The Pleasure Boy 20

The Pleasure Boy 20 (Jim's Internship)

The next two months, as the saying goes, were the beginning of the rest of my life. Not only were they my first introduction to real geisha work; they were also the start of what I was to have of an academic career. For it was just two weeks after my first escort gig from Monique Allard that the fall term started at McGill. Instead of taking a student loan, I'd paid tuition for the fall term with money borrowed from my father - enough for two months living expenses as well, since I would not be getting paid until I passed internship and became a journeyman. Dad was delighted that I was now comfortable asking for his help. Nonetheless, once I graduated, I worked hard to pay him back as quickly as I could. I still wanted him to know that I was serious about my new career and my independence.

My training relationship with Lisa continued, but with much less significance for both of us. She used me as an escort from time to time, and required my sexual service when she felt like it. She was strict in awarding demerit points when I displeased her in any way, and saw to it that these were faithfully recorded in the performance book I kept on myself, as Mitch had taught me early on. We arranged to meet every two weeks for 'maintenance sessions,' in which demerits for that period - those that she awarded, plus those I gave myself - were reviewed and punished.

As she'd been taught, she made a ritual of it: requiring me to strip naked, kneel before her and read each demerit aloud, wording each one as a confession of negligence or failure. Then I had to ask for appropriate correction in a formal way, suggesting a certain number of strokes with the implement she used, but leaving the actual sentence up to her. Next, when we'd arrived at a total, I had to ask for them properly - on my bare bottom, laid on to help me regret my failures and resolve not to repeat them. And finally, I had to lie across her lap, receive the strokes, thanking for each one, and truly feel that each was to be valued - something I needed, to make all well again, and help make me a better person.

If this ritual of corporal discipline seems juvenile to you, as it did to me at first, it was deliberately so. The idea was to make the penitent feel childish and ashamed for having erred as he did. The tawse she used had a painful sting, but well within the range that I could tolerate. Humiliation, more than pain, was the effective ingredient of these punishments.

To this extent, Lisa remained a Mistress to me, now at arms-length unfortunately, while I remained a lifestyle submissive in her charge. I missed the intimacy I had felt with her when she was training me daily, but it was better than nothing.

McGill University had accepted me a year ago, and given me the one year deferment that I'd requested. Now, when I registered and paid the first term's tuition fee, they welcomed me as an undergraduate in their Honours History Program. To have time for geisha work and further geisha training, I gave myself a light schedule at McGill, deciding that if it took me five or six years to get my Bachelor's degree, it would be time well spent because I had been learning a good profession at the same time. My first choice would have been three courses per semester, but I was told that so light a course load would turn me into a part time student, subject to various restrictions. So I ended up taking four 3-credit classes, which would earn me a degree in 10 semesters: 5 years if I took summers off to work full time, as I intended. This gave me more stress than I wanted, but seemed manageable if I used my time well and borrowed from my Dad when I needed money, paying him back by taking escort gigs from Monique over the summers and at other times when I had leisure to perform them. In the event, four introductory courses took up my freshman year:

• research and writing;

• the Russian language;

• a survey of world history and an

• introduction to social science.

Research and writing was a compulsory course which taught us how to use the library and had us turning out a constant stream of papers - mostly on topics that were assigned to us, but also on a few that we chose ourselves. Except for the volume of work involved, this was an easy course for me as I enjoy writing and am good at it.

Russian was a language that I would need to pursue my interest in the history and geopolitics of central Asia. I already had this in mind as my intended area of specialization, partly for its current marketability in the academic world, but partly for its relevance in the history of the Eurasian landmass, and in world history to-date.

The survey of world history, intended as a prerequisite introduction for all future work in McGill's history department, was a broad survey of human history from the emergence of 'anatomically modern humans' about 200 thousand years ago, through the old stone age (the 'paleolithic'), to the advent of sedentism and agriculture some 10-15 thousand years ago, to the emergence of city-states and empires in the ancient world. The course ended on the eve of modernity with the Seven Years War (known to Quebecois as 'La guerre de la Conquête' and in the US as 'the French and Indian War) which is really best thought of as 'World War Zero' because it was a global conflict in which the four great powers of Europe at that time, (Britain, France, Prussia and the Habsburg dynasty in Austria, Spain and the Spanish Netherlands), fought each other for global supremacy, with Britain emerging as victor.

