What us the best bet to lose if you like to crossdress?

Answer 1

Bet a girl on some kind of athletic contest.

Have the forfeit be that if you lose, you have to wear a dress, or maybe even a Cheerleading uniform. If you're lucky, she'll suggest it and save you some trouble. If not, try talking up the "boys are better athletes than girls!" angle until she suggests something with you in girl's clothes if you lose. She will see it as poetic justice for thinking you're "better" than girls.

If you want to go all out, keep talking about how there's no way you could lose to a girl. That will have her keep suggesting upping the stakes, which you'll get to agree to. If you started with having to wear a dress if you lose, you can get her to suggest that you don't just have to wear a dress - you have to get a girly makeover first. That's fine, because I know I'll never lose to a stupid girl! Oh yeah? Well, if you lose, you not only have to get a makeover, you have to come to the mall with us. That's fine, I won't lose. Oh yeah? Well, if you lose, you have to buy a dress at the mall and wear it the next day, all day! That's fine because I won't lose.

Then, of course, you lose. You want to do it in a way that doesn't make it obvious that you're trying to lose. It will be more fun if the girls doing your nails and makeup don't know that you're enjoying every minute of it.