First Crossdressing Experience

It was a dare to wear a bra to school (I was 13) I wore a bra to school under my shirt. The guy that dared me said thought he'd chicken out. Someone else said he must be gay. When I was 15 I wore both a bra and dress in a Zellers cafe. Nobody said anything but there were a few looks and my youngest sister was there wearing a jean skirt. She pretended not to notice. I didn't have the nerve the walk through the mall with the dress on I changed in to my pants and shirt in the washroom marked handicapped.
aquarius3 aquarius3
3 Responses Oct 29, 2011

You were brave to try something new with yourself. And I think your sister was nice about it and not embarrass you. I'm sure she helped out a few times with the clothes.
I started cross dressing last month as male, and I got compliments on my new men's clothes. I enjoy being out and about while wearing them, and started to go out more often.

That is great, Aquarius. Obviously your youngest sister now knows you crossdress and no doubt it makes it easier for her to buy you gifts on those special occassions.

It was my young sister and she never thinks of buying anyone anything! She just thinks of herself! Wants everything and bosses people around and she wonders why she has no friends.

What a bummer ... it seems like every family as some one like your sister, totally and completely self-centered seeming to think that the world revolves around them.

That sounded like fun and an adventure for you.