The Pleasure Boy 15

The very next evening in Lisa's room, when I made good on my promise to report the conversation with Mitch, Lisa asked if I needed her to take things slower with me. "No, Miss," I answered. "The fact is that I love serving you, and being useful and used. It was the label that bothered me - being defined as 'a submissive.' Mitch helped me understand that though life shapes us, it does not define us. People use words to think and speak with, but they do not control us unless we let them. My only problem is to be authentic - and try to do what I am doing well. I know that as your assistant , I will get plenty of training and experience topping your clients. I don't know yet how I will feel about this, but will feel what I feel when the time comes. For now, what you're doing with me is fine. I understand that I'm supposed to communicate my feelings honestly - in my journal entries and on the fly, as we do things. I understand that my safeword 'amber' will get you to ease off if I need that; that 'red' will get you to stop and listen to a problem, if I'm having one. I trust you, and I trust Mitch and Lotte. If I need to discuss what you're doing with me, I'll let you know."

"That's good," Lisa said, "because I was planning to peg you tonight - like I did at your initiation, if you remember. I'm supposed to begin your Submission Training, and pegging is an important marker of your feelings as a submissive. Some men find it humiliating or threatening. Others enjoy it. At your initiation, you didn't seem to mind."

"I didn't."

"We saw. But I was using a very slim dildo, and going easy on you. We wanted to test you, not scare you away."

"The training now will be much tougher, as Mitch and I will be pushing your limits."

"I understand, Miss. I'll use my safeword if I really need it."

"Good."

"All right then. Present your bum in the Worship posture. I'm going to plug you. I'll start with a size that we know you can take comfortably, and work up, week by week, until you're ready for Mitch's cock. In a few weeks, he's going to fuck you. Then we'll get serious about deep-throat training until you're ready to take him that way too. You'll find yourself spit-roasted before you know it, but you'll be ready for it."

"Yes, Miss," I said. "I'm looking forward to that, I think."

"All right, no talking now. Just relax. Here it comes."

With my butt in the air and my face on the floor, I couldn't see what Miss Lisa was doing. But I could feel or imagine every step. She worked very slowly. First, she walked around behind me and knelt. She stroked and patted my bum for awhile to get herself in the mood, and establish the physical contact. Then I heard her pulling on a rubber glove and unscrewing the lid of a jar. A cold, slippery finger circled around my anus and then pushed its way inside. "Squeeze my finger," she said, "as hard as you can.

I clenched my buttocks hard and tried to hold her. "Relax those cheeks," she told me. "Try to grip just with the sphincter. The big ass muscles aren't helping."

I tried to relax my buttocks. "That's much better," Lisa said, "but you're still too tense. Hold my finger, but just with your hole. Relax everything else."

When I could do this to her satisfaction, she said, "Now relax that sphincter"; and when I did so she pulled her finger out and added more of the lubricating jelly. Then again the cold finger circled my hole and thrust in, giving pleasure as it did so. Again she had me grip the finger with my anal sphincter while keeping my butt cheeks loose. Then she had me push back with my whole body, taking that finger deeper inside and squeezing it as I did so. After some practice at this, she got me to fuck her finger as it impaled me, stimulating my prostate as I did so, while she held her hand quite still. Though nothing touched it, my cock stood up of its own accord and I felt the semen rise in my loins.

"May I cum, Miss?" I begged her.

"Not yet," she answered. "Stop moving now."

I stopped and, in a few moments, lost my erection and the feeling that orgasm was near. We remained still like this, with the finger pleasurably inside me but not moving at all.

When I was calm again, Lisa said, "Now you may stimulate yourself and cum, but you're not allowed to touch yourself. You have to bring yourself off on my finger."

"Start slowly. Back and forth. Get yourself aroused again."

"Squeeze that finger."

"Pretend its a cock and try to give it pleasure, as you take pleasure for yourself."

"That's it. Faster now. Fuck my finger with your ass hole. Show me what a slut you are - a needy male slut who needs to get his rocks off. Just tell me when you're about to cum."

As I worked myself on her finger, my erection came back and again I felt the seed rising. "Miss, I'm about to cum," I warned her.

