Hi, my name is Margaret and I’d like to tell you about my first ‘real’ cross-dressing experience. I had played the part of the daughter of Rosie O’Grady in a school play – it was an all boys school and since I was always one of the shortest boys, I’d get picked to play the girl. That first time I was 7 years old and I absolutely loved all the attention and the way I felt and looked. Of course I couldn’t let on.
When I was about 12 years old, our next door neighbor asked my mother if I would be willing to help her alter some of her clothes, as she did a great deal of sewing and alterations etc. She had just provided me with a dress for another school play and knew that I was her size.
My mother agreed that I would help, without even consulting me. This lady was always very good to us and mother felt that it was the least we could do.
The next afternoon, after school, I went next door and Polly, our neighbor, thanked me for coming in to help her. I wasn’t aware of exactly she wanted to do until I got there. She had a few dresses hanging on a hook on the back of the door, and told me that she needed to hem them and take them in a bit. She wanted me to put them on so that she could use me as a manniquin.
Initially she asked me to remove my shirt and pants, which I did. She put the dress on me and decided that she had to put a stuffed bra on me so that the dress fell properly. She and I were the exact same size. She began hemming the dress and I was absolutely loving the feeling I had wearing this dress.
The next day I suggested that she would get a better idea of how her dresses would look if I was wearing heels. She smiled. I think she knew that I was enjoying this little sojourn into pretending to be a girl. She said, “That’s a very good idea. In fact, in order to fit the heels on properly you’ll need stockings and garters”. I had no objection to that! Finally she said, “Why don’t I put a slip on you, then the dress will fall just right”. She got me all dressed and proceeded to do her alterations. When she was done she was going to give me some hot cocoa and cookies. She said, “Go inside and change and I’ll have the cocoa ready for you”. Instead of changing, I posed in front of her full length mirror, loving the way I looked.
I went out to the kitchen and she wondered why I hadn’t changed. I told her that I liked the dress and the way it looked on me and didn’t want to change yet. She was wonderful! From that day on, whenever I went to help her, she would get me all dressed in female attire and eventually put some make-up on me and even a wig.
She never told my parents and continued to have me come to her apartment regularly dress me up, even when she didn’t have any alterations to do. In fact, she had altered a few outfits just for me! That was one of the greatest experiences I ever had with cross-dressing…