When I had earned enough money for college, I started searching for a school I could afford. Then one day, at the local market, I ran into my Kathy, my neighbor, who had taught me a lot in the past. We talked about school, and she suggested that I should attend her college, and she could help me out by renting a room at her house. I was thrilled because I could probably afford to go there. As we talked, she told me how mu...

Years ago, our little town had some unwanted activities. We had a large Job Corp center just up the highway from where I lived and the JC guys would walk into town, past our place. They were mainly black guys from the south and a few Hispanics that were helping with local forest fires. A couple of local girls discovered that the JC guys had money to spend, so they set up a "comfort" area in the local city park, under the...

When my family moved to Oregon, I had no friends living close by. I had just turned 18, and didn't know anyone except a cute neighbor girl. She was maybe 3 years older than me. She was very friendly and we got to know each other over the first summer. The first thing I learned about Kathy was that she was not into guys and preferred girls, something new to me. But it didn't affect our friendship. Kathy and I spent a lot o...

I always loved crossdressing, starting with sexy lingerie and high heels. For many years, I crossdressed in private, a hobby that gave me much pleasure. I was always confused about my sexuality which was controlled by my love of sexy women's clothing. I was unable to wear my sexy things at home and found that it was very exciting for me to dress outdoors. I had located a couple of deserted places, old forgotten parks alon...

I had been crossdressing alone for many years but always in the safety of my own home. But I had always wondered what it would be like to actually meet with a guy. I had fantasized about how much I needed this and I had spent hours and hours watching videos of crossdressers pleasing sexy men. Now, the time was coming for that first adventure. My wife knew nothing about those secret sissy desires, to dress as a sexy woman,...