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Now, Dean was a different kind of boy. Always had been, really. From the moment he thought he was autonomous he was picking out his own clothes and dressing himself. Mary thought to let him be, while John hated it. No daughter of his was going to cut off her hair and wear boy clothes! When Mary passed, Dean was forced to let his hair grow and to wear skirts and dressed. He was forced to wear pink tennis shoes and rhinestoned jeans. He hated it, and he hated John for it.
It was until John passed away that Dean shed his old name and clothes to become the man he was supposed to be. Sammy never thought twice about it, why would he? He'd always known and accepted that Dean wasn't female. It was something Sam understood, and stood by Dean about.
The rage used to overcome Dean every time some random called him pretty, or told him he had a girl's mouth. But there was no point in holding on to that rage, so he released it the same day he got his top surgery. He was done. No longer would he be called a dyke for looking the way he did. He used the hormones and worked out to get to where he wanted to be. He accepted his new scars as proof he'd fought the battle of gender identity and societal pressure and come out on the winning side. Hell, he had plenty of other scars from bullet and knife wounds littering his body. What were two more?