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When Sam told Dean she was a girl, he asked if she wanted to look like Cyndi Lauper. Sam scrunched his face up at it, then, and still does. No, not Cyndi Lauper. Maybe Joan Jett if she was Madonna. Maybe just Sam Winchester. Dean wasn't distasteful about it. Stupid, yes, but never hateful the way Sam expected. He asked her if she needed anything—what, makeup, bras, panties, perfume, what do chicks dig?—and Sam could barely swallow. All she asked of Dean was to not tell their dad. He didn't. John would die assuming he had two sons, really. Sam figured that was better, it was always going to be better that John knew nothing about Sam. About Dean. About Sam and Dean.
When Dean saw her for the first time in years, he asked if Jess knew. Of course Jess knew. Proudly. Flaunted Sam Winchester off as her girlfriend, her genius girl, her girl. It kicked Sam in the gut every time. She loved her hair. Her blonde, flowy hair and her eyes—God, her eyes felt like an angel's gaze. She smiled at Sam, did her nails, styled her hair, kissed her and kissed her and kissed her. Dean did, too. He would kiss Sam, muttering into her skin in the dead of night, when they were barely living. Sam, Sam, Sam, like a prayer, My beautiful sister, like he meant it, and it always came back to Sam and Dean.
Sam assumed Dean always wanted a sister. Not that it mattered. As long as Sam was Sam, Dean was happy. He bought her trashy dollar store perfumes that their dad scrunched his nose up at, got her nice clothes when he could. Kissed her from neck to knee, beautiful sister, he'd mutter like it was the only thing on his mind. Fourteen. Sam was fourteen when she told Dean and it changed most things and nothing at all. Beautiful sister, my sister, my girl, my genius girl. His. Sam reminisced on it most nights. Never told Jess a thing about Dean.
Sam watched Jess burn on her ceiling and she felt alone all over again. Beside Dean, in the Impala, it felt… different. Brand new. Dad wasn't there, Jess wasn't ever going to be there. It was Sam and Dean all over again. She didn't dress any different, even if Dean suggested it a few times. There was comfort in the usual. She grew her hair out on the road, though, chopping her hair messily when stress swallowed her whole. Impulsive chops, layered with uneven bangs, done in a motel room somewhere in the Northwest. And then it sort of hit her, a solid four hunts in, this is what she's meant for. Saving things, with her brother. She was meant for her brother.
The demon blood hit her hard, too. Maybe she was always a freak, different, and Dean just said the quiet part loudly. Very, very loud.