The Pleasure Boy 19

The Pleasure Boy 19

After my trip with Nouri, the remaining months of my apprenticeship passed uneventfully. My Mom and Mistress Lotte worked well together. Their company, offering support and mentorship to lifestyle couples was now a going concern. Lisa had completed her internship with it, intending to become a mentor herself. Suzanne, too arrogant to be trainable, had been booted out. Mika and Chantal had passed the probation stage and were now full-blown apprentices, coming along nicely.

I had been Lotte's apprentice for nine months now, and the time had come to arrange for my internship doing real work under a qualified Guild master. This was no small step, because if that master liked my work and wanted to keep me around, it could lead to a paying job once I graduated. Internship for me was that master's chance to look me over and decide if I could meet their needs. Why else accept the bother of training an intern?

One evening Lotte called me to her office and waved me to the chair beside her desk. "It's time to arrange your internship," she opened. "As you know, that placement will give you a first area of specialization as a pro submissive, and could lead to a real job."

"This means that you have to make some decisions, and I have to start making phone calls. My question is, 'whom should I call?' You have to tell me what kind of work you want to do. Then I have to find someone who wants to train you to do it. When you started here, you told us you were hoping for steady, part-time work that would pay your way through university. Is that still your plan?"

"Yes, Mistress," I answered.

"Do you know where you'll be studying?"

"Yes, Mistress. I was accepted here in Montreal at McGill before I applied to you. They gave me a year's deferment. So the plan is that I start with them in September, hoping to be a journeyman by then. Or nearly one."

"Very well," she said. "That limits your choices. Most jobs for pro subs are full time. But there are two things that you could do, and my suggestion is that you try both of them. You could work as an escort and gigolo, through an agency that offers such services. You'd be arm candy for clients at particular events, and a submissive playmate (within your specified limits) for those clients who want one. That means you could accept individual short-term gigs with specific clients as your studies at university allow. You are good-looking and presentable enough that there should be no shortage of work. You'll have to arrange terms with the agency and mistress that accepts you, but at the going rates, if you take two or three clients a week, you should make enough money."

"Also, you could do occasional work at a commercial dungeon. Most of the clients at such places want to be submissive themselves. But some want to punish and humiliate a pro sub; and some want a witness and companion in their own submission. I get a few clients like that, but gay dungeons get lots of them. You would also get valuable experience as an assistant Dom. Master Thomas, one of the instructors for your Hedonic Sexuality class, might be someone to talk to. He runs a gay dungeon, and may want a whipping boy for his clients."

"Any questions?"

"Could I intern with you at HanaLot?" I asked her. "Maybe as an assistant to Lisa?"

"Lisa doesn't need an assistant yet. Your relationship with her can continue, but on your own time and hers. Also, you wouldn't get a lot of work in the dungeon here, and training lifestyle couples is not part time work. Remember what it was like with Nouri Saad? You wouldn't need to go travelling with most of our clients, but you'd have to live with them, and be available to them 24/7."

"One more thing. It's best not to intern with your training Mistress, unless there's some special need or reason for it, as there is with Lisa. If you want to end up as a mentor, you should get some experience elsewhere, and then come back to work with us when the time is right. You will be welcome here eventually, but HanaLot is not the place for you now."

"Very good Mistress. Thank you so much!"

"You're very welcome, Jim. I'll make some calls and see what I can do. When I've got some options for you, I'll let you know.

The Sunday after that conversation with Mistress Lotte, I went for dinner with my parents. As Lisa was now living them, she was present at the dinner table, when I asked my mother if she was aware of my upcoming internship, and of Lotte's decision that it should not be with them at HanaLot, their mentoring firm. "Of course, I know," Mom said. "Do you think Lotte would make a big decision about your future without my agreement?"

"We know you're interested in mentoring work, and that you and Lisa had hoped to stay together. But Lotte is right that mentoring at Hanalot is a career choice, not a part-time job. The learning curve for any work you could do with us would be the equivalent of a university course load."

