Learning to appreciate gay guys who wear dresses*
As I type this I see someone is searching Google for “self sucking gay crossdressers.” Some sex fantasies can still surprise.
One nifty aspect of writing about yourself is the quickening of memory.Reviving memories almost forgotten.
In 1972 I’d left home and Ebba and Gordon were my roommates. Victor had left John for Nancy and John moved to Atlanta. With fatal foolishness I fell in love with him and moved into our own apartment;; slummy complex on Peachtree across from Piedmont park. The man below us was a Sterno addict and would keep us awake but in stitches mooing like a despairing cow.
Glenn, our building superintendent was an ignorant middle-aged man. He was trying or at least hoping to transition from genetic male to medically created woman.
Christine Jorgensen, the inspiration for Ed Wood’s Glen or Glenda, had undergone her gender transformation twenty years earlier. Her fame survived after a fashion so I’d heard of sex change operations. I think Glenn may have been taking hormones. He was often bed-ridden and so raffish I can’t remember if he went en femme. I didn’t think much about it except for a small doubt: was he sincere or just wanting attention.
Back when I’d been living with Gordon and Ebba I made my second abortive attempt to have sex (having someone’s roommate throw ice water on you through the bedroom door can’t help but spoil the mood). Thinking back the young little ice queen I’d climbed into bed with had on some kind of silken women’s undergarment. It would’ve been mentally if not tactilely invisible to me back then. I hated wearing underwear. Pleasure in wearing a woman’s undergarment wasn’t something I’d hear of for many years..
Bobbie, the ice queen’s roommate excited me strongly. A gentle, sweet guy very much in love with his hustler boyfriend. Bobbie was a naïve Southern boy with the special kind of face that can make a pimple into a beauty mark. Maybe if I’d understood the fragility and inevitable failure of such an entanglement I’d have made a pass at him, I dearly wanted to. Boys like Bobbie were always fiercely faithful (their boyfriends never were). Much later I saw Bobbie on the street dressed as a woman. First time I – knowingly at least – saw a passable transvestite. With wig and make-up he wasn’t a bit less appealing and lovable. My first site of a pretty drag queen, I’d have loved to have the boy under me even in a dress but only in recollection would I see that. Didn’t matter he’d donned drag to go hooking.
androgynous/masculine seeks androgynous/feminine
From my first personal ad appearing outside of The Atlanta Barb the gay newspaper that I helped run. Marc (aka Rose C’est La Vie) was the only person to answer. Marc sometimes wore dresses without makeup or in anyway trying to assume the persona of a woman. He looked fetching in a dress sans makeup, wig, or jewelry. A minor sort of queer political statement: genderfuck. Never gave his appeal in a dress a second thought. I called him and we laughed when told him that the ad was mine. Years later when I was living with Siobhanand visiting Atlanta, Marc and I got to know each other little bit better just before I left Atlanta after a visit. The laughter years earlier might’ve been a mistake.
If the word androgynous hadn’t appeared in the ad I don’t know if I’d remember it. Years later it would surprise me to discover I’d employed it in the first half of the 70s. A preference for a limp wrist aside it was probably that David Bowie’s early days had popularized it. The wild eyed boy from Freecloud then seemed the summa of androgynous male beauty.
Callow hermaphrodite fantasies
While I’d placed a couple of personals, I’d never responded to one until I was living in San Francisco. Off and on again I’d had fantasies of making love to a hermaphrodite. (I hope any pre-operative MTF transsexuals (or intersexuals persons) who see this will forgive me. Your struggles and pains, the misery with one’s biological lot, were unknown to me.) My fantasy image was inspired by the classical myth of Hermaphroditus the child of Hermes and Aphrodite. Honestly, yes it was a chick with a dick, a shemale – did that nomenclature exist back then? My dream boygirls were fuzzy conceptions, no suspicion that they actually existed.
What the ad said I don’t remember. “Pre-op transsexual” wouldn’t have meant much to me back then. Maybe she spelled it out: I have tits and a cock. The voice on the other end was creepy, bitter. She required a ‘donation.’ Back then there wasn’t much public help for men wanting to have the bodies of women. That the monetary burden has driven some mtf transsexuals into prostitution I didn’t know.
