Dean
You sleep with your back against his chest and he wraps one arm around your waist while his head rests on his other arm.

Sam
You sleep facing his chest. He wraps you in his embrace and pulls you as close as he can without suffocating you.

Castiel
He doesn't really need to sleep. He will lay in bed with you though. You'll both lay apart facing each other. He is the first and last thing you see.

Gabriel
You two aren't a fan of sleeping close. You'll each sleep on your respective sides of the bed, but once in a while you'll wake up to a sweet surprise and be in his arms in the mornings.

Lucifer
Your head will rest on his chest while he wraps an arm around your shoulder. Your legs are intertwined.

Crowley
Your face hides in the crook of his neck and you wrap an arm around his chest while your legs become tangled.