Unrealized sexuality: gay transvestites
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My discovery that I can find gay guys who wear dresses erotically enticing was just a few years back. It was a big surprise. Rifling back in memory showed that I'd glanced at a couple of crossdressing guys appreciatively but without discerning sexual potential. The couple of guys who wanted to be "made" to wear girl's undergarments left me with the worst impression.
My wild surmise was a gift. There were more people I could love or at least make love to. In reality those prospects were thin. At least in Durham, NC, not a place for meeting happy gay transvestites.
The real gift was new self-insight into my sexuality. Sounds fatuously sententious doesn't it? Given my highly recursive thinking about my thinking about myself it was a real treat. A glimpse of a pretty crossdresser would ramify. Finally I modified queer with pansexual: everybody (with conventional caveats) is lovable, sexy.
My sexual satori led to lots of words. Mostly about myself but people I'd come to know, however virtually. And the sometimes painful ambiguity taking gender too seriously but sometimes stepping above it.
I was meeting guys through the web back then so I made my interest visible. That was habitual, have a sexual or emotional inclination: publish the fact. You can't beat the Internet for scattering little spider webs of desire and hope. To say that most gay men who wear dresses are skittish is putting it weakly: they are frightened. Aside from a few near meetings my personals directed to crossdressers came to nothing. Annoying and distressing but not a huge problem: they were only one of groups of people I was open to meeting.
Mostly because of drag queens and transvestites I met online they were often in my thoughts. Several thousand words about gay crossdressers later I've never written of them as simple objects of lust (well if you look hard there is one erotic story on this website). I haven't lain awake at night dreaming of them. Away from the web and keyboard transvestites don't come to my mind that often.
As part of my little series of sexual possibilities I'd have liked to have explored I thought I'd write about gay guys who wear women's clothes simply in terms of lustful fantasies.
If I could build a male girlfriend to order what would he be like?
Once I had a vivid image of a pink-haired Japanese boy. This predates manga or anime finding an American audience. The Japanese boys in San Francisco that caught my eye were always shorter, demure looking even if they were probably thugs and the ones I liked looking at the best had tinted hair. A transitory fantasy I might not even remember if I hadn't written about it in an email to a friend. (Wondering why I say Japanese and not Asian: in SF there were lots of Japanese guys, I'd never heard of ladyboys. Can't really claim an ability to distinguish Sino-Asian features.)
My made to order girl boyfriend would be a living pin-up parade. He'd offer the pleasure of variety, forever playing with his appearance, shifting through a huge slice of feminine typology. Imagine a guy who is a living Olivia catalog. I like the idea of his trying to please and challenge me with his changes in makeup and dress. My fantasy gay crossdressing guy would be ever changing eye candy.
His personality would span the bitch to the demure. Sexually he would be yielding, submissive, a slut. Honestly that isn't how I'd have originally framed things. But there seems to be a strong correlation between transgendered sexuality and submissiveness and masochism. More expressions of being on the knees that sitting on a man's lap.
My ideal gay girlboy would know that he could be sexy simply in a t-shirt, jeans and a little makeup). Crossdressing doesn't have to be only in the externals: gender qualities can be manipulated with movement, mind and voice. That kind of confident androgyny is rare.
As is my ever managing to write an entry about simple lust.
My very long essay Gay transvestites (learning to appreciate their beauty)
(This is part of an informal series that started with leathersex and hopefully has only two more installments.)