I am not into gender swapped characters. That’s not an issue. Everyone can like what they like. But I think one of the reasons it bugs me is when I see the art/fancasts/etc, Dean is portrayed as massively buxom with a shirt down to there. 

I… just… would Dean’s character change that much? He wears ten layers of shirts, and suddenly hello! boobs! and the shirt(s) became a low cut singlet?

Canon Dean uses his sexuality to his advantage. He knows he looks good and knows how to use it to get what he wants.

I don’t think that would change if Dean was female. She would use it and flaunt it, though I do think she would be very careful about long hair when she was hunting. I doubt she’d leave it down if it was long, and most likely would keep it shorter like young Mary and pull it up when she was about to hunt.

Boobs… I’m not too sure about that. Mary isn’t all that big, but again I think female Dean would play it up – maybe use a push-up or padded bra if she didn’t have much up top. Not only would she probably like sex as much as male Dean, but she would use it to get info out of witnesses and targets.

Also… I just like the idea of a female Dean, and there’s so little of it that I take what I can get.