Assuming the Position: A Memoir of Hustling

\ \ \ \ Chapter One\ \ \ The first time I worked as a prostitute, I went to Rounds, a bar on the East Side well known for its clientele of hustlers and johns. I had, at the time, a rather dubious motive aside from a real but customary need for money. My boyfriend, Tom, was leaving me, and I knew he had hustled in the past. I was in love with Tom and I wanted, I guess, to experience something intense that he had gone through, vaguely expecting that it would help me to understand him better and that it might even somehow bring us back together when he found out about it. I don't really know how I rationalized this at the time, and perhaps I just did it without justification, but hustling seemed like an extreme measure commensurate with the power of my passion for Tom. If he was going to leave me, I was going to become a hustler, saluting him, as it were, with a crude gesture I hoped he would recognize as desperate.\     I was nervous about the whole thing. I didn't know, to begin with, if I was attractive enough to get work. But once inside the bar I relaxed a little when I saw that there was an easy, erotic feel to the place and that I was about as young and good-looking as anyone else there. I was twenty-five. I was prepared for a room full of nineteen-year-old model types and gorgeously dangerous kids, but that is not what I found. There was a wide variety of hustlers at this famous bar—from young black boys up from Christopher Street to forty-year-old veterans with big dicks and enormous muscles. There were straight guys who made good money letting the queers suck them off, and there were prissy gay boys looking for"security." Some of the hustlers looked a little sweaty and rough, and I would have been glad to pay a few of them for the good fuck they appeared to promise if I'd had the money. Several times that night I was unsure about whether someone was buying or selling, and I didn't know how to respond to attention from a man five or six years older than me who seemed just to want free sex. I was also unclear about how to negotiate a deal; but I had another drink and watched for a while, and before long a deal had been made.\     George was an overweight and balding lawyer, but he looked clean and trustworthy, and he appeared to have taken quite a liking to me. I was flattered by his exclusive interest: he seemed to have found exactly what he wanted. About fifteen minutes and a martini later, when he suggested taking a taxi with him to Brooklyn and paying me $150 plus taxi fare back to Manhattan, I agreed.\     It was a long ride to George's apartment in a neighborhood the name of which I never knew. He lived in an enormous, ugly building with a depressing little fountain in front that was lit by scrawny colored lights. His apartment was furnished in a way I have come to associate generally with johns. The furniture is always about five or ten or fifteen years old—not new and not old. There is a large, low table in front of the sofa, usually made of glass or clear plastic or something painted white, upon which rest neat piles of magazines and a big glass ashtray. The whole apartment is carpeted, and there are full-length mirrors at several corners of the living room. The tall halogen lamps are brightly lit. The decor and mood feel a little forced, as if the man who lives in this organized place is determined to be comfortable there. The bedroom has more mirrors, and the bed is covered by an acrylic, floral-pattern blanket. The windows are never open; the room is air-conditioned all summer, which the man considers an indispensable luxury. The whole place is bleak in a completely ordinary way.\     And George, like many of my clients, had a dog, which he seemed a little embarrassed to talk to in my presence, as if he believed he usually talked to the dog rather too much.\     I was naturally ignorant about exactly how to behave on my first evening as a prostitute. I was prepared to be afraid of murder, rape, and satanic gang bangs, but George's building was so middle-class that I couldn't imagine anything happening there that a scream for help wouldn't bring to a quick and embarrassing end, and George seemed anything but dangerous. He turned out to have few expectations, and it was not at all difficult to make him happy. The very fact that he had hired a young man to come home with him was exciting for George, and I responded to his excitement. Before long I was standing up on his bed fucking his mouth, encouraging him madly. I surprised myself—though I didn't, I think, surprise George. He seemed prepared for everything that happened and ended up having what looked like a wholesome, cathartic orgasm. Afterward I made a point of lounging voluptuously on his brown velour sofa, sipping a Coca-Cola, making sure to give George his money's worth right up to the moment of walking out the door an hour after I'd arrived.