Back when I was selling callboys I’d intended to eventually pay for sex: half as a lark, half for a quirky sort of self-edification. Many youthful ambitions are never realized; I never did buy a boy even though by twenty-one I knew many male hustlers. Perhaps if the voice had been kinder or vulnerable, vulnerability has always had the power seduce me, I’d have happily made a donation. I can’t fault her. She probably heard from many self-proclaimed real men whose most tender line was that they’d show her what it was like to be a real woman. After the phone call I dropped the idea.
Here’s the kicker: I never connected my admiration for Bobbie or Rose, my call to the pre-op transsexual with my sexuality. I thought of myself as a gay man who only wanted other gay guys. Even when I lived with a woman for five years my sense of myself as gay never wavered. In my coming out story I noted my inner blindness. My eyes liked what they’d seen, my heart stayed shut.
Many years pass.
Have you ever been to alt.com? It is the match.com of BDSM personal ads, although the graveyard of online personals may be more apt. Personal ads are often a tentative gesture toward assuaging an unmet need or suppressed desire. The more atypical the itch the greater the likelihood of a retreat back to self-denial.
Browsing the listings of North Carolina submissives I ran across a photo of a crossdresser: nude except for hosiery, bent over showing his/her butt (I love buttocks, male or female). My body responded much to my surprise. Fashion photos of pretty boys in sweaters, Renaissance paintings of pageboys were my usual idea of erotica.
I like nudity as well as the next human being. OK, maybe not. Naked pictures are fine but I rarely see any that make me smile with delight. Vapid faces bereft of individuality. Without a hint of irony, prankishness, kindness I can’t perform my viewer’s role of investing the photo with sexual glamour. When I made myself healthy and my sexuality reemerged I tried to take advantage of the Internet’s vast erotica archives. (Aggravated my carpal tunnel to no purpose.) Playgirl centerfolds on their motorboats and motorbikes weren’t for me.
Also on alt.com, I saw a facial shot of a very gentle looking longhaired guy. His listing said he was transgendered male in the process of becoming a female. His words matched the vulnerability of his picture.
I made a small evolution. The gradations between male and female became alive, as full of erotic joy as the favored two. I found that the people in between and outside were just as lovely, just as lovable.
As a young gay man to me guys in dresses meant drag queens in bars. Back then, lip synching pop songs they looked like tacky mannequins that had melted under the sun. Their strenuous, aggressive personalities are probably necessary in their world (and dealing with the rest of the world). A little bitchiness is appealing but I don’t like being near loud, pushy people.
That was the early 70s. I hope their lot has since improved but back then even in the bars they perform in they were regarded by many as little more than grotesque oddities. Many of them lived in poverty with hustler boyfriends who were more likely to rip them off than kiss them. Some had regular jobs where they carefully concealed their weekends (like most gay men).
A new color of sex discovered I went exploring. It being the 90s I went online.
Inevitably I discovered the vastness of my ignorance. Most transvestites are straight, many married. Lucky ones even have wives who understand and support them. I ran into them on Usenet when first trying to learn about crossdressers. Finding out that I am gay, they were as intolerant as any other group and told me to find a drag queen in a bar.
I quickly narrowed my conversations to gay crossdressers. Do you think you have a hard life, that people don’t understand you, that you’re an outsider? Try life as a guy whose deepest satisfaction is wearing women’s clothing. The average gay man – who damn well should know better – can’t be expected to regard you any more kindly than the straight punk.
Invisible at the most horrific extreme are the guys who’ve never let themselves put on as much as a garter belt. Many of them want a man to force them to shave their pubic hair or mildly feminize them in other was (I remember the young jocks who wanted me to ‘make’ them shave their pubic hair). Others dress up at home their mirror their only companion. Thanks to the web transvestites can meet other transvestites. A few post photos of themselves anonymously, appearing en femme publicly with little risk.
