This is the story of my first crossdressing. I was over at Grandma's house with my two aunts. (They are just a few years older than I am. More like older sisters, than aunts!)It was the mid sixties and I was around 5 years old. We were playing in the basement when my older aunt, Cathy, decided that she wanted to play dressup. My younger aunt, Doris, didn't want to, as she was always the one that had to dress. They then decided that I was the one that they would dress up! Just wanting to have fun, I said sure. (I had no idea what that simple sure was going to do to my life!) We climbed in under the stairs and they fished out a beautiful lacy powder blue gown, (in my memories, I call it a prom gown, but it was probably an Easter dress!)
Cathy and Doris had me undress down to my briefs. I wouldn't take them off, no matter how hard they tried, so they just pulled a pair of panties on over my own briefs! Next came the gown. They had me step into it and put my arms in. Pulled it up snug and zipped me in. The gown fit perfectly! I felt wonderful. But we weren't done yet. Next came a pair of aunt Doris's socks and shiny black shoes! And for a finishing touch, a pretty hair clip barely stuck to my "whiffle" cut hair!
We then had a tea party for just the "girls". I stayed dressed most of the day and I think that we even went out in the back yard to play, although I really don't recall.
What I do recall was the feeling that I was one of the girls and it felt right. From that day on, when I went to visit my aunts at Grandma's house, I'd always ask to play dress up!
