The Male Hustler Read online

  “So in that respect I hated my genitals, I felt they were male organs attached to a basically female body. But at the same time, they were what I got my kicks with. I would come by ejaculating through my penis, and the idea of cutting that off, of removing that pleasure part of the body—well, it was a conflict. I never did go to Denmark but I never entirely stopped thinking about it.

  “I could never go that route now because of things I have learned about myself. I know that I am a woman in certain very important respects, but I also know and am able to accept that I am a man in other respects, and an operation would take something away without giving me anything in return. If you’re familiar with the operation, you know that they build in an artificial vagina. They create folds in your flesh surgically. If that’s a real vagina, then you can get milk from a bull’s tits. I mean, love, it’s nonsense. A woman is more than something with a hole to stuff a cock into. A woman is ovaries and tubes and a uterus and all sorts of subtle plumbing which no doctor can install in a male body. Oh, for heaven’s sake, a clitoris is the female version of the penis, right? So a transsexual who has his cock removed is brilliantly turning himself into a woman without a clit. There are so many ways in which the whole thing doesn’t make sense. You give up your manhood without getting womanhood in return, and you turn into, I hate to say this because I’ve known transsexuals and hate to put them down, but you turn into a nothing! Neither fish nor fowl. Nothing!

  “A perfectly straight man, straight in the sense that he could not under any circumstances have sexual relations with any sort of male, is never comfortable with a transsexual unless she keeps the whole thing a secret from him. And a gay male is usually put off by a transsexual. He will usually think of her as some sort of freak, someone with something missing. So what does a TS do? Either you move to a new town and hide your past completely, or you see your old friends and find out that they have trouble relating to you. I know that fucking operation is popular now, and I know it’s getting increasingly more popular every year, but I’ll make a prediction—I’d be willing to bet that in another generation it will hardly ever be performed. Because as sexual liberation gets more and more widespread and as more and more people are able to accept abnormal aspects of themselves, the lines between the sexes are going to blur far more than they already have. And a person like me is going to feel far more comfortable being himself or herself—if you prefer?—than trying to conform surgically to the old idea of two firmly delineated sexes.

  “I was talking to a fellow the other day, a man I would characterize as very square but very open-minded. And he asked me, ‘Well, what are you? How would you categorize yourself?’ There was a time when I really objected to that question.

  “So this time I said, ‘I’m a woman with a penis and testicles.’ He wanted to know what I meant, so I just repeated what I had said.

  “‘But a woman can’t have a penis and testicles.’

  “‘Why not?’

  “Well, he was really confused. ‘Look, sweet,’ I said, ‘you can think of me as a man with female features, and a female personality. Or you can think of me as a woman with male sex organs. Or you can cut through this bullshit about labels and just think of me as me, Brendan or Brenda, whichever comes easier to you. You think of yourself as completely straight and you respond to the femaleness of me, but if all you want is a genuine woman you don’t have to see me. Would you like me better if I didn’t have a cock? Think about it.’

  “This was a fairly heavy speech to lay on this particular person. I’m sure he’ll be working it through his mind for a long time, and he may not be delighted with what he comes up with. The point is that I wouldn’t like me better without a penis, and, even more to the point, I’ve come to like myself a lot better than I once did. I went through a long period of shame and another long period of anxiety about my identity, and now I’m largely past that. Oh, I get depressed, and I find any number of things about myself I’m not thrilled with, but generally speaking I feel pretty comfortable being me. And I don’t know of anything more important than that. Life is a bitch no matter what, and if you don’t like yourself it’s a disaster.”

  • • •

  Brendan is twenty-two, short and small-boned, with chestnut hair and haunting brown eyes. The first time I met him I had not the slightest idea that he was anything other than the singularly beautiful young woman he appeared to be. Our meeting was arranged by a homosexual acquaintance who thought I might enjoy interviewing a “fag hag”—i.e., an ostensibly heterosexual woman who prefers the company of male homosexuals. I was thus introduced to “Brenda” and chatted with him and my friend over drinks.