"Fine," Lisa said. "Cum now." She turned alongside me and cupped her other hand under the tip of my penis. When I came, she caught most of my semen in her hand. "Now clean my hand and thank me," she ordered as my breathing steadied.

I bowed over her semen-filled palm, and lapped up my offering. "Thank you, Miss," I said. "Thank you for this lesson."

"You're welcome boy," she answered. "That was the beginning of your training for anal sex. You're going to be doing it a lot."

She took a small butt plug from a box with eight of these in increasing sizes and lubed it up. She had me present my bottom hole again and gently worked it in. "There," she said. "Now we'll start stretching you."

"Go back to your room now, and go to sleep. Leave the plug in. Remember that you're not allowed to wank without permission. You can take the plug out tomorrow morning and return it to me then."

"Good night, my dear." She kissed me.

"Good night, Miss," I answered, returning her kiss. Again I thanked her for the lesson, then waddled stiffly to my room with the butt plug up inside me, imagining how it was going to feel when Mitch fucked my well-prepared ass hole with Lisa watching.

At the start of my geisho apprenticeship, my only thought had been of part-time work to pay for years of university tuition in preparation for an academic career. My plan was to major in history - to understand how and why it had come to pass that our planet, Spaceship Earth as someone called it, was running itself so poorly. My father had wanted me to study something practical and take over his business eventually, but I had no desire to do so. I had the values of my own generation, not of his. I was bright, articulate, and well-read for my age. But in most ways, I was a pretty ordinary 19 year-old kid - of the cohort I belonged to.

In just a few weeks, my life had changed completely. Testing had shown my Mom, herself a retired, senior geisha, that I had inherited the interest of both my parents in BDSM, with a bent for the submissive role; and at her suggestion and with her help, I had been accepted as a pupil by Mistress Charlotte, an old friend and colleague of hers. I had been enrolled in a beginner's class at the Geisha Guild school, and would be a journeyman geisho in a year, if all went well - trained as professional sub, eligible to work, part time or full time, as an assistant to a Dominatrix in a commercial dungeon, or as someone's paid escort or companion. As one part of my training, I had been placed in close submissive relationship with a more senior pupil - a girl from the mid-West, just a year old than me named Lisa Schmidt, just completing her training as a Dominatrix.

Even my family was changing around me. With me in training and out of the house, my mother (known in the Guild and BDSM Scene as Mistress Hannah) began to think about coming out of retirement - against my father's wishes. He would have preferred that she stay home and take up some harmless hobby like painting or pottery; but her plan was to return to geisha work with clients, (instead of the teaching and admin work that she'd been doing). Her plan was to open a mentoring service, specialized in helping kinky couples transform their D/s game into a 24/7 lifestyle. In discussing these plans with her friend Lotte, and at Lotte's suggestion, she had accepted Lotte's pupil Lisa as her intern and assistant. Lisa would complete her apprenticeship working for my Mom and might continue to work for her as a paid employee once she graduated. Doing so, she might continue to practice her skills of lifestyle Dominance with me, under my Mom's and Lotte's supervision.

Please imagine the impact of all these developments on my identity and sense of self. Just weeks ago, I'd been an 18-year-old boy, fresh out of high school with a steady girlfriend We had necked and petted and (just recently) 'gone all the way' a few times, but that was the extent of my sex life. By now, I'd had experience with two men (Mitch and Joe) and with three adult women (Lotte, Gayle and Lisa); I'd learned to lick pussy and suck cock and taken it up the ass once with a strap-on. I'd been spanked for pleasure, caned once as punishment and was already typecast as a sexual submissive and (it was suspected) a pain slut, as I'd been visibly aroused both times.

The obvious, undeniable fact was that I loved all this and wanted more. I was still just an apprentice geisho - not even that, just a probationer - but it was clear to all around me, myself included, that I had a real vocation for D/s and kinky sex, the way that some young men and women are said to have a vocation for the priesthood, or medicine or music or the military, I'd by no means abandoned my plan to study and write history as an academic; but I already knew that whatever I did with my life, submissive sex was going to be a big part of it. I was still getting used to that idea.

