The Man in a Dress: Why is Cross-dressing Sometimes So Hot?

OMGby Madeline Iva

Sometimes we find a man with a mixture of male and female features hits our evolutionary bullseye.  (I want to boink him but I want to cuddle him too! See every boy band ever created.) But why is it that sometimes cross-dressing is so very hot?

My love for/obsession with cross-dressing goes back, waaaaay back to the dawn of those hazy/shameful lustful feelings reading romance novels as a teenager.

In Georgette Heyer’s romance THE MASQUERADERS, our heroine ends up in a state of arousal and confusion around her hero.  It deeply affects her that he includes her in his sphere because they get along so well. He simply enjoys being around her.  I find this very sexy–it’s her brain that counts–her inner substance is compelling to him.  It’s not about her looks or femininity.  It’s not about how much she conforms to a societal standard or ideal.

Meanwhile, HIS decisive confidence in his own sexuality cuts through the gordian knot of a complicated seething desire he feels for her after being around her for a while. And once he feels what he feels, and sorts that out, he sees clearly what has to be going on: she’s not a young man after all.  Beneath her brazen ruse he sees her vulnerable side. Oy. SO sexy.

The only regret I have about this book is that at this stage readers could use a super-hot sex scene.  But that’s not how Heyer rolls.

Towards the end of high school I got a snootful of Dr. Frankenfurter in THE ROCKY HORROR PICTURE SHOW.  He was sublime.  And just when you thought he wasn’t interested in women at all he proved himself *very* interested–and skilled.  It was the stealthy seduction and attack that I loved just as much as the naming and claiming of his own scandalous desires.  Someone with this much confidence, with this much unappreciated genius, could also show you his intense diva side–his wanting to be wanted, his desiring to be desired–and still come off as the hottest guy in the room through sheer force of his sexual charisma.

There were other cross-dressing moments that imprinted my youthful psyche in the early 90’s–aside from that cross-dressing classic SOME LIKE IT HOT.  The ending of SOME LIKE IT HOT is probably the most perfect ending to a movie ever made and a sine-qua-non of what romance is truly all about.

David Duchovney in drag & his lazy seductive voice.
David Duchovney in drag & his lazy seductive voice.

But back to the 90’s.  I became catching glimpses of David Duchevony on TWIN PEAKS.  I wasn’t watching the show, so it was just glimpses of him in clips. I think the idea was that he was originally cross-dressing as an undercover assignment for the FBI, but that the cross dressing got away from him and took on a life of its own.  I was captivated.  When he was dressed as a woman it let me focus on his ultra-male voice.  That amazing low, rich, lazy voice–is *so* sexy.  And being a woman, he presented his vulnerable soft side first.  I found it to be a major turn on.  It’s sort of similar to a really hot guy laying back and saying ‘you can do anything you want with me.’  This must be what’s appealing to men when women are vulnerable. And this too, to me at least, is the appeal of a cross-dressing guy.

Hey, watch the wig.
Hottest Pedro Almodovar sex scene ever???

But there’s another appeal as well, I think.  Around that same time a movie came out called HIGH HEELS.

In HIGH HEELS Victoria Abril’s character grows up with a mother who is a singer–and clawing her way to the top.  Abril’s character therefore, grows up lonely and neglected as a child, in a world where men are pretty much pigs.  She is so hungry for mother-love eventually she marries an ex-boyfriend of her mother’s.  She is so mother-hungry, she also finds a cross-dressing cabaret performer who dresses up as her mother and who befriends her.   He is her one and only friend until the night when she’s helping him undress after his act, and his desire her for overwhelms him.  Soon they are f***ing in his dressing room.  It’s a hot, mind-clearing boink for her, yet he’s secretly in love with her.

It was such a hot scene. Something about the permissive atmosphere around them seems to let secret desires out.  Something about cross-dressing–an act of letting go and just saying yes to who you are on the inside–enables their intimate friendship to suddenly ignite into a hot connection.

The dark desire for a hot cross-dressing man isn’t just about seeing his vulnerable sensitive side first through friendship and it’s not only about examining/letting out out secret desires, it’s much MUCH more subversive than that.

I had to go back and watch THE ROCKY HORROR PICTURE SHOW again to really get it. In mirror scenes, Frankenfurter puts both Janet and Brad in the same situation and they both react the same way.  Their desire to be taken by surprise and to give in to naughty temptation are exactly alike.  Underneath the gender roles we’re assigned, aren’t we’re all the very much the same?  Not just in our sexual desires, but in our needs and vulnerabilities as well?  You wouldn’t think this was a horrifically shocking message to convey to society–but it is. It still is.

This is why a cross-dresser’s sexuality is still upsetting to so many people.

Would you ever be tempted by a cross-dressing hottie? We know that men who like to cross dress aren’t always gay.  But what about seducing a smoldering gay guy out of his garter belt and back into our camp for just one night? Would you ever?

Meanwhile, follow your naughty desires and follow our blog.  We’ll even let you try on our high heels if you want.

PS: Happy Halloween.  In the mood for other good campy Halloweenie blog posts? Say no more:

I’m a Monster, A MONSTER! 

Horror Sex Camp

Hunks O Steel: Cybogs, Sexbots, & ‘Steins

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