The Pleasure Boy 02

The Pleasure Boy 02

The 'tape' I was to watch was actually a DVD disc with about four hours worth of miscellaneous porn. It was professionally made, with a variety of body types and costumes, doing many activities that I knew about, and others that I didn't. The collar that mom had me wear was a plain leather band with a battery, some electronics and a data chip to record my body's response to what I was seeing. It made me self-conscious on one level; on another the collar itself was sexy, making me feel enslaved while I was wearing it. Mom later told me that the interpreting software would measure that response when I started wearing the collar and then got used to it, and would allow for this effect in all my other responses.

As I soon learned, however, the collar's only real purpose was to keep me honest when I sat with my mother a whole week later, answering her questions. I did not need it to learn what turned me on. I watched that DVD over and over again, discovering a lot about myself in the process.

First, I discovered my interest in sexual submission. I had known about BDSM in general terms -- known that some people in the scene were 'tops' and some were 'bottoms' -- but I had never thought much about that whole game, let alone seen myself as submissive. Now, watching scenes of men spanking, caning or strapping young attractive women, or of older, voluptuous women punishing men, I invariably found myself more attracted to the submissive, recipient's role.

But the second thing I learned was that I could readily imagine myself responding sexually to men, either as 'top' or 'bottom' or on equal terms. While I had certainly been aware of homosexual relationships, I had never thought of myself as gay. Now, watching nude males fondling and kissing one another, masturbating together, giving blow-jobs, doing '69' or actually fucking in one of several ways that males can be fucked, I learned that the male body could be as visually erotic for me as the female -- and in an interestingly different way. Of course, Greek and Renaissance sculptors had shown this long ago -- to anyone, straight or gay, who's willing to be shown. But it is one thing to see the Michelangelo or Donatello 'David' in a museum and something quite different to watch the clip of a handsome middle-aged man caressing and plowing a twinky youth.

Though I've had plenty of experience with other men since that time, I'm no more 'gay' now than I was then. For sexual purposes, I still like the female of our species a bit more than the male. But that one scene on my mother's film was an eyeopener. For the first time, I learned just how sexy other males could be; and I still enjoy sex with men as a regular part of my work, and sometimes for my own pleasure.

I took a full week, going through that tape at least three times with accompanying manipulations of my 'little man' before I told mom I was ready to talk. Then I returned the DVD and collar to her, but had to wait a few days before she had time to review its data on my responses. Finally, on another morning after Dad had left for work, we had our second conversation about my prospective geisho training.

"So, what did you learn from that exercise?" my mother asked me.

"That I'm a whole lot kinkier and more homosexual than I thought I was," I answered her. There was no point in being embarrassed or evasive. She'd seen the data record of my woodies and wank-offs while I was watching that material. And it was she who given it me to study.

"What does that suggest for my career as a geisho?"

"What do you think it suggests?"

"I don't know," I answered her. What I like to watch, or what turns me on by myself or with a willing lover or playmate, might gross me out completely if I had to do it with paying customers."

"Good answer," she replied. "As I told you, we're not prostitutes selling sex, but facilitators teaching human growth and pleasure. There are just two rules: The first is a rule from the BDSM community that whatever we do must be safe, sane and authentically consensual. What exactly that means, you will have to learn. The second is a rule from psychotherapy about 'unconditional, positive regard.' Like the therapist, in other words, we must pay close attention to our clients; we must genuinely care about them; and we must refrain from judging or criticizing them. Our job is to help them to be what they are, and to find joy in that."

"But Mom, I asked her, "how do those rules help you decide when and with whom to give blow jobs? Why did you have me watching all that porn?"

"Because sex is much bigger than people think it is, and people's sexuality is a big part of what they are. A big part of your role as a geisho will be to help them discover that. Not to pleasure them necessarily, but to help them find pleasure somewhere, or to pleasure themselves. You can give the blow job if you want to, and if you think it will help. Play with your client is sometimes good technique, sometimes not. Nothing compels you one way or the other. It's a matter of taste and judgment. Yours."