Meanwhile, life went on. Under Gayle's direction, Joe had announced over dinner one night that the dynamic of his marriage had altered - that his formerly submissive wife was now his Mistress. When the meal was finished, we witnessed a re-collaring ceremony in which Lotte removed the collars from both Gayle and Joe, as they knelt before her, changed the tags on both collars to reflect this couple's altered relationship, then placed the re-tagged collar round Gayle's neck and had her stand and put the altered collar on Joe. We applauded and wished them well.

Then Lotte took the couple by surprise by requiring from each of them a public explanation. Gayle went first, to describe how learning some skills of Domination in her geisha training had liberated her inner bitch and altered her feelings about her marriage. "I found that though I loved Joe dearly, I resented my subservience to him and wanted to end it." Joe had suggested that they experiment with switching, and when they'd done so, found that they were both happier with her in the Dominant role.

Next, Joe explained that his training had led him in the opposite direction. Partly from meeting and Topping me, he'd come to recognize that his assertion of Dominance had expressed not so much his authentic temperament as the ambient culture of society. There was this expectation that men should be Dominant, not content as I seemed to be in a submissive role. When Gayle had talked about her resentment, he'd readily offered to be her submissive on occasion, when they felt like switching roles. The outcome, as Gayle had described, was that when they did this, they both felt happier.

Talking it over with Lotte, their Mistress had recognized a teaching moment and required that they publicly announce and explain their altered relationship. Joe would now use the rest of his apprenticeship to learn not just the skills, but the feelings and rewards of the submissive stance, while his wife did the same as his Domme. Lotte concluded, "Now, whatever turn their relationship takes, however they decide to run their marriage, as professional geishi they both will have had vivid experience of both the Dominant and submissive roles. It's a real gain for both of them."

The evening after my conversation with Mitch, Mistress Lotte called me to her room. "Last night with Lisa, you began Submission Training," she stated: "the standardized program for all professional submissives. Mitch and Lisa will put you through it; they will report your progress to me; and I will intervene as I see fit. To complete it, which you must do before your internship begins, you will have to satisfy us that you have learned the skills and acquired the attitudes and values that the Guild expects of its qualified professional subs. I'll warn you now that the training is difficult, and will require your maximum concentration, endurance and effort. It demands your explicit consent - up front, before you know in detail what is involved. Tonight I will give you just a taste, so that you know what you are consenting to. It will be difficult and painful. You may use the 'amber' safe word at any point to slow it down and talk it over, but if you use 'red' to stop this training, you will be transferred out of here to a less demanding type of geisha work - a less demanding pleasure-specialty - than ours."

"Any questions before we begin?"

"None, Mistress. I'll do my best," I answered.

"Very well," Mistress Lotte started in. "As you know by now, professional submissives are required to control their orgasms. They're not allowed to masturbate or cum without permission. Tonight, the name of the game is 'tease-and-denial.' You must think only of my pleasure and suppress your own. I'm going to play with you, and you must try not to cum. I guarantee that you will fail, after which you will be punished. Over the next weeks and months, you will be tested this way, again and again, until your concentration and self-control are strong enough to save you."

She had me lie on her rug with my head in a U-shaped pillow which supported it comfortably but prevented it from turning. Then she knelt beside me and stroked my cock with a feathery touch until my erection was painful. Next she bent over it, kissed its tip lovingly, and grabbed it with lips. Taking it in her mouth, she licked and sucked, bringing me closer and closer to climax while I reviewed the digits of pi to keep from cumming - '3.14159265' - again and again, to as many digits as I'd once memorized. It didn't work. In eight minutes, 23 seconds (as her stopwatch showed us), I exploded.

As she felt the climax building, she held my cock completely in her mouth and held still so that she caught all of my semen and ruined my orgasm. Then she kissed my mouth, feeding some of it back to me and licking the rest of it over my face. "You lose," she said.

"Also," she went on, "I could tell you weren't thinking of me or focusing on what was happening. You used a trick - counting sheep or whatever - and tried to go somewhere else. That's disrepectful."