\     He called a taxi for me, and when I left I suddenly felt very sad. I was feeling George's sadness—which for all I know he wasn't even feeling himself—in addition to my own. George's money was a lump in my pocket. I felt that I had reminded a lonely man of his loneliness and then left him to it. I thought George should not have done what he did and that I should not have taken advantage of his weakness.\     I was probably wrong to feel this way. In fact, George (who was a lawyer, after all) probably had no trouble paying my fee, and if he was lonely at midnight, at least he was less lonely at ten, when he'd been with me. He was capable, with me, of some sexy behavior that I suspect he found pretty impressive. George did not strike me as a person with a great deal of self-confidence, but he was surely suffering no lack of conviction when he was sucking my cock. At the time, though, I could only feel that what George and I had done together was depressing and disheartening, and on some level it was.\     Back in Manhattan I phoned Tom, the ex-boyfriend, from a pay phone, in tears, and told him about what I'd done. He reproached me brusquely and told me not to do it again, which compelled me to do it again the very next night. Over the next few weeks I committed myself to what was then, for me, a neurotic, sacrificial activity, trying to ease the hurt of having been abandoned by doing something I hoped would hurt Tom. I wanted to be scarred by experience and able thereby to show that my love for him was potent and real. I don't think my hustling hurt Tom much, and in any event we never got back together. I am still, in a way, in love with him, though I don't believe that is why I continued for so long to prostitute myself.\ \ \ * * *\ \ \ I remember Rounds, the bar, as a bizarre, somewhat wicked place. I liked it. I met all sorts of people there, including an older man who, according to rumor, hired every one of the hustlers that passed through the place and was equally passionate and demanding with all of them. He took me to a cheap hotel in the East Thirties where I remember not a word passed between him and the Asian man behind the fluorescent-lit counter; the little man just handed my client a key and we went up to a gloomy, windowless room with a bed in it. From the very beginning of the evening, this guy had been making me promise I would see him again the next day, and that I would allow him to "take care of me." I was to be his "nephew," and he would be my "uncle." I told him that I did not often have sex with my uncles, and he told me not to think about it like that. We won't be "having sex," he said, we'll just make each other feel good. Everything this man said to me, I believe, was a lie; his was my first encounter with the kind of prolific dissembling that often serves to lubricate and justify for himself a john's experience with a hustler. Most of the men who hired me, unlike George, the lawyer from Brooklyn, seemed unable or unwilling to accept the simplicity of having hired a young man to come over and have sex with them. It was as if that was not interesting enough for them—there had to be some psychodrama involved in addition to the sex for them to get their money's worth.\     Anyway, my "uncle" turned out to have some pretty energetic ideas about "making me feel good" and vice versa. His modus operandi, I learned later from another hustler at Rounds, was to seek out the most inexperienced hustler, coo to him about how good he will be to him and how much money he will give him over time, and then to get the boy into that dreary hotel and get as much sex out of him as he could for the least amount of money the kid would accept. Working out of the bar—unlike working for an agency, which I did later—there were no real rules, and negotiations were usually over a price and little more. Most clients expect no more than an hour of a hustler's time. But then most people are reasonable, and some just aren't. My "uncle" that night used what he worked up as our affection for each other—our fledgling friendship—to persuade me to stay with him long into the night. He was not at all reluctant to tell me how lonely he was, and how desperately he needed me to stay with him. He said he would give me money every day if l would be his "nephew." And then he would suck my dick again or ask for another "massage." I do not resent much of what I went through in my years as a hustler, but I am sorry that so early in my career I encountered the kind of emotional pleading this repellent man used to his advantage. He was a real nuisance, and I have never been able quite to forget the intensity of his undisciplined, unscrupulous need.