No one needed or wanted to see this man in a dress. For that reason, we have all lost. It makes you wonder what kind of bet this was. It could have been a sports bet, or something that came up during a game of poker. There's also the chance that this guy got hit with one of those surprise bets where someone knows information you don't, so they bet you on it. Then they pull out a newspaper. "I bet you Trump is separating undocumented children from their families." / "Stupid. I take that bet." *five minute later* "Can you button my dress for me?"
Let me get very woke for a second. You can tell me how annoying it is. This "punishment" is transphobic and homophobic, and probably another phobic too if I looked harder. Why is a man dressing as a woman a bad thing? My woke side calls foul!