As far as understanding, you might try this thought experiment. Imagine that for whatever reason, you forced to live as a macho guy and could never reveal your identity as a woman. (I know this sounds a bit more what it may feel like to be a transsexual but bear with me.) You may not be a girly-girl, but I imagine there’s “feminine” things that you’d miss, things that you might take for granted now.
Obviously having to do your make-up and wear hose every day isn’t necessarily fun — and I dare say many of us would tire of it if we had to actually do it — but since most of us only get to dress occasionally, it’s more like when you may get glammed up for a special
occasion.
There’s a lot of other motivations for crossdressing, but the opportunity to look pretty and feel sexy I think is a pretty common one, especially for older crossdressers who grew up in an era where male beauty wasn’t openly valued (and “pretty boy” was/still is an insult). And women do have certain advantages here. I may or may not look more attractive en femme — I’ll leave that to others to decide — but I’m certainly prettier since make-up by definition enhances your features and minimizes your flaws.
Conversely, you might try this thought experiment — what if you could get away from your routine and pose as a man for a day. Or probably more accurately, a young guy who just wants to have fun and doesn’t have to worry about paying the mortgage or feeding the kids. I don’t know if there’s any drag kings in your area, but you might try it sometime just for fun (or just go catch a show). The ones I’ve seen offer the same kind of interesting mirror to ideas about masculinity that I’m sure crossdressers must be to women.
