Crossdressing Plus Adventure

Written by Justina

cross-dressing-adventure-puerto-rico At the age of 13 I worked at a hair salon sweeping the floors and cleaning up. I got the job because the salon was next door to our house in Puerto Rico, and the female owner of the salon liked me.

I was a thin 120 lbs male at 5'2", no facial hair, very little body hair. The female owner and two other hairstylists were always teasing me about how pretty I was, and how they wanted to make me up one day. Well after almost 7 months of teasing, I started to find the idea very tempting.

One day, close to Halloween I told the girls I was willing to be made up. I told my mom, that I was going to a Halloween party, which was true, but I never told her that I was going to go dressed as a female wearing a Catholic school uniform.

The girls had purchased everything, including the white silky panties and the knee high white colored stockings. They spent almost an hour fixing me up and fixed me with a long haired wig that really accented my femininity.

One of the girls drove me to the party, and once there I mingled, but no one recognized me, except for my sister, who already knew of my secret cross-dressing.

A tall dark young man, could have been 16 or 17 years old, approached me and started to flirt with me. We danced, and as the night went on, there were times that I could not resist the turn on and I asked him if he wanted to go somewhere else. He was more than willing and said, "why not, I got my dad's van and I want to check it out."

So we left, and to keep things clean, I acted like if I was a virgin, but was willing to fulfill any of his desires. Well after five minutes of stroking a perfect 8" joy stick, and after a massive explosion, I was pleased and so was he. I have never done anything like it again. Not even my sister knows!