Okay first of all, inspiration for this ficlet goes out to 67chevyimpala for being so amazing and starting an SPN/Teen Wolf crossover which is probably ten thousand times better than mine, but alas, I cannot sleep, so here are the fruits of my labors.
Shuddering, howling cries of grief coursed through a brilliant moonlit night, and Dean grimaced bitterly. It had always been taken for granted that he was righteous - not on a conscious level, of course, but on a deeper rooted plane of existence in which evil was black and white and he could sift the shades of gray into their proper places. Dean Winchester had three purposes in life: saving people, hunting things, and protecting Sammy. When Dean Winchester made a decision to end a life, be it spirit or beast or demon or angel, he knew, or thought he knew, that it was the right thing to do.
So why did this feel so wrong?
He strode back to the Impala, shoulders hunched and eyebrows knit together uneasily. When he reached the smooth relic of his childhood, the first thing he did was open the trunk. Then he removed his father’s jacket and tossed it inside. Somehow he didn’t feel like himself today with it on. He’d never admit it, but Dean didn’t really feel worthy at the moment. He rooted around until his fingernails clinked against a familiar bottle of jack. It was a good thing that Sam was otherwise engaged, because this was one night Dean didn’t want to add to the list of horrible things he’d done for his brother.
Dean sunk into the driver’s seat of his car and drank, letting the freezing night air take away some of the pain – was it guilt? – that engulfed him now. Killing a kid – that was a new low for him. He thought about Ben. He would be reaching that age soon, and Dean regretted not being able to see it. He thought about Jo, little more than a child herself when she died a hunter’s death. His heart hardened, as he knew it would, as the liquor soothed what little soul Dean figured he must have left.
He could still hear a child sobbing as he started his car and drove into the cold night.