\     I did occasionally pick up another hustler at Rounds for fun. Usually we would plan to meet at a bar downtown at about 2:00 A.M., after we'd both made some money. Then we would share some coke to wake ourselves up, have a couple of drinks, and go someplace to fuck. Sometimes one of us had more work than we expected and couldn't make the appointment at the bar on time, and, in any case, hustlers tend not to be punctual when they're not making money. It's a loose life, and the nights are long. Sex with other hustlers is best anyway when you're all getting paid for it. Some of the most picturesque sex I've ever had was on exhibition for paying customers. I remember one night at the Peninsula Hotel when a well-known restaurant owner had flown in his "friend" Chris from Los Angeles and hired me to join them. Chris was an Italian who loved nothing more than getting fucked by a hustler for hours, and the other guy liked nothing more than to watch. Since Chris happened to be very cute and about twenty-four years old, I was happy to oblige. The fact that we were being watched and paid only added to the excitement.\     After a couple of weeks I quit going to Rounds. I had a part-time job and did not really need the money (though I certainly enjoyed having it), and I found the bar monotonous after a while. It was in a neighborhood not easily got to from where I lived, and it was more fun to go downtown. I lost interest in hustling; it was too much work. And it did not appear to be making any difference in my defunct relationship with Tom, who was by then (and still is) living happily with somebody else. He cared about me, I believe, but he was not in love with me, and leaving me unequivocally was surely the right thing to do. Hustling out of the bar had been a way to distract myself from feeling hurt about Tom, because I could feel hurt by men more generally that way—hurt, in fact, it seemed, by the world, which was easier somehow than being hurt so intensely by Tom. If my life had led me to working as a hustler in a bar, okay; I could accept that kind of a tragedy because it was not, or did not seem to be, personal. It was a cultural tragedy.\     Rounds was eventually closed clown and became another old legend—people swear that Tom Cruise once bartended there. I had nothing to do with hustling for a while. I had my part-time job and I proofread books on the side, and I was close to finishing my undergraduate degree. I was writing reviews and a novel, and looking, a little heartbrokenly, for a new boyfriend. I had some good friends, thank god, and I liked my life.\     I finished the degree (in philosophy) and I finished the novel, and then I screwed up a proofreading job and couldn't get freelance work from Random House anymore. I found an agent for the novel, but she was unable to get it published. The idea of taking a full-time job was identical, for me, to admitting failure as a writer, which I was not prepared to do. I began to get a little hopeless. I didn't find a boyfriend—no one resisted me the way Tom had, and no one was, partly for that reason, as interesting.\     Disappointed by the meager rewards of hard work, I began to believe that hedonism was as good a philosophy as any, and better than most. If nothing matters, then why not have a good time while I can? I drank a lot and allowed myself to experiment more with drugs than I had before, and I had a great deal of sex with strangers, some of it unsafe. The hours I kept began to exclude, for the most part, daytime.\     I decided one day about a year after my last misadventure at Rounds to look into hustling again. I needed money, and hustling was appealing because it was lucrative, it was against the law, and it was congruent with what was by then my fairly serious drug habit. I snorted cocaine almost nightly, smoked a lot of pot, and occasionally snorted heroin. I also took lots of pills and got drunk every night. I have always admired stylish outlaws of all sorts, and my drug use together with a good deal of shoplifting already gave me a private status I liked; earning my living by means outside the law seemed at the time like something I wanted to try. It still has a certain appeal, I must admit.\     I called up the number for an escort agency I'd found on a printed ad, and after responding to a couple of simple questions (such as, Have you done this kind of work before? to which I replied, Well, I understand what kind of work it is), I agreed to come in for an interview, where, I was told, I would be expected briefly to remove my clothes.