Member-only story
As I spent all the years as a very serious cross dresser, I dreamed of perhaps becoming a transgender woman and what it would be like to live a feminine life.
For many, many years I was my own worst enemy as I learned the parameters of what I needed to work with. First of all, I needed to play catch up with all the girls around me who were already experimenting with makeup and fashion. I remember vividly back in the mini-skirt days how the girls in my class would not so shyly sit and cross their legs to tease all the boys. Little did they know, the affect they had on several boys such as me. I wanted to be them and wear the skirt and panty hose and tease the boys. I was so envious of the stories my wife told me of how she would roll up her skirt when she went to school and was out of sight of her Mom.
I always wondered what if I could ever escape the mirror and experience life the same way she did. Of course I did not and had to set my own course. A course with no guidance or peer pressure on how I looked. What if I could live as a woman remained an illusive dream. To keep my frail mental health balanced, I tried to improve my presentation on my own As I am fond of saying, I experienced quite a bit more error than trial as I slowly learned to express and embrace myself as a novice transgender woman. To add to my excitement, my wife and I purchased our first computer and I was able to learn about other…
