I don’t know why anybody else likes wearing clothing that’s usually associated with the opposite sex. There could be lots of reasons, and the only way you’ll know for sure (and maybe not even then) is to ask the person — except that wouldn’t be polite, so you’ll never know, period.
It could even change as the cross-dresser goes through life. It could be for erotic arousal sometimes, at other times it might be a way of earning money, or just for fun.
One of the reasons I do it is so my outside will match how I’m feeling on the inside. When I was young, I could only allow myself to feel feminine when actually dressed as a girl — but today I sometimes feel quite feminine, if I choose to, even when wearing my Farmer John jeans and plaid work shirt. So the cute outfits are a way of intensifying the inner feeling by getting rid of those confusing masculine cues and just being all girl.
The older you get, though, the harder it gets to pull it together. If I look in the mirror, what I see doesn’t mesh very well with how I’m feeling. Girl, if you’re 22, or even 32, and feeling insecure about how you look, I have some advice: Pull up your panty hose, sling your purse over your shoulder, and get on with it! You’re not going to get any better looking while you hide behind closed doors.
I would recommend that you learn about fashion and makeup so you can look your personal best. And maybe take off those extra pounds while you’re at it, okay, darlin’? You will do neither yourself nor the transgender community any good if you go out in public looking like something that floated up off the bottom of the lake after about a week under water.
Do yourself a favor and get it right — but then do yourself an even bigger favor and get it in gear! Strut it while you’ve got it, because it will go south on you.
I’m getting a little jowly, and my neck is sagging, and the bags under my eyes and the veins on the backs of my hands … yuck. I’ve still got great legs for an old broad, but who’s going to look at my legs?
It’s almost easier not to bother with the girl-stuff. Just do the guy thing. It’s easier, but it’s sad too.
I know that all older women (most of them genetically female) face these same issues. It’s not just me. The difference is, a genetic female who has never considered herself anything but female, who is now over 60 and looks it, doesn’t default back to feeling male. Or … I don’t know, maybe I’m fantasizing that the grass is greener on the other side of the fence. I’ve read that some women who have had mastectomies, for instance, feel less authentically female than they did before. Their gendered self-concept is closely tied in with their body image. And the gods know there are enough dumpy older women wandering around who are surely devoting a lot less attention to their appearance than they did when they were younger, and probably if you asked them they’d say they feel less feminine now (and are sad about it).
Maybe I just need a boatload of fashion tips so I can look my personal best, whatever that is at this point in my life. Maybe I’m just feeling sorry for myself because I don’t know which foundation suits my complexion, or how to find a wig that has a flattering hair style, or where to buy a skirt that looks good with a 36 inch waist and 38 inch hips.
Maybe there are still ways to bring the outside a little closer to the inside.
