Dean - You'll curl up against hm, fist on his chest as he holds you. He'll always give you a small kiss on the forehead while you doze off, which makes you smile.
Sam - Sam's like a giant body pillow. The most muscular pillow you'd ever slept on, buts it's surprisingly comfortable. You'll nestle your head by his chin, arms curling under his armpits while he strokes your hair. You can sleep easy under his touch.
Castiel - He doesn't sleep with you, but during his time as a human he did. He was a restless fucker, constantly shifting about before he was practically draped over you. You'd sleep on your stomach while he curled his legs around one of yours, and arm over your back. Sometimes he'd hold your hand in his sleep, which made you smile.
Jack - Like said, he doesn't sleep much. He never misses the opportunity to watch you rest though. It fascinates him - the human need for sleep. Sometimes he'll whisper for a few minutes at a time to see if you're awake, if not he'll just run his fingers over your arm in a pattern while admiring your calm expression.
Charlie - Charlie loves to snuggle into you, hands caressing your shoulder blade soothingly as you rest your arm over her shoulder.
Meg - She hates admitting it, but she likes watching you sleep, your subtle expressions as you dreaming...She'll whisper sweet words into your ear and caress your upper arm as you rest.
Garth - You two catch pick some position to sleep in. You both move around in your sleep, so it's really whatever is comfortable at first and won't leave you strangled in the morning.
Gabriel - You like to tease him as first since he doesn't sleep, but you need to. You'll act like you want him before turning around and cuddling back into him. He will moan about it was a few minutes before giving in and cuddling you instead as you spoon.
Balthazar - He likes to admire your beauty while you rest. He can do it without being called a creep that way.
Benny - Benny rarely sleeps, but when he does, he likes to hold your hand and face each other. He's afraid if he spoons you he might lose control when he wakes up and bite you.
Lucifer - Despite his status of evil, he's a gentle cuddler. He knows your fragile. He'll even hold your hand to cool you down when it's a warm night.
Chuck - Sometimes you don't even make it to the bedroom when it comes to sleep. You'll end up crashing on the couch after hours of writing and rewriting, him resting on you. His head will be on your shoulder, arm around your middle as you pet him lazily, calf partially draped over his thighs.