\     I arrived precisely on time since the agent had asked me not to be early. I waited a few minutes on a red upholstered chair, overhearing the owner speaking to a client on the telephone and his colleague interviewing another aspiring escort in the adjacent room. The owner was saying into the phone, Tell me, what kind of men do you like? ... Of course I could send over a black man! James is twenty-four, six-two, principally a top, very nice. He's an athlete.... Would I be sending him to you if he was dangerous? The owner sat before a small, elaborate desk; I could see on the desk only index cards, pens, and fifty- and hundred-dollar bills. He was wearing tight shorts and a tank top, and everything he said was in a surprising tone—it was more aggressive, or more tender, or nostalgic, or surprised than I would have expected, as if things had an eccentric meaning for him.\     The interview in the next room did not seem to be going well. The interviewee was very shy and self-effacing, and the other man sounded frustrated and slightly mocking.\     During my interview with the owner's colleague—a large, rather ugly man in his late forties—we frankly discussed my versatility and experience. I said that I was sexually versatile, but could not agree to do everything with everyone: I'd fuck a man I found attractive, and on a good night I might let such a man fuck me, but I couldn't promise to get a hard-on for a man I didn't like. The man interviewing me said that no one expected me to get an erection at the drop of a hat; but would I let a paying customer suck my dick? Yes, I said, I suppose I would.\     He told me how the business was run and the terms of the arrangement: my fee would be $250 per hour, of which the agency would get $100. I would be expected to bring them their money at the end of each job. Regular customers from years ago, when the rates were lower, were charged the old rate of $200, of which I would make only $100. How many of those are there? I asked. Not many, the man said. They're mostly dead. This was not encouraging, but I let it pass without much thought. Then I was asked to show the agent my body. I removed my shirt and then let down my pants. I was a little cold and more than a little nervous (and not at all aroused), so I was worried that the impression I made was, well, scant. But I was confident, I said, that under different circumstances my true endowment would make itself apparent, and I told the man that I had never had much in the way of complaints from lovers. The agent seemed to believe me and took down a measurement I was happy to accept. He and the owner, who joined us when I was nude, told me I was hired on the spot, and that I should buy a pager with the proceeds from my first call, which would turn out to take place that very night.\     I left the bizarre apartment—lots of chandeliers and mirrors in the two small, brown rooms, and a dog in the kitchen—and went downtown, in the opposite direction from where I live. It was 8:45 P.M., and I didn't feel like going home. The interview had taken forty-five minutes: three times as long as they had said it would take, which I noted with some satisfaction. I felt they had liked me, and I was glad.\     On the subway after the interview, I thought to myself that working for the agency would be very different from my experience at Rounds. The relationship that develops in a bar and subsequently on the taxi ride to the john's home or hotel is often loaded with the suggestion—as with my "uncle"—of a developing friendship and intimacy; thus the ugly feelings, at least on my part, when the little amitié comes to its abrupt, commercial termination. The mediation of an agency gives a more businesslike dynamic to the whole transaction. As in psychotherapy, both parties benefit from the structured time and the payment of a set fee. And the men who can afford the agency's "high-end" rates are generally less troubled by the expense.\     I had something to eat, phoned my answering service (no messages), and went to my favorite EastVillage bar. I had a drink and found, to my surprise, that I had no interest in meeting anyone, or even in sex, if it wasn't going to add something to the nonsexual till. I felt arrogant, as if my services were too valuable to give away, which was a wonderfully empowering state of mind. This feeling would later contribute to my difficulty in sustaining sexual interest in men I was attracted to but not in love with. The arrogance eventually became a psychological burden, an unwanted defense. But at the time it felt pretty good. I was beholden to no one—that's how I felt. I couldn't be rejected because I wasn't available, except for a price too high for the guys in that place to afford. I had no desire. Normally my lust for company makes me vulnerable. But that night I was untouchable, maybe for the first time in my life. Someone casually said to me once that anybody can be a hustler. But any hustler knows that's not true, and that night I knew that I had the looks, the courage, the recklessness, and, now, the agency. I was ready for my new life.