The Pleasure Boy

Note: This is the first of what I plan will be a long series of short episodes in the training and career of one Jim Woodruff, a modern American geisho or pleasure-boy.

Clients often ask me how I became a geisho. Some are just curious. Others think that I will feel humiliated when I answer them, and seek to enjoy my shame as I do so. Rather than disappoint them, I pretend to be embarrassed when I tell my story; but actually, I feel nothing of the sort. I’m rather proud of my profession. There’s still too much puritanism in North America to give simple pleasure — pleasure without enhancing drugs, and for its own sake — the respect that it deserves.

The modern, Westernized geisho or geisha may or may not have actual Sex with clients. As in old Japan, that is a personal choice. Like our Japanese forebears, we may sing or dance or just facilitate conversation. But the essence of what we do these days is more physical and sexual than it used to be. Today, among much else, we teach the arts of pleasuring a partner, and of pleasuring oneself. We teach the uses of mouth and anus, as well as penis and Vagina as Sex organs and, above all, we teach our clients to play with their imaginations. We help them to understand that Sex is more than mutual fun, but basically a power game about taking and being taken — about the weakness of desire and conquest, about the power of submission and surrender.

In this way, we regard BDSM not as a kink or perversion, but as a prime dimension of authentic sexuality. Then we go on to explore its paradoxes: the dialectic of pain and pleasure, of shame and pride, of bondage and freedom. We use punishment, restraint, exposure and sensory deprivation for their erotic, psychosexual qualities. We work with clients one-on-one, and also teach the rudiments of our skills in ‘workshops,’ to couples and small groups.

Some of us work in luxury hotels. Others at spas, saunas, or public baths, at beauty salons or at their masculine equivalent. Others again just provide escort services — exclusively at public events, restaurants and other spaces. Some of us — taking security precautions — visit our clients homes. Some of us function as facilitators at business conventions and special group events. Some, like the courtesans of France or Venice, attach themselves to a single wealthy patron. Some, like my mother, eventually retire, settle down and raise a family. In fact, there is no one way to be a modern geisho or geisha. We have our talents, specialties and reputations.

My own career as a pleasure-boy originated with a sarcastic remark from my father — at the dinner table one November evening, when he asked me what I planned to study (at the prestigious university in New York City to which I’d just been admitted. I had just turned 18, and was in my senior year of high school. When I told him that I wished to major in history, hoping to go on to grad school and an academic career, he asked angrily if I expected him to pay my tuition and living expenses while I did so. If that’s your plan he said, you’d better become a geisho like your mother and work your way through college. “I intend for you to inherit my business, and to run it on your own some day. I will pay your way to study something prac­tical,” he said, “like business or medicine or law. But if your ambition is just to rummage in the past, you’re on your own.”

I knew better than to argue with him when he was in that hard-assed mood; so I said nothing. But, catching my mother’s expression as she heard this, I knew I had to speak with her in private. She had been a successful geisha herself. My dad had been her client, and in a sense, I felt, he still was. He had married her, giving her status and a family, but it was her professional skill at pleasing him always, and guiding him on occasion, that made their marriage work.

I thought about his comment, and my own situation. I knew I had no interest at all in what he called practical affairs.’ Nor did I have the patience or calling to study medicine. I was interested in how people made their choices — not from the perspective of a psychologist who wanted to know how our brains work, but from that of a historian who looked at the crazy things they did, and at the contexts behind their choices. It seemed to me that things turn out as they do only partly as an outcome of human nature, but largely by accident and as the unintended result of what looked rational (or sensible, or just attractive) at the time. Despite Isaac Asimov and his ‘Foundation’ series, I knew we’d never be able to predict future history any more than we can predict the weather more than a few days in advance. My interest was just to know about the people who made history, and about the events that actually went down. I wanted to think and write about what had happened, and teach it to others if they were interested. I was not going to let my father determine my choice of careers.

I also thought about my mother’s profession, and was curious about it. I knew that she was a geisha, and that people snickered when that career was mentioned. She never talked about her work, but made no secret of what she did and was clearly not embarrassed by it. I knew she no longer saw clients, but did admin work and taught to younger women.

I admired my mother but had never thought of following in her footsteps. She had never suggested I do so. In those days, as a teen-age boy, I was thinking about Sex a lot, but in connection with girls my own age, not my mother’s career! I had no idea what was behind my dad’s remark — where he was coming from when he made it. When dad threw her profession in my face like that, it showed a certain contempt for both of us. I was hurt, and I worried that mom might feel hurt also.