In the Yahoo clubs and gay.com chat rooms crossdressers try to hookup with guys. Flirting that rarely leads to a meeting; true of most online flirting, least likely for them. Some are afraid of being beaten. Most are afraid they’ll be found unattractive and laughed at. The saddest minority covets the attentions of self-proclaimed heterosexual men, swine that can’t admit to themselves that a guy in a dress fulfills an appetite that a genetic female cannot. (At the risk of sounding defensive: that isn’t why I find crossdressers appealing. At the simplest level they are just part of a spectrum. If they are happy to accept themselves as a gay male even if playfully aping the rules then I can happily place them on a romantic pedestal. Sadly, they are rare.)
The bulk of the men trying to date transvestites mostly boast that they are real men and talking about the magnificence of their penis. Ashamed of their sexuality, unable to admit they are attracted to men. Interestingly they seem most fascinated with the transvestite’s phallus. Meeting one of them is apt to be as romantic as a prison gang rape.
And there is the terrible division between those who can pass as a woman and those who can’t. The latter often despise themselves for their imagined failure. Akin to people who feel themselves ugly but perhaps with more self-hate.
When I was on Yahoo daily I got messages from guys who wanted to meet me (99.6% of which to which I said no). The first transvestite who asked to meet me was a (I thought too young) guy of 25 who I was able to discern lived near me. He was skittish boy, who I felt needed to be able to talk with someone more than sex. Thinking a public place would give him security I suggested we meet at a nearby mall. He was so scared I suspected he’d never shown up. I emailed him the day before we were to meet. He never replied so I didn’t bother going. A public meeting may have been more intimidating than a less safe one in private.
A really smart transvestite emailed me for a date. His confession that he wasn’t passable didn’t’ deter me. I asked my (straight) friends to which restaurants I could take a transvestite without fear of harassment. Wellspring Grocery was my usual place for meeting possible dates from online. Over coffee I discovered he wanted to go to Legends a Raleigh drag bar. Bars bore the fuck out of me; I haven’t been to a bar since I left San Francisco. I assented but he could tell that I didn’t warm to the idea. We never met again. He’d thrown me in an odd way: he said the “man proposes and the girl disposes.” Femininity isn’t passivity, in an erotic context you can tell me where I’ll be and I’ll be there. A weakness for (even the sweetest) Bitch Goddess. Reflecting I’d say my reaction was ignorant. Role play is part of the experience.
A tall, super-slender crossdressing young cop I came very close to meeting. A gruesome series of crimes intervened. Bright and self-aware my interest was very strong. (Even if I have a phobia of police.)
The one I wish hadn’t gotten away: young, soft, tender, he wanted me to pet him and hold him in my arms for a long time before the ‘horizontal boogie’ as he called it. Pretty without any cosmetics, having his own long hair we made an assignment. Crime (not any that he had to investigate) again intervened.
Charles, who wears men’s clothing only (except for the heels he sometimes puts on) arrived and I told both never mind. Both were pissed.(As were a couple of guys who didn’t crossdress. In choosing Charles I implicitly slapped them in the face with rejection.)
Intentionally neglected are the locals wanted ‘motel room fun.’ Many of those were married. I’m a fairly amoral person but have never been up for adultery.
Why all the fuss about crossdressers
Folks who’ve seen my many entries on crossdressers may be surprised that I’ve never had much in the way of crossdresser fantasies. Crossdressers became a romantic possibility, not an obsession. I’ve always loved girlish gay guys. I’d latterly accepted that they might wear skirts and stockings.
Crossdressers are special to me in a couple of ways. Many of guys I’ve loved were picked on at school or had “Freak!” or “Faggot!” shouted at them from cars. My erotic tenderness has been dangerously reinforced with a hope to protect and uplift them. Crossdressers are outsiders even among gay males; they live more deeply with the outsiderness that still lingeringly colors queer life. Transgressive is a word that I’m tired of it but crossdressing is more transgressive than merely being gay. (When I was online more I’d get slammed for caring about them. Why would I be interested in an embarrassing freak when real men were to be had? I grew up with a violently ‘real’ man Even if you, like Big Mack, can bend bolts in your hand and pick up the back of a 1960’s care, you aren’t going to warm my heart. And there were the inevitable hasty readers who thought I was a crossdresser.)
Differently but maybe more importantly: my evolution either occasioned or coincided with much self-discovery. A new source of self-insight is more exciting than, say, a new fuck. My weblog is about nothing if not my own self-absorbed self-exploration.
