one regard; at least he's able to sneak around undetected.
When he can't sleep, the world seems way too big. He feels way too small. Insignificant, even. But then again, at 3am in the middle of the country, on back roads surrounded by fields of tall grass, everything seems empty and deserted. That's how he likes it, though. He likes feeling alone, as if he's the only person left on this shell of a planet. Because when you get down to it, he pretty much is.
When he can't sleep, his feet tap a beat that begins a long melodious chain of events in his mind as he walks. Tap tap tap. Mom is gone. Tap tap tap. Jess is gone. Tap tap tap. Dad is gone. Tap tap tap. All long gone. Too far gone. Gone gone gone.
When he can't sleep, he thinks about running. Far, far away. Not looking back, not even for Dean. There's too much coming, too much underway that he isn't sure he'll be able to handle it. Sometimes he can feel the evil stewing in his heart, waiting for the chance to surface and take hold of his life.
When he can't sleep, he hates himself. (But then again, he hates himself even when he can.)