Raising two kids...two siblings was nothing easy. Dean was the eldest and knew the most about it. John was never there, and your mother was deceased. So it was all men around the house, except you - you were the little sis! And he always tried his best to understand you even when he couldn't. It was easy for him to just buy some stupid toy and clothes for Sam. But you weren't just another brother. He'd make sure you have the right undergarments, sanitary supplies, and even random stuff like nail polish! It made him resent John a bit more though. The fact that John wouldn't provide for you when it was his job

Sam and Dean had just came back from a successful hunt. They never let you go with them because they wanted you to ge safe as possible. When they came back you were curled up on one of the beds. Dean could immediately tell you were on your period

Dean: "That time of the month kiddo? Wish I could kill these periods and you'd never have one again"

He chuckled and sat down beside you so he could comfort you. He didn't feel your pain, but he always saw your discomfort. He allowed his softer side to take over