I’d dressed as a woman before, once on Halloween, and two other times when girls tried to flirt by putting me in drag- not that I could pass (or think that was even the point). An ex-girlfriend of mine once asked me to put on a dress, but it was more because she was having her own identity crisis, and I wanted no part of that.
And it isn’t sexual, which is the first thing most people think. I don’t really feel sexy at all, and that isn’t the point. For that matter, I don’t hate my body, or want to be a woman; I’m not pre-op (although I guess it’s made me more… understanding isn’t right, because I don’t think I do understand, or could, really, but more sympathetic). I don’t even go out like this.
If I were a woman doing this, no one would think twice- a college girlfriend went an entire semester wearing only my clothes, and everyone said it was sexy (all right, I’ll admit it, she looked better in my clothes than I ever have in anything).
And I really want to reiterate that I don’t want to be a woman. I don’t like shaving my legs; I’ve got sensitive skin, and a lot more hair than most women ever have to contend with- but it just doesn’t work without. I stopped with the arm and chest hair; it seems less extreme to just wear long sleeves and buttoned collars, and gloves when I’m feeling really self-conscious about my gorilla-knuckles (which is not a relative of the camel toe).
I haven’t found panties I like (and I know, no women actually call them panties, but for my purpose it’s the right term)- so I usually just wear my faded old boxer-briefs. I wear skirts around the house, and at first I told myself I liked the freedom, that it was all about comfort; my self-delusions faded as my wardrobe expanded to include bright colors, and some dresses far more fashion than function (one I’m still dieting to slip into- Rome wasn’t worn in a day).
And one day I was walking through the mall, sliding through racks of men’s clothes as I glanced over the women’s section, too timid to stand in their aisle, and I spotted them. I’ve often told people that love at first sight is just lust (which is totally fine, just not as Hallmarketable), but I fell in love with the shoes. They cost more than any shoes I’ve ever bought; they cost more than any piece of clothing except my leather jacket, but I had to have them, so much that I tried them on in the store. I didn’t care who saw; and there’s no way to describe the way it felt sliding them on, except that I felt like I was in a Disney movie, and that I’d found my Cinderella shoes.
The shoes aren’t glass- because that would be entirely uncomfortable- besides, glass would feel too dainty, too delicate; I’d fear that a strong step would shatter them. But now that I have my shoes, I realize it is about comfort, in a way. I wear them around the house, when I bake, when I clean, playing video games, or just watching TV. It’s like when I switched from tighty-wighties to boxers, but it gives a calm more than physical. I wear them to feel good about myself; I wear them to be pretty.