\     I phoned my service again and found that the agent had rung. After a brief call to him, I nervously got into a taxi and headed for the Carlyle Hotel. The agent had told me that the client, a businessman from Texas, wanted to take me to the bar downstairs for a drink before going back up to his room, which was fine with me, though the agent didn't like the idea. He said it was a waste of time, and it turned out that he was right.\     I was surprised by the ease with which I was able to walk through the lobby of the Carlyle and into the elevator with no questions asked at 11:00 at night. I suppose if I had been dressed less well, or arrived even later in the night, or was black, I might have been stopped. But I just went on up to a high floor of the hotel and knocked on the door. A red-faced man in his sixties answered and spoke to me in a moderate, soothing Texas accent, and we shook hands. I asked to use the toilet before going down to the bar, and while I was relieving myself, the Texan peeked in and politely asked me if he could watch. I agreed.\     In the bar downstairs we sat at a corner table and John (I believe that was actually his name) put his hand on my knee, which I noticed that several people were able to observe. I thought it was strange that John did not mind being seen with me in this cozy, romantic public situation. He was married, he told me, and the agent had told me that he was very wealthy. He had children and was in New York for business. But I figured that if he wasn't afraid I had no real right to object, and I tried to enjoy the attention. John asked me what I did besides this, though he did not appear to be very interested when I proceeded to tell him about my background as a student of music and philosophy, my interest in writing, and my work in publishing. He told me about his wife and children, who were older than I. John was cheerful and a nice enough guy, though without a great deal of charm. He neither attracted nor frightened me. I felt indifferent about what was to come, and I was bored with chatting.\     John asked me if I had condoms with me—the agent had told him I would. I didn't. I honestly explained that this was my first night working for an agency and I hadn't had time to stock up. I couldn't really imagine we were going to need any condoms, but I said I would go out and find some on my own time and come back as quickly as possible. John said he wanted to come with me, though, so he signed the check and we got into a taxi and found a deli a block away. I got out and paid for the condoms and we took the taxi around the block and went back into the hotel. John seemed almost proud to walk through the lobby with me at a few minutes past midnight.\     That first night, especially after forgetting the condoms, I was very nervous and it showed. We did not have occasion to use the condoms we'd gone out for. I found it impossible to relax. I recall John lying on the hotel bed and me standing to the side trying in vain to bring my dick to life. John, I believe, wanted to give me a blow job, but he was not interested unless I could offer an erection, and I simply could not. He was wonderfully understanding and forgiving, and I did my very best to make the hour erotic somehow. I could sense that John was disappointed, but I believe that in the long run he got some degree of the pleasure he felt himself entitled to.\     The work I did that first night for the agency was the most difficult of its kind that I have ever done. A relaxed atmosphere and a hard-on are certainly preferable to emotional tension and its physical repercussions, both for the client and the escort, but they can't be forced, I was uptight and I punished myself for it, which is not the way to achieve an erection. I was not at all attracted sexually to John, but in the subsequent months I learned how to make almost any situation with a client sexy by focusing on the fact that he is attracted to me. Eventually I would use the client's excitement to trick myself, or my body, into believing that a sexual response was appropriate. This capacity for deliberate self-delusion is at the heart of the whole matter: the way comfortably to take a new role is to make it a habit. But habits are hard to break. I was pleased with myself when I found that l had learned how to perform for my clients; I didn't reflect, at the time, on the consequences of this new facility. What I overlooked was the fact that I could no longer relate to people at all except in this new, assumed mode. Before long I had become a fake. I was good at it, and I liked it, and there are times now when I miss it. I was protected, as a hustler, by my invented self. Unfortunately, the invention was too simple to serve any but the most banal situations, so I began to avoid any but the most banal.