Highway in Heels

Highway in Heels
By Sabrina G. Langton

*Stories from the real world 1
This story is autobiographical.

When I was 20 years old I used to drive a van for my parents from Brooklyn to Tarrytown New York once a week to drop off merchandise for retail shops in the area. I always had a full van on the way up, but on the way down the van was almost empty. It was the summer of 1981 and I was given twenty-five to forty dollars, plus gas to make the drive. I did this for the entire summer while I was home from college.

I was a crossdresser for 11 years at this point and I was very good at it. Even when I wasn't dressed as a girl, some people were confused, I always had long hair and sometimes put it in a ponytail. I lived in the basement of my parents’ home and I had plenty of privacy. I was usually the only one home and the house was often empty. My father had a huge warehouse filled with random things and when anything that captured my feminine outlook and was in stock I made sure that I had access to it. My wardrobe at this time was pretty big and I had so many dresses and skirts and blouses that I had hardly any room for them. I used to keep some of my clothes and various pieces of lingerie in a box in my van.

I remember once we got a huge shipment of Candies. They were perfect sexy heels for younger women. I had 14 different pairs and I wore them all out, they were so sexy. I also had dozens of sunglasses, fishnet stockings, leg warmers, and tube tops. Well, it was the 80's.

When I had nothing to do the rest of the day after a trip to Tarrytown I would go in the back of the van and get dressed up and make the drive back dressed as a woman. It was by far my favorite thing to do, and I did it a lot. I had about an hour drive and I loved teasing the truckers that drove next to me on the highways. I wore my Candies and I would flash the truckers my nylon legs and even my panties. Then when I got nearer to my home I would park and take all my female items off. My block when I was a kid was so busy I couldn’t chance anyone seeing me dressed as a girl.