[My mom and I are out for brunch; at this point, The Boy and I have been dating for a couple of months and it's going really well, so I mention that I'm seeing someone. And then I decide to go for the Big Confession:]
Me: ...and, by the way...The Boy is an occasional crossdresser. I've always liked feminine men, so the crossdressing is a happy thing for me - something I actively wanted and looked for.
Mom: Oh. [Pause.] Can you explain something to me?
Mom: Why would anyone want to wear women's clothes if they didn't have to? They're constricting, they're itchy, they're uncomfortable...
Me: I know, right? But he's willing to put up with it for the sake of being pretty. And, hey, better him than me!
So obviously the Big Confession went smoothly. Frankly, I wasn't that worried anyway: my mom is open-minded* and would be fine with any partner I had as long as he/she/zie treated me well. But it still felt good to get things out in the open.
By the way, after brunch we hung out at my place for a bit. My mom spotted a pair of platform Mary Janes tossed in a corner and said, surprised*, "You have girl shoes!" - then she immediately corrected herself: "Wait...they're his, aren't they?"
And they were.
*And yet, somehow, she manages to be very sheltered at the same time. She probably hasn't heard of many kinks or alternate lifestyles but if someone explained one to her she'd just go "Well, as long as it's not hurting anyone..."
**It's true that I don't own too many girlie-type shoes...but I didn't think clunky dude-shoes were, like, my trademark or anything. Considering how shocked my mom was for those two microseconds, though, I guess I come off more butch than I'd realized. Not that there's anything wrong with that!