'Introduction to Social Science' was an experimental course given jointly by profs of Social Psychology, Anthropology, Sociology, Economics and Engineering, which sought to provide undergraduates with an overview of current issues and knowledge in the science of human societies as self-organizing systems. More on this later.

Between geisho work, university, and aikido twice a week, the program I'd strapped myself into was just barely do-able. What with the time spent with Lisa and a visit to my parents every other week, I scarcely had room for any other activities or social life. Fortunately, my life with that load was full and well balanced, and would be easier when the writing class and first-year Russian were out of the way. In the introduction to social science and the survey of world history, I was at last at grips with the field I hoped to study. As a geisho I often met interesting people, and had a varied sex life that was sometimes fulfilling when I really 'clicked' with a client. I found both spiritual depth and great physical exercise in practising aikido. All-in-all, my life as a new journeyman and student was much more stressful than I liked, but it was very good.

Mistress Monique, of Service d'escorte Allard, helped me greatly at this time by recognizing, without protest or penalty, that I would have to turn down a large fraction of the gigs she offered me because my school commitments interfered. Each semester I gave her my class schedule and tried to work out times during the week when I'd reliably be free. But this wasn't easy, and there were always exceptions. From Monique's perspective, my academic ambitions were a major inconvenience, and I knew I had to make it worth her while to put up with them by being extra good with her clients.

Some juggling was involved, because unexpected (or unexpectedly difficult) assignments were given, or because a topic required extra reading time or study. When this happened, I sometimes had to skimp on the schoolwork because once I'd accepted an escort gig, I had to give it priority. On these occasions, most (but not all) of my teachers were helpful too.I made sure they knew that I was working my way through school. When my assignments were finished late, or not polished as well as they might have been -as they knew I could and would do, when I had the time - most of them would make allowances.

Escort gigs had to be booked at least a day in advance, and often took extra time because I would need to be dressed and prepped for the occasion. Usually this was done at Monique's place, rather than at home, because she had special facilities for costuming and grooming, and because I had to be turned out to her specs and satisfaction. She had full time employees to help her escorts do this, but she herself was often on hand to give a final approval.

At these inspections, she would also brief us on the clients we would be serving - especially on repeat clients well-known to her from previous rentals. After each engagement, her escorts were required to file a brief report on their client, and perhaps submit to a debriefing from Mistress Monique if the engagement had been in any way unusual or interesting. In the two months of my internship, mostly in the few weeks before school started, I had had nine engagements with Allard clients, and been called in for debriefing on two occasions.

The first time was just a routine interview after my first gig for the firm. Mistress Monique just quizzed me on my choices and feelings and showed me the feedback she had received about me from the client - a wealthy widow who had had me attend her at a business conference, then take her home and service her sexually. She had been pleased with my performance and marked me satisfactory on all counts.

The second debriefing had not been about her new employee, but about a new client - the Domme half of an FLR couple, who had engaged me (at the discounted daily rate) for a whole weekend to play slave to her submissive husband who could not accept to be straight and submissive all the time, but liked to have a male pleasure slave whom he could use and order around - often in ways that would please his wife. Not having found a gay sub to complete their couple and be under both of them, the Dominant wife would hire a suitable escort for a whole weekend from time to time to keep her husband happy and amuse herself. It being the end of summer, with school not started yet, I was still relatively free. When Monique offered that gig to me, I accepted - and then informed Master Tom that I would have to start my weekend hours with him a week later.

