I would say that "punishment" is the wrong word, and with it, we can draw much stronger negative interpretations that I feel might be appropriate. To me it look

I would say that "punishment" is the wrong word, and with it, we can draw much stronger negative interpretations that I feel might be appropriate. To me it looks like it was a social bet, between two friends, and he is doing it for fun (and to poke fun at himself). I would imagine that would fall pretty close to the definition of a drag queen (particularly the accentuation of certain characteristics, it does look very over the top). Given his appearance, the bet may have been explicit in saying that they would need to to dress in drag (and not "dress as a women"). Some might argue they are different, and in that, he's not saying "it is humiliating to be a women" but rather "it is funny to contrast how I normally look with something so different."