I actually would picture it happening during season one, right after the Bugs episode where everybody thinks they are gay and that at one point, Dean calls Sam, Honey and slaps his butt. Then Sam would admit that he liked it and things would unfold from there. Hum, yeah that would make sense right? :P
It could totally make sense! I've long liked Bugs for the very Wincesty undertones you mention. It might start as a joke, right? And then it would get more serious from there...
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