In her briefing, Monique had informed me that Mistress Linda and bill intended to keep me naked at home and would supply any humiliating costume that was wanted for me. As I would need no extra clothing and no equipment, I took a cab to their home that Friday evening with only my kit bag for personal toilet articles, like a toothbrush, deodorant and razor. When I rang their doorbell, bill opened to me, had me strip in their front hall and pose while he looked me over. Then with my street clothes and toilet bag stashed in their front closet, he led me (stark naked and barefoot) down a long corridor to meet his wife.

She was seated at a desk in a room that was obviously her study. "Kneel and bow," bill said to me. "This is our Mistress. I serve her, and you will serve both of us."

I did as he'd commanded and kissed her foot. "Pleasure boy jim, at your service Ma'am," I told her. She was a handsome middle-aged woman, casually dressed for leisure at home, who seemed used to having her way.

"I assume Monique told you what we'll expect of you?" she asked.

"Yes Ma'am. Essentially, that I'm to be a fuck toy for your husband, and an obedient slave to you."

"That's right," she answered. "Give him a BJ now while I watch you. He's been waiting impatiently for your arrival, and I want to see how good you are."

"Start off as my valet," bill commanded. "Help me undress and fold my clothes neatly. Then get me started and do me as you've been trained."

"It will be my honour and privilege, sir," I replied formally, and began to do as I'd been ordered.

I can spare you the details. In a few minutes he was as nude as I was, and already sporting an erection. His circumcised cock was ordinary, but nothing to be ashamed of. His forty-ish body had once been impressive, but was out of shape. I guessed that he'd played football twenty years ago.

I turned to kneel before him, squeezed his bum lovingly with my left hand and stroked his cock with my right. In a moment, he put a hand behind my head and pulled me down on him. Only a fast swallow kept me from gagging. Urgently, he started fucking my face while I kept up, but tried to slow him down. "Take it easy, bill," I heard Linda say. "I want a performance from both of you, not just from him. Go slow, and show me how much you're enjoying this. And you can start by thanking me for hiring him for you."

"Thank you, Mistress," Bill answered hoarsely. "I truly appreciate your kindness." He stopped driving me, and I slowed down. Out of the corner of my eye, I saw his wife slip a hand down the front of her slacks and begin to finger herself slowly. She worked to arouse herself, but not to cum. I could guess what my next job would be.

So it turned out, and thus the whole weekend went. I alternated between doing bill - or letting him do me - for his wife's viewing pleasure, and doing her while she tied his wrists to rings set in the wall and 'forced' him to watch her give herself to another man. Sometimes, bill and I had to follow her instructions; sometimes she left him free to command me. Just once, she had the two of us kneel side by side to masturbate for her so she compare his style with mine. I was forbidden to cum till bill had finished; he was just told to drag it out and make it a good show. On Saturday evening, after dinner,, she had me take bill up on my back and 'horse' him for a flogging. She used a nasty six-tailed martinet which stung painfully and striped him nicely both on his shoulders and on his bum and thighs while doing almost no damage. Through his nude body, I could feel each stroke as he jerked and writhed with every impact.

Sunday evening, just before I left, she had him use that same instrument on me. For my ordeal, they stretched me on a kind of ladder which held my ankles close together just off the floor, and spread my arms above my head so that my sides as well as my shoulders were exposed. The ladder was constructed so as to bend me at the waist, presenting my bum and thighs almost vertically, but my back at a steep angle so that an executioner could flog slightly downward, more conveniently for him than a horizontal stroke would be, and thus more painfully for his victim. Linda counted each stroke before bill gave it, and she directed his target also. "Give number eight on his right shoulder," she would say, "so that it wraps around under his armpit. Give number nine backhand, to mark his left side in the same way. Give number ten in the sulcus, where his ass hangs over his thighs. Repeat the next five in the same place. He really feels it there."

"Eleven,"

"Twelve,"

"Thirteen,"

"Fourteen,"

"Fifteen."

And so it went, on and on, until they'd had their fill of making me suffer. When Monique interviewed me on the phone next day, I told her that the weekend went well. "They gave me a real workout, but they knew what they were doing. I was always safe and the pain felt good. I think they liked working me, and I never had to use a safe word. They said they'd ask for me again."

