Would you go out for the night dressed as a woman for a bet? Unless your a woman so would you go out dressed as a man? You might already do it.
After asking my wife if bras are uncomfortable she joked I thought you wear my stuff all the time.
Don't think I could but if I did I wouldn't fancy too high a heel and my name would be, predictably, Leanne.
Even if there was no Bet id do it..