Lost bet crossdress

Answer 1

I've tried a few times to lose bets so that my girlfriend gets to crossdress me!

I did something similar. She wanted to play me at tennis (she's really good, actually). I said "You're on!" and something about how I wasn't about to lose to a girl because boys are better athletes. She was actually the one who suggested betting on the game. I said if she lost, she had to dress up like a cheerleader and do a cheer for me. She agreed, saying if I lost I had to do the same thing! I said it was fine, because I'd never lose to a girl. "Oh, yeah? Well, if you lose I get to give you a makeover, and you have to wear your cheerleader outfit all day!" I agreed at once.

I didn't really have to do much to lose. She's actually better than me at tennis. I had an amazing day. She said I looked so cute that I should wear my cheerleader outfit again for halloween. I "reluctantly" agreed.