I steered into the driveway that I had pulled into hundreds of times. This was the first time dressed as a woman. I knew I couldn’t stop what I started. I wasn’t controlling the overwhelming desire to be feminine. It seemed to control me. As a couple walked by, I pressed the remote and pulled into the garage. I watched TV for a while. Though it was late, I decided to try on the lingerie and heels I purchased. After dawnin...

I left Jane’s house feeling exhilarated. I was fairly confident that I passed as a woman, but I only had Jane and Jim telling me that. Maybe they told every client that. As I drove, I thought about what I had done. I not only dressed fully as a woman, and received lengthy instructions on how to act like one, but I had made out with a man and sucked his cock until he came in my mouth. I felt guilty. But not for the reason...

I was in a great marriage. We got along, did fun things, and had a great sex life. My wife, Joann, or “Jo”, knew that I had cross-dressed when I was a teenager. I had told her how my sister, Maggie, had dressed me as a girl for a Halloween party when I was sixteen. I told Jo that she had done such a good job that almost everyone at the party thought I was a girl! One guy had even asked me why I hadn’t worn a costume. I en...

It was nearing the end of junior year. I dressed as a girl so often that I was finding it difficult to act like a boy at school. I did my best, but I couldn’t help being effeminate. I heard references in my classes to a “sissy” and “he acts like a girl.” But I had my girlfriends who knew and supported Robin. Even though I came to school dressed as a boy, they knew I wasn't a sissy. I was a girl. With only a few weeks left...

Katie woke up before Linda the next morning. She put on a robe and went to make coffee. She brought two cups back to the bedroom. She set the coffee down and stared at the person she loved laying in her bed in a see-through light blue nightie, exposing a bra underneath. She smiled and thought, "I don't think he knows that this is a dream come true for me." Katie woke him. "Hey, sleepy girl. Time to get up." "Good morning,...

I started like most "cross-dressers." I was sixteen and I developed an urge to wear my mother’s lingerie. I didn’t know why. I had never heard the term “cross-dresser.” But I did know I liked wearing her underwear. The more I wore her bras, panties, and slips, the more I enjoyed it. I enjoyed the sensual feeling of being feminine. I wore mom’s things every chance I got. And of course, I got careless. She came home unexpec...

As the school year wound down, Linda and I became closer friends. Our study group met weekly and all the other girl’s moms liked me. We had our first group meeting at our house and mom loved meeting the girls. They all loved her and told her that she was just the greatest for letting me be the girl I wanted to be. I didn’t know at the time, but Linda had talked to mom about how she felt about fixing me up with a date. Mom...

That Saturday will always be a fond memory. In just one day, my fantasies and dreams merged into reality. Two days before, I was a boy who wore his mother’s lingerie and pretended to be a girl. After that day, I was transforming into a girl. It reached deep inside of me. As I fell asleep that night, wearing a pink nightie, I felt at peace with myself. When I awoke on Sunday, I lay there. I thought about what had happened....

I had just turned seventeen years old. I was in the second semester of my junior year in high school. I was somewhat of a loner, although I did get together in a study group regularly with four girls from my advanced classes. That was pretty much the focus of my social life. I was an only child and very close to my mother. My father had a job that took him out of town for weeks at a time. So most of the time, it was just...