I was the first born. My Mother wanted a girl so she dressed me as a girl until I was 5 years old. I never got a haircut and had long natural curly hair. My Mother dressed me in frilly little dresses and put bows in my hair. When we went out people would tell me I was a pretty little girl. When I was about 6 my Mom took me to the barber and he cut off my hair. I then had to start wearing boys clothes. I was so confused and sad. I thought I was actually a girl up until then.
When I was 16 my girlfriend was a cheerleader. She invited me to her house one Saturday. She wanted me to wear her cheerleader outfit. It excited me so I said yes. She gave me a pair of her panties, bra and outfit. When I put on her panties I was shaking with excitement. I got dressed and went into the kitchen. Her mother was there with makeup and wig. She did a very good job. I found out later she worked for a cosmetic company and did makeovers for a living. I looked in the mirror and have been crossdressing since. Two weeks later I went to her house early Saturday morning. She was ready to dress me up and go out. I about flipped out. This time she gave me a skirt and sweater. She also gave me a panties and a bra. Again when I got dressed up her mother was waiting with make up and wig. After she was done with my makeup she painted my fingernails and toenails pink, gave me a necklace with a pink heart. This time I really felt like a girl. It was so surreal. Her mother was very good with makeup. I only weighted about 95 pounds and was very petite, I had the body, face and voice of a 16 old girl. Her mother took us to the shopping center and dropped us off. I walked in very scared and excited. After about 15 minutes I noticed no one was even looking at me.
As the summer progressed I had bought my own clothes and even some great shoes. I left everything at my girlfriends house and spent almost every Saturday there when I was 16 being a teenage girl. It was the best summer of my life. I felt so powerful, pretty and free.
The next summer I got my drivers license and moved on.
I got married 4 years later and immediately told my wife I was a crossdresser. She was very supportive and even helped me pick out my clothes. I began going out in public again. I would go to the university library as a female to study. I even went to a large auditorium type class as a female several times. I go out in all situations and feel comfortable as a woman.
My wife and I have double dated with 2 of our male gay friends, Tim and Greg, who we call our boyfriends. Mine is Greg. They were not comfortable going out together. My Wife and I were also not comfortable going out together. The four of us decided if we went out as a double date we would be less noticeable. We did this for about five years. We were all friends and there was never any physical contact except holding hands. We graduated from college and moved away. We kept in touch with Greg and Tim.