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.
