When I was a kid, I tried cross dressing as a girl. Mostly I was just curious what it would be like to dress as a girl. It was summer and my mother was at work, so I had the house to myself all day. I decided to try some lips stick, and that was fun. I was blond and very fair and discovered that I actually made a pretty attractive girl if I combed my hair just right and did a little makeup. Anyway, it was fun and kind of a turn on. I tried painting my toenails and I sort of liked that. Finally, after trying this out for a few weeks, I began to wonder if I could get away with dressing up as a girl and going out in public that way.
I put on a sleeveless striped top and wore one on my mom's bras (she wasn't all that big), and wore some cut-offs and flip-flops, after having painted my toenails a shade of deep pink. Bravely I went out the door and walked down the street. It was a week day so nobody was around. It was a considerable turn on doing that, and it gave me a very stiff erection. When I got home, I got naked and masturbated to a wonderful ejaculation.
Well, this was such an enticing turn on, that I tried doing it some more. I felt daring enough to go down to the park and walk around, and I saw some boys noticing me, telling m that I was quite successful in my diguise. Encouraged, I took the bus downtown dressed as a girl. No one even looked twice at me, and just took me for a girl, although I kept thinking how surprised they would be if they knew that I had this huge erection in my cut-offs. I did this a number of times and it was always fun and a real turn on, and I enjoyed masturbating so much after doing that.
This went on for about two years, and then I sort of tired of it, and started being afraid that I migth meet someone that I knew, so I eventually stopped. Today it's still my little secret and no one knows.