I’m not sure if most Crossdressers or Transvestites can isolate where this particular interest first came into their lives but I can. Down to the moment.
I was raised in an extended family household consisting of my single mother and my grandparents. My Mom was busy earning her Masters Degree with the hopes of affording us a better life in the future, plus holding a full-time job to support the life we were presently living. My Grandfather held a demanding job so was usually off working and, even when home, was often consumed by the demands of his occupation. My Grandmother was pursuing a degree in Art at the time of my upbringing.
My family was extremely loving and supportive but they all led busy lives too. Without siblings or adequate friendships with kids my own age, I spent alot of time alone. This is not a sad story though and I don’t regret anything about the way I was raised. I developed a fantastic imagination and was incredibly entertained by my thoughts and daydreams in my own head.
My Mom enrolled me in Preschool when I was the appropriate age and this became my first real exposure to kids my own age and people outside my family. I was shy and awkward and generally kept to myself although I got along fairly well with the other kids in my class. I hadn’t interacted with girls before this and they immediately fascinated me. I felt like I could relate to the boys at that age but the girls were a complete mystery. They liked different things from me, they talked differently and they even moved differently.
For Halloween that year, my Mom took it upon herself to make my Halloween costume. She was pretty handy with a sewing machine and we didn’t have alot of money so it made more sense than purchasing something at a store. She asked what I wanted to be and I responded with the character of one of my favorite cartoons of the time: Spiderman.
My Mom sewed together a Spiderman costume for me- it was truly a work of art. Since Spiderman’s costume is essentially a skin tight leotard though, she made the top shirt and shorts portion of the outfit and, for the legs, bought a pair of blue tights.
I don’t actually recall putting on the costume in the morning before school, nor the drive to school or arrival. To be truthful, I don’t remember much about that day at all except for one notable moment which I can recall in crystal clarity. I was riding the swings and something about the sensation of the air rushing against the blue tights of my costume made me take notice. The tactile feeling of the tights against my skin was extremely pleasurable to me. I realized that it was unlike anything I had experienced before. Boys rarely experience skin-tight clothing and the physical sensation of it was fascinating to me.
I distinctly recall that moment, riding the swings and fixated on the physical pleasure of the tights against my skin. It wasn’t sexual in nature but the pleasure was way beyond anything I’d felt before through simply wearing clothing. When compared to corduroys and denim, this felt like euphoria.
As I reveled in the tactile sensation of the tights against my legs, it struck me that, while this was foreign and new to me- girls got to experience this sensation all the time. Something strange clicked in my brain on the swing set in that moment. I realized that I loved wearing stockings and that, unfairly, as a boy I was unable to (aside from the occasional excuse to dress like a super-hero) ever partake in this tactile experience again. Girls were allowed this sensation that was oddly cut off for me. I wondered what other pleasures girls were allowed that I was unable to experience myself simply because I was a boy. Girls were mysterious and fascinating and they seemed to be able to do things that I was unable to do as a boy- like wear stockings and be pretty.
Since that moment, I looked for any excuse to wear stockings. As I began to make friends through my classes and we would play make-believe after school, I’d gleefully volunteer to play the girl role in whatever story reenactment we were embarking upon. If the kids wanted to play Star Wars, I’d opt to play Princess Leia. If we were playing pirates, I’d play the girl pirate. This wasn’t because I wanted to be a girl though. Initially, playing the girl parts simply afforded me the opportunity to slip into a pair of my Mom’s pantyhose in order to piece together the appropriate costume for the role.
While the excuse to wear stockings was my initial motivation, that alone doesn’t make much of a costume so in order to dress up my act, I wound up graduating to wearing wigs and dresses. I liked getting into these characters because they were so outside of my daily norm. I began to use this as a medium to try and look like a girl and even act like a girl.
Interestingly, I never received any friction over my preference to play girl roles from any of my friends or even my family. Nobody ever called me out as being strange or openly suggested I was gay or anything of the sort. It was all perceived as innocent fun and seemingly, perfectly suitable for a boy to play the girl part for our skits and make-believe adventures together. The other kids generally felt relieved that a girl role was being covered. They found it great to have a willing volunteer as Princess Leia for acting out Star Wars because the last thing we all needed was another boy wanting to play Luke.
I’ve never felt like I wanted to become a girl- fulltime I mean. I can empathize with those who feel trapped in the wrong gender but that was never my experience. I enjoy dressing up and playing as a girl but then being able to strip it off and returning to my role as a male. I try to relate it to others as the balance between one’s work mode and holiday mode: Most people act differently at work than the do on holiday but both of those modes are what define a person. Another way to look at it is like the balance between a superhero, who dresses up and can do fantastic things, and their mild-mannered alter-ego. In this sense, the choice for a Spiderman costume to set this whole thing off for me is uncannily poignant.