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.)


“…..seems to be a strong correlation between transgendered sexuality and submissiveness and masochism. More expressions of being on the knees that sitting on a manís lap.

My ideal gay girlboy would know that he could be sexy simply in a t-shirt, jeans and a little makeup). Crossdressing doesnít have to be only in the externals:…..”

Dear Richard, Sir, You are so observant, and Your description of the typical androgynous boy is so accurate. i have often wondered why my own sexuality is so very different from the average gay guy that i know. i rarely dress in “women’s clothes” per se, although just about 100% of my casual wardrobe now comes from the women’s departments.. mainly, as you say, flared jeans, tight tops, and a “little make-up”. And with that also comes this incredible need to be submissive and enjoy pain. i can’t really explain it, but it is a different “gayness” than most of the “straight” gays that i know. And yes, i think the sight of a feminine boy, cross-dressed, or dressed androgynously, is a very alluring one…….


The way you dress is actually what I find sexiest. Because it really is androgynous.

I?m pretty sure that you know I have no problems with submissiveness or masochism. It is just that feminine males of all flavors seem to share those needs. Not that I?d ever argue with anyone?s sexuality.

Take care.

Thank you for taking time to share your thoughts on gay crossdressers. Although I am more transgendered, I don’t yet live full time as female, and find it difficult (I live in Des Moines, Iowa)to find a man to date who finds both my sides attractive. It’s nice to know there are those out there who find us attractive

Best Wishes,

Maria Bryant

That entry was just addressing a specific kind of person. One of the reasons that I call myself ‘pansexual’ is that I think all trans(vestite)(sexual)(gendered) people are lovable and attractive.

i really enjoy your writing on the subject. perhaps it’s because such desires are usually kept under wraps. but thank you for being up front about it. i am just starting to discover women that are interested in t-girls, which is cool, since i prefer women, but i have to applaud anyone who is honest about their attractions. its refreshing. thank you.

I am a transvestite & wish to have my breast enlarged. I am currenty an A/B cup. I also live in the Memphis Tennesee area. I would like to meet a nice gentleman who would treat me nice.I am a virgin.

Faith you’d be better off looking on some place like URNotAlone.com - wish you the best of luck.

The very first time I actually met a real transgendered female, I really didn’t know what I should be, angry, no I was just very very confused. I spent the day with my new friend. You know right after we parted ways I felt so guilty like I committed this sin. Am I now real queer I asked myself? This memory is like it just happened to me today and it happened almost 30 years ago. I went home and jumped in the shower and thought that this would cleanse me of what I had done. I often wonder if any other people had the same kind of problems. If so feel free and drop me a line. I’d love to hear from you.

My first time was with a work friend . He rang me for a chat.I knew he was bi.and I was curoius.I had been crossdressing a while and I thought why not take the risk.I met him at the door dressed enfemme.He was not surprised.He had read me.needless to say he left with a smile on his face.

I think a lot more crossdressers are gay or (at least bi) than like to admit it.

I enjoy making love to my wife whilst fully en femme but the pleasure of doing it with a guy, who I feel enjoys it and doesn’t just go along with it to please me like I feel my wife does, is all the more acute & satisfying.

the more effort I put into dressing up (full makeup etc) the more I desire male company in preference to female

I had plenty of offers for ‘discreet’ fun (e.g., behind their wife’s back) from supposedly heterosexual crossdressers when I spent time online meeting people.

And the crossdressers would have been actively seeking out contacts in a site categorised under gay- otherwise they would be cruising online chatrooms under the heterosexual “men who want to meet women” category and would make little or no reference to their cross dressing tendencies.

Speaking from personal experience (a security guard at work who I didnt know was in the building & who interrupted me when I was trying on a particularly ruffled blouse/flouncy skirt I’d bought in my lunch hour) there are also more straight guys out there (than would like to admit it) that, given the opportunity, they can’t wait to lift up the skirt of an obvious guy in drag and perform oral sex - maybe its the skirt that makes it acceptable in their own eyes - it certainly did with him.

interesting thread, As a life long 40yr old transvestite i can say i have hardly had any cross over with the gay community. I dont really find i can identify with gay men. To me the term ‘gay’ is really a cultural word and it is a culture which is completely alien to me. It must be said also that gay men find it very difficult to identify with transvestites too. I am very comfortable though to identify myself as a homosexual transvestite…go figure. I am now in my first real relationship with a ‘gay’ man. ~I think this only came about because i knew him from work rather than the usual way of meets off the net or clubs. we both have had a little adjusting to do i think, but now i am very happy to be considered his gay wife, and so lomg as it is obvious that i am the femme of the relationship, i dont ALWAYS feel the need to wear a dress to feel right…though it does help

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Pansexual Sodomite
Ambiguously Gendered , Love and Lust
Unrealized sexuality: gay transvestites
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