The first time Dean caught a glimpse of you in one of his shirts, he instantly realized just how attracted to you he was. Sure he thought you looked beautiful in your own clothes, especially in the short shorts you wore when you helped him wash baby. But there was something about you in his clothes that made his mouth water and his pants grow a little tighter.
It all started when you forgot to pack a shirt to wear to bed on a hunt in Detroit. You frowned and let out a sigh. Of course Dean packed extra clothes and just happened to have an oversized Led Zeppelin shirt that you could wear. It came down to your mid thigh and swam on your body. He couldn’t help but think about what you would look like the morning after. Would you wear his shirt from the night before and nothing else?
When he saw you in one of Sam’s flannels one day in the bunker, he instantly grew angry, and his heart sunk in his chest a little. He thought it was yours and his thing, not something that happened between the three of you. Dean wanted you to only borrow his clothes. He wanted you to be his, and his alone. It was in that moment that he realized that his feelings for you were a lot stronger than he believed them to be.
Weeks later, you were bleeding out in the backseat of the impala, his arms wrapped around you. You weren’t going to die by any means, but he knew you were in a lot of pain and you needed to stay awake in order for them to fix you up. You were shivering from the cold weather outside, so Dean did what he always did. He shed out of his jacket and flannel and wrapped them around you. You smiled softly, thanking him. This time, he told you that his clothes looked a lot better on you than they did him.
You asked Dean if you could borrow one of his flannels one night, only because you had all of your sleepwear in the wash and they weren’t quite done yet. Dean smiled, leading you to his room. He let you pick which one you wanted to wear. Much to his surprise, you picked the one he was wearing an hour ago. He wondered why, and you responded with “I like the way it smells; just like you.”
Dean couldn’t believe what he was hearing. He could feel the tips of his ears heating up as he rubbed the back of his neck nervously. Something completely unlike him. Girls didn’t make him nervous. But he tried his luck.
“If you like the way I smell so much, why don’t you just sleep in my bed? Smells just like me, sweetheart,” he winked.
“Well if you insist.”
Needless to say, as good as his shirts looked on you, they looked even better off of you. And even better the next morning when he knew you had nothing else on beneath it.
Dean loved you in his clothes. But then again, Dean loved you.