Next morning, after he had left for work — in a corner office at his electronics firm — I asked Mom what she thought, and whether she could get my father to change his mind. “No,” she told me, “and I wouldn’t try. I don’t think I could get him to support you on a course he feels contempt for, and it would be bad for all three of us if I succeeded. But, if you have the temperament for it, I think you could do a lot worse than train as a pleasure-boy, pay your own way, and show your dad that you don’t need his help.”

“You’re good-looking enough to make it as a geisho,” she went on, and having been a geisha myself, I will say that it can be a fine and honourable career for anyone who respects pleasure and enjoys giving and receiving it. Also, I still have good contacts in the profession and could help you. If you choose to take that path, your own feelings will be your only limitation.”

“What do you mean?” I asked her.

She answered, “Many people associate pleasure-work with prostitution, and you may do so yourself to some extent. You may feel that it is shameful to give sexual pleasure to strangers for money, or to lend them your body for their use. Though you will always have safe-words and can set your own limits in advance, you will sometimes be renting both body and soul for your client’s pleasure. Everyone who works for a living does this to some extent, but in the water trade (as the Japanese called my profession) we do this in a most direct and obvious way.”

“You can set limits to protect yourself. We all do that. But in doing so you will eliminate potential clients. To the extent you feel reluctance or shame at what you’re doing, this will put off some clients, although some others will enjoy it. As a geisho, you would be selling services and pleasure. It would be your profession to make your offerings as valuable and remunerative as you can without violating your own sense of decency and honour. Others will train and pay you; I will help and advise you if you take this path; but ultimately, in this or anything else, it is yourself that you must please.”

“How will Dad take it?” I asked her. “Will you keep it secret that you are helping me? If he knows, won’t he be angry?”

“I will not keep it secret that I am helping you. And he will be angry with both of us, at first. But he will also respect you for standing up to him and for paying your own way through school. Though he will be annoyed with me at first, and may even try to forbid me to help you, he will not seriously expect me, as your mother, to withhold my Love and support. He knows full well what it will cost him — in our marriage bed and elsewhere — to make me resent him. Also he loves us; and though he has his limitations (like all of us) he is a good man.”

“In the long run, however he rationalizes it, he will forgive us both. In the short term, handling him will be my problem. You don’t need to worry about it. Be assured that I can do what is needed.”

“But I have questions for you my dear, and I must have the truth: How much sexual experience have you had? How would you describe your sexual orientation, and how do you feel about Sex in general? How do you feel about yourself as a sexual creature? I know you’ve been masturbating regularly for several years now. I see the semen stains on your underwear and sheets.”

I blushed and started to stammer something. She made a gesture and stopped me short. “No need to be embarrassed,” she said. Remember that I am a very experienced woman who knows all about men, and knows very well that she has teen-aged son. At your age, if you weren’t wanking two or three times a day I would be worried about you.”

“Now, you’re entitled to your privacy, but if I’m going to help you, there are things I need to know. How far have you gone with your girlfriends? Have you had any homosexual experience? How would you feel about wanking with another boy? About giving or receiving a blow job to a man, or a Pussy-licking to a woman? About fucking another boy, or being fucked? About getting pegged or face-fucked? Are you a dominant or a submissive or a switch?”

“In short, what turns you on, and what would really gross you out? If you don’t know, if you haven’t thought much about these things, I’m giving you a homework assignment. With your own lap top, in your own room, I want you to watch a Porn tape that I’ll give you (a DVD actually), as many times as you like until you’re ready to answer my questions.

She went on, “You will wear a tracking collar as you do so. It will record your pulse rate, blood pressure and skin conductivity, and give us both an objective measure of what floats your boat. It will time itself to the DVD and keep track of the pauses, so you can do this exercise for days — and interrupt to masturbate, as much as you like.” It may tell you more about yourself than you want to know. It will certainly tell me more about you than you are comfortable with your mother knowing.”

“But that is the second point of your assignment. If you are going to be a geisho, you must get used to seeing yourself — and letting some other people see you — from the perspective of that profession. If I am going to help you, you must let me be a geisha to you, as well as your mother!”

“Now, not another word. We’ll talk again in a few days. Meanwhile, think it over, watch the film and let yourself enjoy it. I’ll leave the DVD and collar in your room. Just let me know when your finished with them.”

“Then we’ll discuss the results, and I’ll tell you what assistance I can give you.”

She got up, hugged me and walked away; and for the moment, that was the end of it. But she had given me a lot to think about, and made me see her in a new light.