My mother also says I was an especially clingy baby, very sensitive and jealous of the attention my mother would give my little sister. My mother says she had to carry two babies, one in each arm, and I always insisted on being carried. I really don't remember that, but I do remember that my sister was a pampered little princess and I was jealous of the attention and pretty things she would get.
My first cross-dressing experiences occurred when I was about 3-4 years old. This consisted of playing dress up with my mother's clothes. My mother did not approve. I remember telling my mother that I was playing "mommy". My mother was upset because I was damaging her clothes. Now my mother was a talented seamstress. I remember one day when she was making a little dress. She would call me over and measure it against my body making sure she had all the measurements right. At one point she removed my clothes and had me put on a little slip/petticoat and pulled the dress over me. It was a lovely party dress. I was thrilled. It could twirl. (This was in the early 1950's and petticoats were the style.) I was dancing and twirling around the room, as my mother laughed. Now my older brother was a bit of a bully and he suddenly walked in. He fell on the floor laughing and pointing at me. In an instant my joy changed into horror. I broke out in tears. "Take it off. Take it off." Now I was crying and my father came in, and there was loud discussion. I never wore that dress again, but would see it again. The dress was given to a girl across the street, and she would wear it to church. My brother would point it out to me. "Look, Linda is wearing your dress." and then he would punch me in the arm. It was a form of aversion therapy.
After that my cross-dress was always in secret. During those years the cross-dressing was like playing make believe. I believed that all parents preferred girls because girls were nicer, prettier, smarter and just better. I thought girls had it better in life. Girls didn't get punched. Girls never got into trouble with their parents. I thought that my mother would love me more if I was a girl. When I could cross-dress it was a fantasy land where there were no problems, and everyone loved me, and life was pretty.
I never questioned my gender. I always accepted that I was a boy. I just admired females and feminine things were fascinating. I thought that all boys were like this and secretly cross-dressed, but this was a taboo subject that boys could never discuss. Then when I was around 11-12 years old everything suddenly and dramatically changed. It was testosterone. I was beginning puberty. My mother kept some of her vintage dresses in my closet because they didn't fit anywhere else. They were hung in plastic liners, inside a zippered storage container that hung in my closet. I was always aware of these items but one day I just decided to try one on. I chose a pretty red velvet dress with a rayon liner, just because it looked so darn good. It was so very stimulating to touch and as it came over my skin, I was shaking all over. <snip> I only wore it for two minutes. My entire body was about to explode and I was left wondering, "Wow, what just happened?" It was different than my innocent childhood cross-dressing.
I was immediately addicted. My adolescence period was then one of a quiet, introspective boy. I was a sensitive boy who had poor social skills, and was insecure around girls. I could escape by cross-dressing. My brain was interpreting cross-dressing as actual contact with a female. My brain would then release a host of neurotransmitters (dopamine, serotonin, oxytocin and others) which produces sensations of well-being, pleasure, sexual gratification and bonding. It would affect the reward centers of my brain, instant gratification, and thus it would mimic the addiction pattern.
Today I continue to struggle with my cross-dressing. I am married, have children, and my cross-dressing is considered a negative in the marriage. I let my wife set the limits and do my best to live within her boundaries. So far, it has worked. I continue to be very introspective and have questioned my cross-dressing daily. I have come to terms with myself as a normal, healthy, heterosexual male with one little neural connection which makes cross-dressing comfortable. It's that simple.
** Post edited to remove sexually-explicit references as per our rules.