Not that discovery of new erotic possibilities didn’t enrich my daydreams.** But come the dawn, come reality.
For me crossdressers inspired notions of playing with, teasing, toying with, ultimately transcending gender. The woman that I lived with never shaved her legs, wore a dress of carried a purse. Many male crossdressers want to be a woman in an icky way.
That crossdressers wanted to emulate bourgeois values shouldn’t have surprised me. Clothing aside they are just like the other happy Wal-Mart shoppers and Big Mac eaters.
Many of them wanted to be female in a dated housewifely way. I never wanted to live with Donna Reed or June Cleaver. Role-play can be fun but not taking it in dead earnest. Aesthetically the bad wigs and impossible clothing put me off. Bourgeois garments alienate me regardless of the frame beneath.
A big slice of them wanted to be dominated, overpowered, humiliated. BDSM is OK but the consistency was appalling. Few genetic women want to be told to “Get down on your knees, bitch!” or slapped in the face. I’d flattered myself with feminist insight but the gender stereotyping implied by this was a real revelation. I wrote a story to help me explore the idea of satisfying a submissive crossdresser.) In an odd way they mirror the surprising male sexism to be found in heterosexual male submissives. (That I was looking at listings of submissives on alt.com but cavil at some of their motivation isn’t as contradictory as it might seem. Pleasure in submission and pain is fine, self-hate isn’t.)
Simply put I like crossdressers who even if wish they could spend every hour en femme don’t hate being a male. Maybe they would’ve been born a girl if they’d had the choice. But they can accept being of both worlds.
The person above possesses clarity, elegance, individuality, competence and compassion . Because of his joy in wearing clothing not designed for males he’s mocked, he might even be beaten. Because of his rare quality, his nobility, if you will, even though crossdressers have never been an important part of my personal life I’ll always try to remember their status. I’ve always sent transvestites to his web site.
Dressing sexily & drably.
** I’ve segregated this part fearing that it will hurt or anger some crossdressers. This is a sifting of my tastes, not a manifesto on crossdresser fashion.
Pouting, yet sure of himself, the womanly curve of his back. Girlish and boyish in equal measure his image was part of my growth towards an appreciation of transvestites. (And if the copyright holder would email me I’ll remove the image or provide a link to your website which appeared to be dead.)
I’m susceptible to plenty of erotic clichés. (I’ve often wondered where they come from, having nothing from my youth to relate them to: probably fetish by osmosis.) Typical tawdry fantasy: a boy dressed like a girl hooker in hot pants. Less tritely: a guy who could use makeup to look like a girl in t-shirt (or halter top) and jeans: just a casual boygirl relaxing. The last is the imaginary crossdresser I can most easily imagine being with.
That I found this picture strongly appealing startled me. Momentarily I felt like a pervert. Really it is a very lovable image.
I’ve seen pleasing images of crossdressers in long stockings, short skits, Dresses? Sure. But a dress that looks comfortable, something you can relax in. Fancy dresses can be appealing but they are hard to pull of even if you were born with tits. Office worker’s drag, heavily constructed gowns – well I wouldn’t warm to those on a woman, nor you. Humor, strong stylizations are erotic; not emulating the commonplace.
Wigs are a problem. Good wigs are expensive. Some guys are lucky enough to be able to wear their hair long. Contemporary women do fine with short hair, it is a matter of styling. Old-fashioned whores and 60’s country music stars aren’t the best models.
Appropriate dress is a rare knack anyway. Probably if I were to go and look I’d find today’s crossdressers looking more like Pink than Martha Stewart.
* The safest phrase to use – finical quibbling over crossdresser vs. transvestite vs. drag queen merely wearies me. Drag queen is probably best left to the guy show perform in bars, the other two words seem merely matters of preference. I prefer crossdresser, transvestite – like homosexual – sounds like something in need of a cure.
NB: this is strictly about gay male crossdressers. Hetero crossdressers and MTF transsexuals are ignored for the sake of focus.
To quote the title of one of my Live Journal entries: Small town diva boy your mascara is smeared and I love you.
Richard Evans Lee, May 2003
Originally posted 2013-12-26 23:40:38.