"My advice is, stick to the plan. Use your geisha training to put yourself through college. Get your degree first, and then decide what you want to do with your life. At that point, you'll have more options available to you, and a better idea of who you are."

At that point, Lisa joined in. "Your Mom and Lotte haven't discussed it with me but, for what it's worth, I agree with them. I learned a lot from working with you, and I know you did as well, but it's the wrong time for commitments now. We both need to be free."

"I don't mind saying this in front of your Mom: I can still be a Dom with you, but not on a lifestyle basis. I can invite you to my bed tonight, and we can play. But I need my freedom, and you will need yours. I hereby release you from that training collar, and must ask you to release and forgive me as a Mistress."

And now my Dad spoke up: "I have no place in this conversation, but I'll give my two cents anyway. When a woman tells you that she can only give so much, your best move, if you want anything from her at all, is to take what she wants to give you and be thankful for it. You'll never improve your position, asking for more."

Mom said, "You see how wise your father is now? How much I've taught him?" He stuck his tongue out at her, and she laughed.

After dinner, in front of my parents, Lisa formally removed her tag from my collar. Then she led me to her room (the guest room) while the bed in my own old room stayed empty. We talked for awhile, and then she had me serve her - kneeling between her thighs, as if nothing had changed. And I knew that from one perspective, nothing had. Irrational as it was, I felt abandoned, though I knew that all the women in my life were taking very good care of me. My mother had passed me to Mistress Charlotte, albeit by mutual agreement and to assist in furthering my own plans. Mistress Lotte had passed me off to Lisa, admittedly to train both of us - an arrangement which had worked very well. Now Lisa, in all friendship, was claiming her own freedom, while handing me a freedom I did not want.

A few days later, Lotte spoke with me again. "I've arranged two interviews for you," she said, handing me two sheets from her notepad, with the information for each interview jotted down. "One is with Mistress Monique Allard who runs Service d'escorte Allard. She knows that you've been trained here as a professional submissive, and says that she can always use more of those in her stable if they look good and are well spoken. She's expecting a call from you to confirm the time."

"The other interview is with Master Thomas, your instructor in hedonic sexuality at Guild School. He thinks well of you, and would be happy to use you in his dungeon as a pro submissive with his gay clientele. He warned me though, that gay Doms like to play rough and asked me if you were enough of a pain slut for that kind of work. I told him that he would have to discuss that question with you. He assured me that you would be safe - that the rule about pain but no injuries applied, but that your tolerance for pain would definitely be challenged. He asked me to pass that warning on to you, and that you should give him a call if you were not frightened off."

"I've made a few other calls, but those two are your best bet for short gigs in Montreal, consistent with a full course load at McGill. Best of all, they are also mutually compatible. As school work allows, you could accept or decline assignments from both of them, while both would understand when you turned them down. Also, for the time required, both of them would pay well - the gigs with Mistress Monique because classy escort work is lucrative if clients want you; those with master Thomas because he'd charge plenty for what his customers want to do to you. It would be up to you to specify your limits."

"So there you are," she ended. "Call those numbers, talk to both of them, and let me know what you want to do. I say again: I think those are your best options in Montreal right now. There's plenty of work for pro subs elsewhere, if you forget about McGill."

On that note, she dismissed me. I went to a public phone in the lounge and arranged to meet with Mistress Monique next day, and with Master Thomas the day after. I didn't want to forget about McGill. And I wanted to stay in Montreal, near my family and Lisa.

Mistress Monique Allard turned out to be an attractive woman in her early forties when I met her that Wednesday afternoon. The Allard Escort Service had been founded by her parents who were still around, but largely retired. Monique was now its effective manager. Once she'd established that I was completely bilingual, speaking both French and English (the two official languages of Canada) without an accent, we spoke mainly in French - the main language of most of the firm's clients.

