I’ve lost track of the many different types of crossdressers I’ve come across – the straight “escape from reality” lingerie lover, the self-professed hetero with overwhelming cocksucking fantasies, the repressed transgender and the pervy pantyboy are just a few. The one thing they all have in common is a secret stash of silky and lacy things that they keep in a secret corner of their closet…or a locked desk drawer, or the wheel well in their trunk. You get the picture.

The Orientation of Crossdressers

There used to be a statistic out there that 80-90% of all crossdressers were actually heterosexual, but when I went looking for a source for that information, only the British ones professed something along those lines. The American ones posited that the heterosexual crossdresser was…mythical. Now my original “research” on the subject is almost two decades in the past and based on a google search done in the UK, lol. I’m guessing that today’s richer spectrum of sexuality (love the term heteroflexible!) might have something to do with this shift in how crossdressers are perceived, but I wouldn’t say that heterosexual ones are a myth!

The Story of “Closet Caitlin”

So I have this submissive sweetheart, I’ll call him Closet Caitlin, who is very sensual and loves silk and satin lingerie. To describe his manner of submission, Caitlin tells me that his favorite blog post of mine is You have to lick before you touch your dick. He is 100% committed to pleasing women. At the same time, he revels in wearing panties on a daily basis and has worn men’s underwear maybe maybe five days in the past year. I can tell you that he has quite the collection, from lacy cheekies to silky hipsters…and a few thongs thrown into the mix for #ThongThursday.

Ever since I dated a crossdresser back in my early 20s, I’ve been curious about how you fellas start with this. I knew that in his college years, Closet Caitlin was rather strapped for cash and took a lot of menial jobs to make ends meet. One of these involved cleaning out the locker room of the women’s swim team. In one of the lockers, he found a pair of sexy black pantyhose. He kept them and I think it is safe to say that he “cherished” them thoroughly, and by the time the pantyhose died of abuse, he was hooked. And now, years later Caitlin’s closet has a section he lovingly refers to as the “lingerie department”.

So what do we have? A guy that adores giving pleasure to women – who wears panties and more on a daily basis. He’s a high-level exec who wears stockings under this khakis for board meetings. But…my favorite habit of his is when he sits on his balcony after dark in outrageous lingerie while smoking a cigar and talking to me in his normal, gravelly voice. Wearing lingerie and heels doesn’t make him want to act like a woman or wish he was one — it just helps him relax and escape a little bit. In a way, it’s no different than a woman coming home from work and changing into sweats and an old t-shirt. We just tend not to change into tightie whities along with it!