  In the course of this elaborate charade, “Brenda” gave me the full treatment—long-drink looks with those extraordinary eyes, little vocal tricks in a rich contralto, suggestive flicking of tongue over lips, and the intermittent pressure of “her” knee against mine under the table.

  I must admit that there was nothing equivocal about my reaction to Brenda. I was very strongly attracted to her, responded to all her flirting, and wanted nothing more than to send my gay friend on his way and take this beautiful young thing home to bed. I did realize that this sort of flirtatiousness on the part of a fag hag is not uncommon, and is often accompanied by a total unwillingness to carry a relationship any further than flirting. But Brenda’s coquetry seemed so unqualified, so genuine, that I could not believe she did not intend to see the game through to its proper conclusion.

  After all of this had gone on for awhile, my friend excused himself and went to the men’s room. I took Brenda’s hand in mine and suggested we might have dinner together.

  “Just the two of us?”

  I admitted that was what I had in mind.

  “Oh, dear,” she purred. “Whoever knows where that sort of thing might lead?”

  I suggested it might be interesting to find out.

  “It might,” she said mysteriously, “be rather more interesting than you suspect.”

  When my friend returned, Brenda and I were still holding hands. The two of them exchanged cryptic glances and began to laugh. I wondered aloud what was so funny.

  “Jack,” my friend said, “we had better get you another drink, because I am about to blow your mind.”

  He refused to explain until the drink came. I went on holding Brenda’s hand and used my free hand to take a sip of my drink.

  “Brenda,” my friend said, “is a boy.”

  I didn’t get it. He repeated it, and I asked if he meant that she was a lesbian.

  “A male in drag,” my friend said.

  “I have a cock,” Brenda(n) said.

  • • •

  This anecdote—one, incidentally, of which I am not particularly proud—is reported in detail because I can think of no better way to stress how deceptively female Brendan is in appearance and attitude. I cannot recall ever having been quite so completely astonished by anything that has happened to me. The series of mental changes I went through on the heels of this revelation is almost impossible to recount. I had never previously felt sexually attracted to a male and had never considered having relations with another male, and now a person who had attracted me as strongly as anyone had ever done was suddenly revealed as a male. And I was still sitting there like an idiot with his or her hand in mine.

  There was a bad moment there. Brendan’s face took on an expression of alarm at the possibility that I might grow suddenly violent. (This, I learned later, had occasionally happened at somewhat more intimate moments of revelation.) I, for my part, was struck momentarily dumb. And then the three of us simultaneously erupted in laughter, hysterical laughter that dissolved the tension quite completely.

  “I couldn’t resist it,” my friend told me, after the hilarity had settled down. “I felt Brendan would be a perfect person for you to interview. He’s the most convincing transvestite I’ve ever met. So many teevees look like parodies of girls, and he looks like the genuine article. I mean, it’s not
all clothes and makeup. He can wear male clothing and come on like a girl. And he’s bright and self-aware, and you were bitching that so many interview subjects are shallow and inarticulate.”

  “And I’d just love to have you interview me,” Brendan murmured, doing the full number with the eyes again.

  “And you figured it would be an unparalleled put-on,” I said.

  “Not only that. I felt the only way you could get Brendan’s full impact was this way. If you knew in advance that he was a male, you would have to approach him with preconceptions. I had only your best interests at heart, Jack.”

  “Oh, I’m sure you did.”

  My friend grinned. “And I must admit I wouldn’t have missed this scene for the world. I’ve got a good streak of bitch in me, you know. And it delights me that you’ll be wondering about yourself for a good long while after this. Are you as straight as you thought you were? Is there such a thing as straight? After all, a person who writes books on sex ought to contend with questions of that sort.”

  “You’re a real prince,” I said, approximately.

