While there is definitely much commonality among childhood stories of crossdressers, there is just as much divergence. My story is just my story. But perhaps it sheds light on a number of elements that easily set the stage for these desires. I’ll spare you my whole entire life story, but I do want to hit a couple major strands of what I think originally led me to the actions that kicked this all off for me.
First of all, I’ll mention mom and dad. I know it’s cliche and very Freudian, but I think a lot comes from the way I saw their relationship and their roles. I saw my dad as mean and harsh with my mom. I saw my mom as weak and unprotective of us. This combination left me wanting to be nothing like my dad and to replace my mom. The replacement mom I had in mind was very pretty, had great ability to capture (command?) her mate’s attention and affection, and also was very strong and secure. This manifested itself in the stereoptypical clothing items that TV and pop culture presented to me as icons of female sexuality- high heels, skirts, hosiery, etc. These became a backdrop for the way I viewed and valued girls even in elementary school.
Probably the biggest single factor leading to the start of my crossdressing at a young age was my crushing insecurity. Much in my upbringing left me feeling unlovely, ugly, and overall very hopless when it came to every gaining the affections of the type of girl I was interested in (i.e. the replacement mom), especially despairing about my prospects of ever myself being the kind of person I wanted to be. Not only did I have the circumstantial obstacles like being pudgy, or nerdy, or poor, or unhygenic, but I also already had the complicating factor of hating the male role that I figured was also the prerequisite to securing a girl’s affections- after all if I can’t be a prize male, what other inroads are there to winning a prize female? As young as 10, I found myself completely vulnerable to the culture’s sales vultures ready to tell me what would make me feel better, look better, be more liked, etc. And the answer, again, seemed to be girl’s stuff (though the culture certainly didn’t market it toward me, they marketted it so well as the well-spring of beauty and worth for girls that at some level I bought in, too). I thought I’d never have a girlfriend and so I began to live a private and inward life of attempting to satisfy myself with fantasies of my mind.
Add to this the condition of my world growing up whereby I perceived that, while I was suffering hardship and hostility and hopelessness, girls in general seemed to have it easy. It seemed to me that all a girl had to do was dress cutely as a girl and the rest of life was niceties and sweetness. I wanted in. I felt cheated when it came to gender, despite any cultural privilege assigned to males. Besides, I was raised with gender equality propaganda (not to say it was wrong at all) in grade school so that defense didn’t really exist in my mind. I thought my sisters had more privileges than my brothers, especially when it came to having their own room, etc. This all came to a head soon enough.
The actual trigger moment, in my opinion, was really one led by curiosity more than anything. I don’t remember having any special agenda at all when I put my sister’s underwear on. It was just sitting there on the floor, nobody was around, and I was curious. I put it on and liked it. This was the beginning of a new pathway of thinking and exploration in my private world. I began to draw good feelings in many ways from the possiblity of pretending I was a girl in my private moments. This moment wasn’t really the first encounter I ever had with crossdressing, but it was the first more or less serious moment. For instance, I faintly recall being 5 or less when being in my sister’s dress, I was either discovered doing it or tricked into it and some of my family members gathered around to join in the joke. It was brief and nothing really hinges on it to me.
There were other little things like seeing a boy dressed up as a girl at school in first grade (he was a 4th grader I think). It was some kind of “wacky day” or something, but it did stick with me as a curiosity and maybe was a seed of an idea. Who knows? The point is that obviously the idea came from somewhere, but the action came from the curiosity and was empowered by my insecurity and desire for that girl/that woman I had placed at the center of my sense of goodness and value and comfort in life. It has definitely been a tough road to unravel for me psychologically- even to piece together this narrative has taken a year of abstinent and diligent reflection- but well worth the journey!