"Yes," Monique answered, "That's what they told me. I'm pleased. They are good customers and I like to keep them happy. We made good money from that weekend."

"Indeed we did," I said, thinking of the fee that had appeared in my bank account. "I won't be able to give them many full weekends once school starts, but I'd give them a day or an evening whenever I can."

"That's great," the Mistress said. "But it's good to know you can take a hard weekend in your stride."

My work for Master Thomas, at regular hours each week, was simpler to arrange than the escort gigs for Mistress Monique. Its main challenge for me was to play acceptably and adequately with new clients to whom I felt no attraction, when there was no time at all to get to know them. I'd learned months ago - with Mitch and Mika, for example - that I could be aroused and sexually stimulated by attractive people of my own sex. Master Tom had confirmed this at our interview. But I found it difficult to handle male clients when there was no personal relationship or attraction. Oddly, this was not a problem with my female clients. Monique had hired me as a professional submissive, who could give her clients sexual release when they demanded it, and take from them a certain amount of abuse. I found that I could serve even the most difficult and unattractive female client - cheerfully, and with 'unconditional, positive regard,' as the shrinks call it. With her occasional male clients for a guy like me, and with the men at Master Tom's Dungeon, this was much more difficult. I managed it, but only by drawing on a new-found sense of professionalism which I needed now to save my self-respect. Somehow, it made the difference I needed between a highly trained geisho and a rent-boy. I am still amazed that mere labels make such a difference.

As already mentioned, Master Tom and I had agreed on my working hours, and he'd explain my availability to his clients when they asked for me. They liked to play rough, as Mistress Lotte had warned me but, thanks to Tom's good management, this was less of an issue than I had feared. One reason was that for many of his clients, and all his new ones, he kept a special set of implements that made impressive 'THWHISSSP' sounds in the air and 'THWACKs' on impact, but did almost nothing to their recipient. Soaked in red dye, they left impressive stripes on my flesh, but pained me scarcely at all. With these toys, Tom's less trustworthy clients could flog me all day without drawing a moan that I didn't fake.

Tom was safety-conscious, and really knew his clients. Those he trusted, and even favoured beginners when he had time to teach and supervise, were allowed to use authentic implements that could do real damage if they were used improperly. He kept a close eye on sessions whatever else he was doing, and ordered me (both for my safety and for the reputation of his dungeon) to use my safe words freely. He also told me not to allow clients to gag me, except with his permission, and with him standing by. Even then, as arranged between us, a rapidly clenching and opening fist or rapidly fluttering foot would cause him to halt a session.

The third reason why rough male clients didn't bother me was my own evolving taste. I came to enjoy playing the straight twink that bikers and wise guys loved to use. I could pretend that they had mastered me, and made me love them for it. As I learned 'for keeps' at Master Tom's place, I really am the pain slut that Mistress Lotte had seen in me. I was turned on by the idea of being tortured, and relished the challenge of enduring pain as long as I could stand it. Then my endorphins would kick in, and I would enter a blissful state in which the pain became unreal. Months before, Mitch had warned me about the dangers of this gift: that I could easily meet a real sadist who would do me serious harm before I used my safe word. I had been trained to stay self-conscious in scenes with all partners that I did not know and trust. I trusted Tom to ensure that my safe word - which I did choose to use sometimes - would always be respected. His tendency was always to err on the side of caution - and to halt a scene, or slow it down, before I wanted. He would intervene sometimes when I knew I was not being harmed, and when the pain felt good.

When I talked to him about this, he pointed out that he was concerned not just with what I could or wanted to take, but with safety in his dungeon, and with the attitudes and behaviours of his clients. There were other subs working or playing there, not all of them with my temperament and training; he had to be sure that everyone knew and accepted that there were limits, and that he did not want clients who failed to respect them. His clients didn't just know this automatically; he had to teach it to them, and he did this by intervening when anyone went further than he (not I) felt comfortable with. I had to acknowledge that he was right, and that I appreciated the safety that his supervision and interventions gave me.