  “I’ll take that as a compliment, Jack. Actually I think I played quite fair. Suppose I never said anything, just excused myself and vanished? Suppose you took this luscious little number to dinner? And suppose she went right on being Brenda, and you didn’t get to the moment of truth until the two of you were in bed?

  “Christ,” I said.

  “Must run,” said my friend. (Friend?) “Have fun, boys and girls. Have a pleasant interview. And Jack, you should enjoy pretending that she doesn’t turn you on any more now that you know the awful truth . . .”

  Later Brendan told me that my friend had originally wanted to let me make the discovery in bed. “But I told him absolutely no. I’m not the masochistic type. I don’t enjoy having some uptight latent beat the living shit out of me because he doesn’t want to face uncertain things about himself. I had that happen once, and the stories I’ve heard. You can imagine. But I like running the number we did today. Attracting a man, getting him to commit himself, and then letting the cock out of the bag, so to speak.”

  “What usually happens?”

  “Shock. Disbelief. More shock. A lot of the time we wind up laughing, like today. It’s a great way to deal with something that’s hard to handle.” A significant pause. “You’d be surprised how often a man who never went that route before will decide that my cock is no reason to stop wanting to get me in bed.”

  The full treatment with the eyes again. A soft, knowing smile.

  “Interested?”

  • • •

  “I had a childhood that was so classic it seems positively banal. Mother was a repressed mouse of a girl who managed to preserve her maidenhead for almost thirty years, perhaps because nobody was interested enough to contend with all that shyness and churchiness. This was in a little town in Schoharie County in upstate New York. The only county in the state with less population now than during the Civil War, so you can imagine what a swinging cosmopolitan place it is.

  “Then someone seduced the poor woman, evidently with a promise of marriage, and left town around the time that she began not having periods. God knows who he may have been. A proverbial traveling salesman, I suspect. I grew up thinking my father had died in the war, then learned by accident more or less what had happened. I spent a long time wondering about my father, who he was, if he’s still alive, all of that. The standard fixation on the unknown father, the standard love-hate thing. Like he’s a bastard for having left me, but also he’s out there somewhere, the father who will take care of me and make me a whole and secure person. I think I’ve largely outgrown that bullshit by now.

  “Except that I still find myself wondering if I might ever have made it with him, without either of us knowing who the other one was. Of course I’ve always been promiscuous, and I went through a stage shortly after I came to New York where I really played the numbers game. I had to prove to myself that I was attractive, and I wanted quantitative proof. I’ve serviced as many as thirty men in a night. Forgive the crudeness, but sucking doesn’t really tire one out, you know, and you can just go on as long as you want. So it’s not inconceivable that one of the men I balled at one time or another was my long-lost Papa.

  “Pointless to brood about it. Or to go on Freudian trips about how my whole sex life represents a search for my father and an attempt to possess him sexually. That kind of thing is worth considering but not worth dwelling on forever . . .

  “After she was pregnant and deserted, my mother moved in with my Aunt Alma. Alma was her older sister, a good dozen years older and a childless widow. It surprises me that she ever got married in the first place. I never met a woman who had less use for men. It wasn’t so much that she hated them as that she was totally incapable of relating to them. I’m sure she was fundamentally a dyke, but that her orientation was such that the possibility of female homosexuality never once occurred to her. She would have the inclinations but would never recognize them, never even suspect them.

  “That was the house I grew up in. Huge old house in this dying town with these two cloistered sexless ladies. Alma absolutely dominated Mother, treated her more like a child than a sibling. And mother learned her lesson, never looked at another man. I think she would have grown her hymen back if she could have found a way.

  “Classic faggot background, isn’t it? I had the whole bit, played with dolls, was coddled, all of that. And I was physically right for the part. Small and dainty and neat and all the rest of it. It wasn’t a bad time, you must understand. I enjoyed childhood. It only becomes unpleasant in retrospect.

