Crossdressing AwakeningThe first time that I recall having an interest in crossdressing was when I was about 10 years old. It was Halloween time and there was a costume parade at school. For the life of me, I cannot recall what I wore, but there is one costume that I vividly remember!
There was this one boy who dressed as a girl. He wore a soft pullover sweater and pleated skirt. He had on white anklets and pointy flats. He wore a delicate pearl necklace and had on a pageboy wig. He seemed to be having a lot of fun and I remember he had a cute smile. If you didn't know, you'd think he was a sweet little girl.
I guess I had a schoolboy crush on him. Even though it was years before puberty for me, I remember having this "funny" feeling inside when I saw him. Kind of an excitement and thrill that I'd never experienced before. I was not one of those boys who "hated" girls. In fact, I had several female friends. But I found myself strangely attracted to this boy because of what he was wearing.
It is only looking back now that I realize that this was my first introduction to crossdressing and the feelings of excitement that it aroused in me.
jennyla73 36-40, F 13 Responses 21 Mar 25, 2012