As I have recounted in previous posts, my first real foray into crossdressing was in my sister’s closet as a child. The closet of a high school girl was filled with boundless options for a young boy trying to escape into the world of the feminine: mini-skirts and sundresses, bracelets and necklaces, skinny jeans and short shorts. My goal in crossdressing was to, for a fleeting moment, put myself in the role of one of the girls in my class.
Despite the multitude of options at my disposal, I always found myself trying on the skirts and dresses. In fact, I never once chose my sister’s short shorts or skinny jeans despite the fact that all the girls around me were wearing them. Looking back years later, this puzzled me at first: you would think that in my moments of being a high school girl, I would want to wear precisely what all the other girls around me were wearing. Why did I never choose to wear the skinny jeans or the jean shorts?
In the ensuing years, I have realized that in my fantasies of being a woman I am drawn to those things that are uniquely and distinctly feminine. Both women and men wear jeans; while the styles differ significantly, jeans were still within our society's bounds of "men’s clothing" and weren’t far enough away from what I normally wore to allow me to fulfill the fantasy sufficiently. However, in our culture dresses and skirts are worn exclusively by women. As a man, I wear jeans all the time; but when I was wearing a dress, there was no question that I was wearing something that was societally forbidden to me as a man.
I have found that the things I enjoyed wearing the most, and subsequently enjoy photoshopping myself wearing the most, were the clothes and accessories that were most exclusively feminine. In 2018, some men wear diamond studs in their ears, but chandelier earrings and hoops are the realm of women. Men wear chain necklaces and some may even wear charms, but only women in our society wear pearls. By this same principle, when I am photoshopping myself as a woman, I prefer heels to flats. I always choose that which is most distinctively and explicitly feminine.
Now that my preferred method of living out my dreams of being a woman is through photoshop, this has at least somewhat softened. Now that I can actually physically see myself as a beautiful blonde with a blowout and an impeccable manicure, the fact that I’m wearing skintight white jeans rather than a sundress or diamond studs rather than hoops, has stopped bothering me as much.
Still, I think the key is that in any of the pictures, the picture is explicitly and unquestionably feminine. I spend 100% of my actual life as a man; in my dream world, there’s no need for half measures.