  “I’m not sure when I first realized that I was different. That I was a boy who was not like other boys. It sometimes seems as though it was something I always knew . . .

  “My first sexual experience came when I was twelve years old. At this stage I had not yet learned how to masturbate. Although there was a thing I had started doing. I would lie in bed at night and stroke my body, sometimes with my hand but more often with a piece of fur or a silk stocking. But I didn’t concentrate on my genitals. I would just stroke myself all over. I didn’t identify this as a sexual thing at the time, nor did I have orgasm. I just liked the feeling of it and the whole process made me feel, oh, admirable, attractive.

  “I was in seventh grade. For the past few years other kids had made fun of me, called me Brenda, that sort of thing. Imitated me. As best as I can remember, I didn’t hate this as much as you would expect. There was something about the teasing that I enjoyed. I think it must have made me feel important. And I don’t think it bothered me that I didn’t have friends. I felt so different from everyone, from both the boys and the girls, that it must have seemed logical to me that I would be alone most of the time.

  “I was on my way home from school one afternoon and these two high school boys, I suppose they were fifteen or sixteen, started walking along with me and talking about me. ‘Isn’t it cute? Is it a boy or a girl?’ Obviously I wasn’t cross-dressing or making up, but I was naturally effeminate in behavior and, hell, I looked like a girl. ‘What’s your name, sweetie?’ They knew my name, but I said it was Brendan, and of course they called me Brenda.

  “I was excited that they were paying attention to me.

  “Then one of them told the other that they could have some fun with me, that I was the same thing as a girl. I was totally ignorant about sex at the time, just incredibly ignorant. But I was wildly excited without knowing what I was excited about. They asked me to come for a walk with them and I did. We walked on out of town and they went on teasing me and talking about blow jobs, which was an expression I had heard, but didn’t begin to understand.

  “We wound up in a wooded area on the edge of town. They told me to take my clothes off and I refused. If I knew nothing else, I knew nudity was taboo. They forced me. I put up a token struggle, but, actually I was thrilled to the core and enjoyed being forced this way. That element of masochism, incidentally, has l
ong since vanished. I like a man to be masculine but I don’t enjoy being overpowered. As a matter of fact, it’s very important to me that I be the one who does the seducing . . .

  “They made a big thing about my penis. ‘Look, he’s got one after all! I guess he’s a boy after all! But it’s so small it hardly counts.’ That kind of thing. Of course it was small, I was twelve years old and undeveloped and hairless. It’s grown somewhat since then, lover, in case you were wondering.

  “They dropped their pants and I blew them. Sucked them off. They had obviously experienced this before; though whether it was with girls or other boys or even with each other I have no idea. I didn’t like the act itself. There was an odor that disturbed me, perhaps because I associated it with uncleanliness. I had always been scrupulously clean, fastidious. But I was enormously impressed with the size of their cocks. The only cock I was familiar with was my own, and it was a puny thing in comparison. For the longest time afterward I thought that the relative size of my cock was an indication of my femaleness, that because I had a tiny one I was halfway between being a boy and a girl.

  “The ejaculation surprised the hell out of me. I gather a lot of people throw up the first time. I didn’t, but kept spitting, and when I got home I must have brushed my teeth and gargled for hours on end. Ah, how tastes change!

  “Afterward, they asked me if I knew how to jerk off, and I again didn’t know what they meant, although again I had heard the expression. One of them played with my balls and said he didn’t think there was enough there to work with, and then he began playing with my penis and wonder of wonders, it got hard. Still tiny, but hard, and what an exciting sensation! I had the first orgasm of my young life. The one who did it told the other one that I was fun to play with, and the second one tried it, but I couldn’t get aroused a second time. They wanted to do other things, I don’t remember what, but I said I had to get home, and home I went. Later that night I jerked myself off with a piece of fur and thought about being a girl and imagined having a huge stiff cock in my mouth.”