J Wells - The Male Hustler

“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.”