So my thinking is it happened before Sam went to college. My thoughts on it are based off of Sam's disconnection to the family after he left, and how well Sam and Dean know each other.
I have siblings, we are not anywhere near that close. Sam and Dean connect at a different level. Also it's common for gay/bi/str8 boys to reject their first experimental experiences and try to run away or hide from it. The story defines it as being Sam not wanting to live the life of the hunter, but I think the wincest is what's underlying. And maybe Sam starts opening up more as he begins to accept their secret, and instead of focusing on what happened, sees the friendship potential. . . . ONLY for things to get awkward again when they try to take it back to the sexual. Secrets, lies, and sleeping with demons to flush the naughty naughty thoughts out? I dunno. Just one boys opinion.
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I have siblings, we are not anywhere near that close. Sam and Dean connect at a different level. Also it's common for gay/bi/str8 boys to reject their first experimental experiences and try to run away or hide from it. The story defines it as being Sam not wanting to live the life of the hunter, but I think the wincest is what's underlying. And maybe Sam starts opening up more as he begins to accept their secret, and instead of focusing on what happened, sees the friendship potential. . . . ONLY for things to get awkward again when they try to take it back to the sexual. Secrets, lies, and sleeping with demons to flush the naughty naughty thoughts out? I dunno. Just one boys opinion.