"So you have offended in three different ways, and must be punished for each of them. For going elsewhere, not thinking of my pleasure, I have already punished you by ruining your orgasm. For using some trick to do it, I think nine cane strokes will be appropriate. And for cumming without permission . . . , have you ever experienced punishment bondage?"

"No, Mistress. I don't even know what that is."

"It's a combination of prolonged sensory deprivation with bondage in a safe, but uncomfortable position. You're going to spend three hours that way. You won't enjoy it."

Calling Lisa to come and help her, she took me down to the basement dungeon where she saw paying clients, and also punished deserving apprentices. First, after explaining what I was being punished for, she had Lisa deliver the caning I was due. I had to bend over a bar while Lotte clamped my head between her thighs and held my crossed wrists high up behind back. "Nine strokes, Lisa," she said. "It's important that you make him feel them. You're teaching him a lesson that he has to learn."

Then she sat me in a special frame - the 'stocks,' she called it - which held my feet widely apart and roughly a foot above the floor while my wealed bum was placed on a roughened plank that would chafe the cane stripes when I squirmed around. Next, she fitted me with a bondage hood that encased my whole head in leather, covered my eyes and ears with thick pads, so that I could not see or hear, and put a ball gag in my mouth so that I could not speak but left my nose free so I could breathe. She pushed a wide leather strap under my knees, doubled me over, then passed its ends up through my armpits and fastened it over my back with a buckle which held me in that position and dug into my shoulders without cutting off my circulation. Last, she gave me a short bar to hold with both hands, telling me that dropping this would be my safe word. It was wired in such a way that a bell would ring if I let it fall, ending my punishment but dropping me from the whole program unless I'd been in real trouble.

There was a cot in the room, where Lisa could sleep near me for safety's sake. If the bell rang, she could wake up and release me. There was also an alarm clock that would wake her at two in the morning to put an end to the punishment (except that on less than four hours of sleep, I'd be a wreck the next day). Then Lotte kissed me, and bade me think about orgasm control and the educational value of pain. She bade us good night and left us. Lisa amused herself by stroking my shaft for a few minutes, then left off when she'd given me another uncomfortable erection, and went to sleep - leaving me to the predicament I was in. As Lotte had warned me, I did not enjoy the experience. It was a miserable night.

I wish I could say that this one lesson was enough to teach me, but this was not the case. It had to be repeated many times before my trainers were satisfied - that I could perform or be stimulated indefinitely, stay focused on my partner's pleasure and only cum when allowed.

Apart from hands-on training of this kind at Lotte's house, you may be interested to know more about the curriculum at Guild school.

The Hedonics class - a survey of the Pleasure industry remember - was mostly reading, lectures and class discussion. There little to do, but quite a lot to remember, much of it pretty dry.

The Escort class, by contrast, cut into our evenings and weekends. As a group, we were assigned to a more senior class (in its last few months before internship) and rotated around, to work with its individual members, and sometimes with our instructors, who pretended to be our clients. By turns, we had to be either amusing or blandly inobtrusive, responsive to our client's mood and to the current situation.

The Groups class gave us a lot of theory from social psychology and small-group sociology. We gained some practical experience as well, by describing and critiquing the processes of various groups that we were sent to watch. We also got practice in leading several types of group, depending on our areas of specialization. For example, I was sent to give a talk on Guild training to a group of curious submissives.

The Sex class was a scaled down version of our activities at Lotte's, supplemented with films, readings and discussions of specific practices. It was intended to do for their minds what a regime of butt plugs would do for their sphincters.

The Phys Ed classes at mid-day taught us to take pride in our bodies, and to keep them functional and good-looking. It dove-tailed closely with the 'ballet' training in posture and movement that I received in Submission Training at Lotte's.

In sum, the Guild School's role was to make me a passable geisho. At Lotte's I became professional submissive, with some basic skills of Dominance as well. With three months of this training, I did well in the evaluations that followed and passed out of probation. Mistress replaced my white probationer's collar with a tan one. I was now an accepted apprentice, now entitled by Guild regulation to a fair shot at qualifying as a journeyman, whether in BDSM with Lotte or in some other specialty.