I've been crossdressing off and on since I was about 13. I tried on high heels a few times before that (wonderful!) but I would say my semi-regular crossdressing started when I was about 13.
I'd mostly wait until everyone was out of the house, then get my mother's high heels and my sister's dresses. My sister was a year younger than me but a little overweight and her clothes fit me very well (in my fantasies, I would think I looked cuter than her in her clothes). My mother's heels fit me so perfectly, it was almost as if I was meant to wear them..
Once in a while, during Christmas and summer vacations, I would get up in the middle of the night and go into our basement. It was "finished" but nothing fancy. A place where you could watch television and relax. I would prepare for these nights by sneaking a pair of my mother's high heels and my sister's dresses or skits into the basement so they would be ready for me.
I'd dress up and just lounge around in the basement. Rarely, someone would wake up and call down to see what was going on. However, I just told them I couldn't sleep and was watching TV. No one ever came down. I'm sure they couldn't imagine what I was doing.
It was wonderful to dress up. I matured late so even when I was 16 or 17, I was slim and my legs looked wonderfully girlish. I loved putting on a dress and heels.
One night during Christmas vacation when I was 17, I wondered what it would be like to go out walking en femme. The practical side of me said that was crazy. How could I sneak out of the house? What if someone came into the basement while I was out and then discovered me dressed when I came home? It made no sense.
But I was drawn to go out. By the time I was 17, I wondered what it would be like to be seen as a girl. In my fantasies, I would be seen as a pretty girl.
Then, one night, I decided I would go for a short walk. I was terrified that someone would come into the basement while I was gone and I'd be discovered. But the terror was overridden by the excitement, the need to go out.
So, I took the basement back door key. At least, I wouldn't be locked out. I was wearing my sister's minidress, which was even more mini on me, but this was the early 70s and you could wear really short dresses. I wore my mother's wonderful white high heels from Saks Fifth Avenue. I loved the way they felt and looked and loved the way the white heel ended in a cute black rubber tip. Then I put on my sister's winter coat, just long enough to cover my dress.
I hesitated at the door. For several minutes, I hesitated. Then, feeling like I was jumping off a cliff, I went out.
It was terrifying. And wonderful! I loved to hear the click-click-click of my heels on the sidewalk. I loved to watch the shadows I made and the girlish silhouette the streetlights made.
That first time, I barely made it to the corner. Terrified and excited and thrilled all at the same time. I was probably out for a minute or less.
I came back in. No one had come into the basement or even woke up.
It was so good. So exciting. I loved the feeling of being out.
From there, I did more outings on different nights. First, out to the corner. then around the block.
Terrifying, thrilling. Mostly thrillling.Wondering what would happen if I was caught. The good boy, the one who always did his best, who listened, who obeyed. Now, I was transgressing. Wonderful and scary. Loving the way I felt, loving the way my heels sounded. So good.
I kept pushing the envelope. I mostly walked around our darkened, deserted neighborhood.
One night, I felt especially bold and walked down the "busy street". I walked with traffic so that if there were any drivers, they would see my feminine legs and pretty heels and not suspect I was a boy in a dress and heels.
It was so scary. And so wonderful.
I only walked on the "busy street" for a block. At one point, a cab slowed down, the driver gesturing to me, wondering if I needed a ride. I shook my head "no". I still wonder - what would have happened if I got in the cab.
This all happened so long ago. 40 years ago. But I still remember and am thrilled by the experience. It was so foolish, so risky, but so exciting.
Would I have reacted differently if I was 17 today, with all the support and information on the net, knowing that I wasn't the only one who felt this way, who needed to dress, who wanted people to see the real me?