This letter was originally published on October 9, 2008:

I'm a 23-year-old bi male mostly attracted to women. I have a fetish for cross-dressing, but only in private, as I live in a town—Tucson—that's small enough that I might get recognized if I went out "dressed." I'm not having any luck finding a woman interested in having a long-term relationship. I've been in a few serious relationships with women in the last few years, and all have been GGG for every kink I threw at them. But when I work up the nerve to float guy-on-guy stuff or me wearing panties, I always get "Ewww, gross!" I've tried online options to no avail. Where can I meet my dream girl who will watch me with a guy while I am wearing a skirt?

Closet Princess Seeking Princess

My response after the jump...

The women you've dated were up for every kink you "threw at them," CPSP, until you tossed out your actual kinks, the ones you care about, the ones that make your dick rock hard, and then you got ewwwgrossed every time.


I'll bet you're breezy, charming, and funny when the stakes are low and you're discussing kinks that aren't your own. But when it comes time to share your kinks, CPSP, I suspect you get nervous, sweaty, and tense. Because the stakes are much, much higher.

Of course, bisexuality and cross-dressing—as opposed to, say, a thing for feet or high heels (on her)—are going to be higher hurdles for most women. The former because it taps into thoroughly reasonable fears (what if you're gay and not out yet? what health risks is she running if you're out there sucking off other dudes?); the latter because for some women, seeing their boyfriends engaged in what they perceive to be thoroughly unmasculine activities—their asses panty-clad, their mouths cock-stuffed—amounts to a deal-breaking turnoff.

But there are women into your kinks, CPSP; it's just going to take more than one or two internet searches to find one. And there are women who might be willing to go there for you, if they love you enough, but you'll never know if she's the one if you shut down after that first "Ewww, gross!"