Dean

When you and Dean cuddle you can almost never find the perfect cuddling position. Every single night it changes from one position to another. You sometimes fall asleep cuddling on the couch and wake up cuddling on the floor.

Sam

Sam will cuddle with you in the car. If he sees that you are falling asleep in the back of the Impala while on one of your many road trips he will get Dean to pull over so you can snuggle into his side as you fall asleep.

Cas

When you cuddle with Cas he will pop in and let you lay your head on his chest until you fall asleep. Since he is an angel he doesn't sleep so he will either admire your beauty while you sleep or if he has some angel buisness to attend to, he will pop away for a bit, but he will always pop back before you wake up the next morning.