"BDSM is by no means our main business," she explained. "Only 63% of our customers want any kind of sex from the escorts that we provide. The main requirement is that our staff must be socially presentable - well-dressed, well-spoken, good to be with and be seen with. Clients who just want the BDSM would probably go to a commercial dungeon - like that of your Mistress Charlotte. Still, you might be surprised how many wealthy, powerful people want good sex or good kink after some meeting or conference, someone whom they can take to a fine hotel without embarrassment. Someone they can share with, and show off to their friends. We do a good business - with a stable of young men and women with proper geisha training."

"After your internship, if you join our stable as a journeyman you could expect to be offered a gig for an afternoon or evening or both, two or three times a week. You wouldn't have to accept them all. You could choose just the ones you wanted and had time for. I understand that you will also be going to school during the internship and after - doing history at McGill, Lotte told me. That's actually a bonus for us. It means you'll be equipped to keep up your end of a conversation, if you also follow current events. Depending on the service provided, you'd bring us at least $600 for each hour of your time (because that's our minimum for people like you), and you'd get half of that, because we keep the other half for finding, screening and doing business and making arrangements with your client, and for keeping you safe. So for a three-hour 'date' - less than half a day's work - you'd make $900 dollars. Not bad for a kid just entering college!"

She went on, talking about the screening, pricing and safety arrangements, to convince me that they'd be earning their portion of my fee. I'd learned about such agencies in Guild School - and how to tell the good ones from the rip-off artists. I knew that agencies like this one were worth the percentage they took.

In the end, Monique offered me a contract which, I told her, I would accept, subject to Mistress Charlotte's approval. She agreed this was only proper as I was still Mistress Charlotte's apprentice. We shook hands and I thanked her for seeing me and for the job offer. I left, pleasantly surprised at how much money I would be making for so little of my time.

I now understood why my mother had suggested geisha training as a way to pay for my education. At the same time I wondered that she had done so. In effect, she had seen me as - or turned me into - a gigolo, a high-class male prostitute. I knew by now that I could accept that identity and even be proud of it. I had been trained so by experts who shared it, whom I admired greatly. At the same time I understood why most people, without my training, would judge me with contempt; I understood why my high-school girlfriend Kendra had wanted no part of it.

My interview with Master Thomas went rather differently as we already knew each other well from his class at Guild school. He greeted me cordially, and began by congratulating me on having reached the stage of internship. "In two more months you'll be a journeyman," he told me. "I know you'll graduate with honours. Everyone at the School thinks well of you, and your trainer, Mistress Charlotte sends you to me with a glowing recommendation."

"What I don't understand," he continued, "is why you're coming to me. The point of internship is to set you on a path for your career as a geisho. I know you're not gay, and I don't see you spending much time in commercial dungeons as a kinky rent-boy. You could easily do your internship as someone's companion, assistant or private secretary - all with benefits, of course. So why intern with me?"

I told him that I was looking for part-time work to pay my way through university, had already been accepted by McGill, and wanted to stay in Montreal.

"Ah, I see," he said. "Now I get it. Lotte should have explained your situation on the phone."

"Look, here's the thing. If you want, I'll let you give it a try, but gay BDSM gets pretty heavy sometimes, and if you show the slightest disgust or reluctance with a client, unless he's actually abusing you, I'll have to let you go."

"As a twinky youth, you'll be in big demand, especially if we get rid of your body hair, and dress you for the part. A sexy, submissive twink is just what you are; that won't need any acting. Daddy-types like me will eat you up. To be frank, I'm salivating right now at the prospect of giving you an audition. I know you can hack it. If you trained with Lotte, Mitch (a good friend of mine, by the way) will have had his way with you more times than you have fingers and toes. But if you can't show your client that you actively enjoy it, it isn't going to work."

"I don't mean that you have to enjoy all clients equally. Nobody does. I can protect from real slobs to some extent. But once you have a client, you'll have to be completely professional. You can't ever show disgust. You have to convince the guy that the sex, at least, if not the man himself, is turning you on. Unless he's actually abusing you, in which case, it's my job to spot it and call him off. And you'll never be penalized for using your safe word, when there's real need."