"As a geisho you will be free to set your own specialties and limits, and to run your private sex life on your own terms. When your father first tried to get it on with me, I told him that if he had me, I would cut him off as a client. From then on, our relationship was our private affair."

"All we've learned so far is that your specialty might include a fairly broad range of sexual interests. What that tells me is that you need a teacher who will give you actual experience and skills to match your interests; and I think I know one who might be good with you."

She paused and stayed silent for a bit, giving me a chance to respond. "You know," I said, finally, "I think this is a weird conversation to be having with my mother."

She laughed. "I'm doing a geisha number for you now, not the mother number. And that's the exact reason why, if you want to go ahead with this, I will find another teacher for you, and not try to teach you myself."

"What do you say? Should I find you a teacher or not? Can you see yourself as a geisho?"

"I think so," I told her. "If you see nothing wrong with it and are willing to help me, I'm ready to try this. Right now, I'm mostly delighted at the idea of putting myself through school without Dad's money.

"All right," Mom answered. "You'll either find that you have a calling for this work, or you won't. I'll help you all I can, but there is one condition. I want your promise that you will be honest with yourself to the best of your ability, and completely truthful when your teachers and I ask you questions. I will try to respect your privacy, but there are things I will have to know."

"In return, I promise you that there are no wrong answers. I'm only asking these things in order to help you correctly. If you're too embarrassed to answer something, that only limits what I can do to assist you, and puts you at the mercy of my guesswork. Now, do I have your promise?"

I nodded.

"Not good enough," she said. "Say it out loud."

Yes, Mom, I told her. I promise to answer your questions fully and truthfully to the best of my ability.

"Good," she went on. "Now, tell me what you want to do."

"I want to enroll at Columbia, major in history, and then go on to grad school and an academic career, or study political science or law if I change my mind. I want to pay for my schooling and support myself by doing part- time geisho work. I don't want to rely on, or be influenced by dad's control of the money."

"OK," she said. "With those plans, even after you finish your studies it will be good to have a ready way of making a living, regardless of the field you finally choose. For the freedom this will give you, if nothing else."

"What I suggest is that you ask for a deferred admission to the university -- a year off before continuing your studies -- and use that time to qualify for geisho work."

"I know a woman, an old friend and colleague in the business who is now a free lance trainer -- along with her husband who submits to her. I can ask her to take you on for testing, training and some experience with actual clients, under her supervision. If she accept you, you can expect to be trained in the basics of geisho service both to her and to her husband. Then, depending on what she learns about you, and with your consent, she'll lend or rent you out to friends or clients of hers who will use you and give her feedback on your performance. At the end of the process, she'll prepare a report card that she'll discuss with you, and with me also, if you give that permission. You won't make any money yet. Any money she can make from you she'll keep as her fee for teaching you. You'll be indentured as her apprentice. In effect, as her temporary slave."

At that point, I was squirming in my seat, trying to hide my erection. Of course, my mother noticed. "I can see you're aroused," she said. "For what we're planning, that's a good sign. But your choice must be explicit. What do you say? Should I call her and set up an interview, or think of something else?"

"Please call her," I answered. "I know I'll learn lot."

"You will," my mother said. "Just trust her, obey her, and be respectful, as I know you can be." She beckoned me to her and kissed my forehead, giving a mother's blessing. "You'll do fine."

She picked up the phone and dialed. In a few moments her call was answered -- by a voicemail system, obviously; and I heard her leave a message. "Hi Lotte, this is Hannah Woodruff. When you have a chance, could you call me back please? It's about my son James -- 18 years old, good-looking and juicy. He's expressed interest in working his way through university and grad school as a geisho. He needs testing and training and I'm hoping you'd be willing to take him on. Thanks. Bye for now."

She hung up. "There," she said. I've left a message with an old friend and colleague named Charlotte Steiner. She's a trainer now, and one of the best I know. She'll call back, and we'll take it from there."

That was the end of our conversation. A few days went by before there was any news.