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Summary
After Dean hit puberty he wanted to learn every way to make himself feel good. Eventually he learns that he can use his sister to help make him feel better. So Dean takes every opportunity to do that, especially when he knows their dad won't wake up.
This fills a supernatural kink meme prompt. The original prompt is:
Sam's 8-10. A teenage boy has needs. Whenever money's tight and dad makes him and his sister share a bed, Dean waits until everyone's fast asleep then uses Sammi to get himself off. Usually he'll just rub himself against her, quick and messy, but when he knows dad's truly out of it, he'll do what he always wants to, take his time and fuck her little pussy.
It can be found here.