"I understand, sir. I think I can do the work as you describe it - with those conditions, I mean. Though I'm hetero by nature, I've learned to enjoy gay sex, not just accept it. I'll be happy to do that audition if you want me, and if I don't please you, you won't need to try me with paying clients."

"That's a deal, Jim. I couldn't play with you while you were in my class; but if you offer yourself now, I have no reason to turn you down. Just let me lock up first, so no one can walk in on us. While I do that, I want you to strip and take a pose that offers the use of your body. Show me how you would do that."

He left the room. I undressed quickly, folded my clothes neatly in one corner, then looked around for ideas. Realizing that just bending over his desk would present my bare buns nicely, I draped myself across it, gripped the far side and spread my legs wide so that my rosebud was on view and only my toes touched the floor. Then I relaxed, breathed slowly and deeply as I'd been taught, and put myself into the mindset of a sex toy waiting to be used.

In a short while, Thomas came back and found me in that position. "Well, well," he said. "What have we here?" He came up behind me, caressed my ass cheeks and then began to spank them - lightly, sensuously, at first, then harder till each smack gave a lovely sting. Next he stroked between the cheeks, fondled my balls and diddled the gaping hole with his thumb without quite entering me yet. Reaching under me, he found that my cock was already hard, so he grasped it, pulled it back and down between my legs, and stroked it firmly till I was almost ready to cum. Then he stopped, and began to whisper caressingly, "You're doing fine, Jim. For a boy who isn't gay, you're faking it real good. You're giving me a treat!"

"I'm faking nothing, Master," I answered him. "I'm submitting to you and enjoying it. That's what I've been trained for."

"Please use me for your pleasure, Master! Please fuck me if that pleases you! I'm here for you to use as you see fit."

He rolled a condom onto his cock, lubed us up and took me up my chute while I steadied myself on my forearms and pushed back against his thrusts. His prick was long, though not quite as thick as Mitch's, and I felt well impaled and taken as he fucked me - gently at first, but more firmly as he built the tempo, ramming my ass cheeks with his body as he came.

Afterwards, he stood me on my feet, turned me around and had me roll the condom off him and dispose of it, then lick his shaft and balls to clean him properly. "Now it's your turn," he said.

He had me sit on his desk, leaning back on my forearms with my thighs spread wide, offering my own cock for him to suckle. "Don't cum without permission," he said. "My mouth will be full, so I'll reach around and tap your back twice to give it."

Then he diddled me by hand till my erection was painful, then took me down his throat and bobbed his head on my shaft, more easily than I thought possible. At last he tapped me and I came. He pulled back as I climaxed, so that most of my seed remained in his mouth. Then resting for a moment, he stood up and kissed me deeply, giving it back to me. I smiled at him, swallowed my cum, and licked my lips as I'd been taught to show appreciation for his efforts.

"All right," he said, adjusting his clothes and motioning me to get dressed, "Thank you. That was excellent."

"You may not be gay by nature, but no one would know it. You obviously enjoy gay sex. I'd like to see how you take punishment, but we can do that some other time. As a pupil of Mitch and Lotte, I'm sure you can take as much as I would let anyone give you."

"If you play the part of a straight, bi-curious youth looking for some experience with the same sex, you'll be a hit with some of my customers. You'll just need to fumble a bit - show them less experience and skill than I can see you have."

Then we talked business for a while. Unlike Monique, who would offer me gigs as she had clients, Thomas wanted me to commit to regular hours. "At university, you won't have classes on weekends," he said. "How about if you come in here on Friday, Saturday and Sunday for a four hour shift in the afternoon or evening. Would that work for you? Those are my busy times. I would pay you an hourly rate."

I explained about my escort work with the Allard studio, and about study for exams; and we agreed that I would start out working 12 hours a week for him on Friday evenings and Saturday and Sunday afternoon or evening as he preferred. "But that may be more than I can handle," I told him, "and I may not always be able to make it. Unless I'm sick or there's an emergency, I'll be able to give a day's notice, so you'll have time to arrange a replacement when I can't do my shift. Also, if 12 hours a week is too much, I may have to cut back. Can we start like that, and see how it goes?"