Hi Dan! I'm a 30-something bi woman who recently started seeing a straight guy who likes to wear women's clothes. He's never been open about this with a partner before and while I've been GGG and kink-positive for my whole adulthood, I don't have experience with this particular kink and I want to make him feel as supported (and hot) as possible when he's finally ready to roll it out. I'd love to do find some kink-positive resources but somewhat predictably, Google searches for "cross-dressing boyfriend" turn up a whole lot of OH MY GOD MY BOYFRIEND WEARS PANTIES, IS HE GAY???

What recommendations do you have? Thank you! And thank you for basically being the reason he had the courage to talk to me about this. It's going to be HOT AS HELL.

That's My Girl

My response after the jump....


The best possible resource for a straight guy who likes to wear women's clothes? A girlfriend who thinks the idea is HOT AS HELL. And your boyfriend already has that.

Your desire to show your support by digging up "resources" for your boyfriend is admirable, TMG. But it's just a kink—and a thoroughly harmless, completely run-of-the-mill kink at that. Your boyfriend doesn't have cancer, he didn't lose a parent, he's not addicted to crack. Does he really need a support group? Again: your boyfriend has a harmless kink with an extremely low barrier to entry and, unlike some harder-core kinks (mummification for instance), his kink requires no specialized skill set and presents no risk of bodily harm (unless you regard "ballsack falling out of panties" as "bodily harm"). Pushing resources at him—or encouraging him to attend a support group—may wind up making him feel unsupported, TMG, as he could feel pathologized and/or judged. And you don't want that, right?

So here's my recommendation: Roll his kink the fuck out already! Take him shopping. Buy him some panties and bras and skirts and heels and whatever else turns him on. Ask him to dress up for you—and then fuck the shit out of him.

Okay, okay: here's one resource for you and your boyfriend. Enjoy!