The first time I found myself asking this question was about 18 years ago, when I unearthed a bag of decrepit women’s clothing from my then-boyfriend’s closet. I knew he had briefly lived with a previous girlfriend, but these were definitely not hers. It wasn’t hard to get him to confess his crossdressing secret, and to both his credit and mine, we both knew pretty quickly that it wasn’t a relationship dealbreaker. Instead, it became a curiosity, an experiment, a novelty – and since I know you’re all curious, it had nothing to do with why we broke up.

What is a Crossdresser?

The typical crossdresser is a heterosexual man who enjoys wearing women’s clothing and possibly also make-up, wigs, heels, etc. Yes, that’s right, I said heterosexual. He is no more or less likely to be bi or gay than a non-crossdresser! To my surprise, I discovered that although it seems like a man would do this purely for a sexual kick, that’s not usually the case. Whaaaa?? Well, you guys tend to start doing this quite young, when it doesn’t have any erotic meaning at all. Then, as a full-grown man, it becomes a form of escapism, stress relief, that sort of thing. That ex I mentioned above? He said he fantasized about having sex while crossdressed, but then he backed out of trying more than once. So I figured there must be something to this “non-sexual” angle I hadn’t considered.

Can Crossdressers Be “cured”?

I hate that terminology – crossdressing is not an illness, medical or societal. It’s more accurately interpreted as a state of being. But it’s such a misunderstood one that men keep it very much under wraps and rarely divulge this quirk to anyone but, well, a phone sex mistress like me. So the short answer is “no”, as they are prone to the crossdressers’ purge cycle (which makes all of us ladies here sad, especially since some of you have fantastic collections built up!).

In closing, I do wish society as a whole understood more about what crossdressers are and aren’t all about…but until then, at least you know where to find some smart ladies who “get you”.

NOTE: Although the picture in this post is not me, I have *definitely* done the underwear swap with not one but TWO boyfriends, woohoo!