\     I spent just over two hours with John, including drinks and the trip to the deli. Before I left, he handed me slightly more than the fee for one hour and asked if that was all right, implying that an hour's fee was all I had really earned. I was too unsure of myself, then, to get the full fee for two hours. I did manage to say that the agency expected him to pay for all the time I had spent with him, and he turned over a little more money. What I had made, then, was not enough, but it was a lot. It was roughly equivalent to what I'd been making (and make now) for working two whole days. And it was tax free.\ (Continues...)

\ Publishers Weekly - Publisher's Weekly\ Now the assistant to the general director of the New York City Opera, Whitaker writes honestly about his experiences as a hustler and drug addict. After moving to New York in the late 1980s with a boyfriend, little cash and no contacts, Whitaker earned a degree in philosophy, wrote a novel and went to work in publishing as an editorial assistant to Gordon Lish. By 1997, he had acquired a serious dependency on cocaine and was having "a great deal of sex with strangers, some of it unsafe." In order to support his drug habit, he began working for two escort agencies and, in the next 20 months, conducted business with more than 100 men before giving up his sex work and going into recovery. Relying on a mix of erudition and titillation, Whitaker quotes Leonard Woolf, Wittgenstein, Thoreau, Andrew Marvell and Pascal as he relates the explicit sexual details of his work life. He's at his most astute when analyzing how his parents' highly unstable, overtly sexual relationship and his own complicated love/hate bond with his father set the stage for his hustling. Overall, despite the literary references, Whitaker's relatively modest psychological insights are overwhelmed by the far more compelling pulp narrative of a young man finding salvation on the brink of ruin in the big city. Agent, Malaga Baldi. (Oct.) Copyright 1999 Cahners Business Information.\ \ \ \ \ Bay Area ReporterIt's a delicate, precious mix, and Whitaker has skillfully mastered it.\ \ \ Chicago Free PassHe is a talented wordsmith and can spin a fairly engaging story.\ \ \ \ \ New York MagazineAssuming the Position: A Memoir of Hustling. . . must be one of the few examples of its genre to splice explicit sex with ruminations on Nietzsche and Wittgenstein.\ \ \ \ \ New York ObserverThe title is titillating, and the rest is clever\ \ \ \ \ Out Magazine. . . An honest portrait of a devastating journey\ \ \ \ \ Paper Magazine. . . a sober...Wittgenstein- and Freud-quoting look into the often juicy (though more often icy) life and times of a gay prostitute in New York City.\ \ \ \ \ Washington Post. . the psychological dynamics of these encounters are what's truly interesting.\ \ \ \ \ Kirkus ReviewsWhitaker's flaccid memoir of life as a gay male prostitute denies the reader even the giddy thrill of voyeurism in service of an existential life lesson which even Sartre would have decried as banal. Whitaker begins with the reason he began hustling: spite toward an ex-boyfriend. After such a startlingly shallow admission, the reader is off on a roller-coaster ride of cheap sex at high prices. Whitaker describes tricks and encounters with men, men, and more men—neurotic psychologists, horny doctors, businessmen from out of town, Broadway composers, even a celebrity whose identity he protects. We travel with him to the penthouses of New York's elite for all-night orgies of sex, drug use, and debauchery. One of Whitaker's chief concerns—will he be able to "perform" with men to whom he isn't attracted?—offers a big clue to the failure of the book: if he wasn't interested in what he was doing, why should the reader be? Interspersed with these recollections of the trials of life as an odalisque are existential ruminations on life, love, sex, and identity. Whitaker trudges out various philosophers and authors—including Wittgenstein, Virginia and Leonard Woolf, and Thoreau—more to prove that he's college educated than to ponder the meaning of life as a hustler. His journal entries, which feature such detours as his maudlin commentary on actress Tallulah Bankhead and a reading list (Sontag and Shakespeare), bog down any narrative thrust he might have developed into a great slurping sound of self-absorption. Whitaker has apparently learned a life lesson through his experiences as a prostitute, and he's obviously writing for some sort of emotional purgation;however, such a catharsis would be better achieved on a psychiatrist's couch rather than boring the reader with sex so dull and journeys of self-discovery so morose.\ \