I’ve been thinking about this a lot recently. I don’t remember exactly when I started wearing women’s clothing, I think it was sometime around fifth grade. It was always this weird mix of feelings for me. I usually felt out of place in the clothes. Not because the _clothes_ were wrong, but because my _body_ was wrong. It wasn’t that they didn’t fit my body the way I thought they should, it was that my body didn’t fit into them the way I_ knew _it should. As a child, and even a teenager, articulating these feelings in a way that made sense to me was rather difficult. Transgender wasn’t a term I knew and I didn’t yet understand that I _was,_ in fact, a girl. I thought I just _wanted_ to be one. All I knew was that I was always jealous of girls and the clothes they got to wear. Dresses, skirts, high heels, stockings, tight pants. You name it and I was jealous they got to wear it and I didn’t.
I could never actually look in a mirror while wearing women’s clothing, unless I wanted to feel like a freak was staring back at me, but I knew the clothes were right and they felt more natural to me. In my head, I wasn’t a boy wearing girls’ clothing, I was just wearing the correct clothes for me and my gender and the only thing that was wrong was my stupid body.
It was more like cross-bodying, than cross-dressing, but I couldn’t opt out of it.
I’m not hugely into fashion, I don’t read fashion magazines or blogs and I don’t know a ton about it, but women’s fashion has always been interesting to me to a certain degree. I like clothes, but growing up, my interest in fashion was one of those hidden interests that I didn’t dare open up to anyone for fear of it outing me. I would suppress it as much as I could, but when I would go to the mall or Target, or any place with women’s clothing, I would always be stealthily eyeing it up. These days, I supplement this with online window shopping and, every once in a while, I end up going a little crazy on Pinterest. For as long as I can remember, seeing an attractive girl meant I was checking out her outfit as much as I was checking _her_ out. My wife catches me doing this all the time, I guess if you follow my eyes or notice that I often stare for a few seconds rather than just take quick glance, it’s somewhat obvious. She likes to (playfully) call me out on this all the time with little jabs asking if I “like her shoes” or what I “think of her dress.”
The thing about it is, it was never really about the clothes themselves. Yes, I wanted to own them and wear them, but it wasn’t just about wearing a cute dress and a pair of stilettos that perfectly matched my equally cute purse. What I was longing for and jealous of was the right body for those clothes. When I look at clothes online or in a store, it’s not just a simple wanting to buy them and wear them, it’s wanting the body they’re supposed to go on. I don’t just want to have that cowl neck tunic in my closet, I want the breasts, waist, and hips it’s expected to be over top of. When I check out a girl’s outfit, I’m not just evaluating the clothes themselves, I’m noticing out she looks in them and mentally putting myself into her body. I want to be wearing her yoga pants and looking just as hot as she does. I want her butt and her hips and breasts and everything that makes those clothes look so good on her. I don’t want to be her, but if you take my brain and put it in her body, well, life would be perfect.
Cross-dressing implies that I’m not wearing the right clothes or that the clothes are really what matter. The clothes only matter insofar as they’re what I _should_ be wearing. The reality is that I’m a cross-dresser every time I dress like a man. I don’t just want the clothes, I want the body too.