I Was Dared To Dress In A Dress

I can't say it was really a dare, more like a challenge, my girlfriend at the time was selling avon, she said she wanted to see how good she could make me look, I was up for it, but wow was I blown away when she finished, I looked great, she said I challenge you to put on your dress, and dress for the day, I want to see how many people we can fool, I had no idea that this meant going to the mall and doing some dress and shoe shopping, I must say though that if anybody had any idea that I wasn't a woman, they didn't say it out loud.
mistresscathy mistresscathy
46-50, T
3 Responses Jul 28, 2010

i got started with makeup when i found my mother's bag of sample avon products she sold. i have never looked back. The joys of a young boy of 11 to have makeup on and kiss pics of both men and women.

I was slightly taller than my girlfriend but not by much, but no her clothes were to tight for me, so she had me buy my own, she knew I crossdressed before we started dating.

Wow what fun.. did you fit in her outfits?