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As far as I can remember, this is the first time I thought about gender and sexuality as not being so defined, which came from dressing up as a female for the first time. I dressed as a female for a school play in middle school. I dont remember the name of the play but part of the comedy of the whole thing was all the girls played the guys parts and vice versa. Absolutely terrified in the beginning. My family made the whole situation easier. My dad showed me some photos of him dressed as a woman delivering gag balloon telegrams for my aunt's business. Pretty hilarious. Gave me some confidence. I wore a grey pencil skirt suit of my grandmother's. It was probably very expensive as she was very high fashion. yves saint laurent and Valentino were her favorites. I also had a wig and makeup. I guess you could say that was my first time out. Ha ha. I remember feeling intrigued by it. Thinking about being a different person completely. At the same time feeling ashamed for having such thoughts. A few rehearsals and the big night was a success! After the play we all met in the cafeteria for a kind of wrap party. I had so much fun walking around talking to everyone and reciting some of my lines from the play in character. After the night was over I really didn't think about all the feelings or dressing up again. It really wasn't until my twenties that I started to experiment. Thanks for reading this. Just wanted to share a little.
Sam
Now that's a great beginning , I was just thinking if any other boys after receiving their invitation to join our lifestyle , accepted
Great story Sam!
I had always from an early age wanted to dress as a woman.
I was a late cross dresser. I was 57 and went to a party in a large hoopskirt as a woman of the 1860's. I had a beautiful lacy 115" hooped petticoat, silk lacy pantallettes, A beautiful dress with gray wig, bonnet, string purse, earrings, broach, gloves, and makeup.
I was the belle of the ball you might say. never looked back Have been a cross dresser ever since and really enjoy dressing out and acting as a woman.
As a matter of fact I make a very attractive, feminine and passable woman, a fact I am very proud of.