Dean-
You steal his leather jacket when you know that he's going to be gone for a fews days. He normally let's you keep it as along as he gets something in return, like, say, one of your hair ties or your bracelets.
Sam-
You steal one of his flannels. Yes, its cheesy and corny but you can't help but in love with how big and warm they are. It doesn't help that you are totally in love with his scent and those things always smell like him.
Cas-
You wanted to do something to spice up your relationship, so what do you do? You take the man's tie one night and wear ir before Mr. Hot Wings isn't an awkward virgin anymore.
Gabriel-
Everyone knows how much Gabe loves candy, so one day you decided to buy him some boxers with little hersey kisses all over them. He fell in love them by the way. One day you had to do laundry and all of your neans were dirty, so you grabbed those bixers and wore them all day. Up until Gabe found you digging theclothes out of the bottom of the washing machine with his boxers on you.
Lucifer-
Luci's vessel has an old army jacket that you just lo e to wear and cuddle in. He doesn't understand why, and you just think its comfortable. He isn't complaining though, its still a very sexy sight for him.
Crowley-
You love wearing Crowley's white shirt. You think they're comfortable, you don't have to wear a bra underneath them and he doesn't care if you eat food and stain the shirt. Hey, no bra and food? That's a good deal.
Adam-
You needed to wash some blood off of your favorite jeans one day, and it was also laundry day at the bunker so you had practically no pants. That was until you went into yours and Adam's room and took a pair of his workout shorts. While you were washing your pants, Adam snuck up behind you, kissed your neck and whispered in your ear, "Its about time you got in my pants. I've been getting yours for months now."