The Pleasure Boy 25

The Pleasure Boy 25

Settling into my new home with Mistress Natasha felt like a whole new start to our relationship and to my D/s career. It was the first time I'd ever served as a houseboy, seeing to my Domme's domestic pleasure and comfort on a regular basis. As I had a full schedule with other duties, it took my Mistress a few weeks to work out a regimen of chores and responsibilities that would significantly lighten her own workload while leaving me sufficient time for escort work and study. We started out having me do all the tidying, cleaning and laundry, as well as shopping and cooking, just to see how long these chores took me, but soon found that they were far too much. Working as efficiently as I could, it was soon clear to both of us that a full list of household duties did not leave me nearly enough time to attend lectures and study sufficiently, never mind serve the professor as a research assistant, or do my escort work. Eventually, we agreed that I would do the shopping and cooking (which Natasha hated), but that she would do the laundry and ironing for both of us. I would supervise her existing house cleaning service which came in once a week - which I could do while I was studying or writing, or editing Sorkin's work. We would tidy our own rooms, but I would make Natasha's bed while she was getting dressed and doing her makeup. We would shower together and I would wash her, but she would help me also. I would get up half an hour before her to shave and do my other morning business before making the coffee and laying out a simple breakfast, before waking my Mistress and joining her at the table when she was ready to eat.

Living together now, we found a new level of intimacy, with its own pleasures and problems. On one hand, we had much more opportunity to play sex games and explore each other's bodies. With a bed pet available almost every evening, Natasha's sexual desires became more varied and voracious, and she became increasingly proficient with the BDSM implements that I helped her choose and buy. But with so much time together, and so closely involved in each other's affairs, I sometimes got on her nerves. (She would have gotten on mine too, if subs were allowed to have any.) We soon took up my mother's suggestion that I keep myself scarce and stay out of Natasha's way, unless I was summoned or had a specific chore to do. In theory, I was not even allowed to speak to her unless she spoke first; but my Mistress never enforced this rule if I used good judgment in respecting her needs for solitude and privacy. I soon learned when she was safe to approach and when she preferred to be left alone.

As a novice Domme, she had a lot to learn about the uses of corporal punishment and she had the usual, healthy inhibitions about her own natural sadism. But when I displeased her in any way, she learned to punish appropriately and wisely - using her hairbrush, strap or cane, in ways that no sub would look forward to. With my training, I feared her displeasure more than the pain of corporal punishment. But as her instructor in this skill, I was surprised and pleased how quickly learned the uses of CP as a means of intimate communication. When she punished me, I usually deserved it in some way; but not always. Though she kept her streak of sadism well under control, she would indulge it sometimes - sometimes as foreplay for sex, sometimes just to remind us both of her prerogative in a D/s relationship. For my part, I encouraged her in doing so - not out of masochism, but to prepare her for other subs in the future. She had to learn that many subs would not be satisfied or would not learn to trust a Domme who lacked the confidence to impose regular discipline when they felt like it, just because they could do so.

As I grew accustomed to dealing with this same woman in two different ways: sometimes as Professor Sorkin who had sponsored me as a graduate student, and sometimes as my apprentice Mistress Natasha, so she grew accustomed to several ways of dealing with me. Sometimes I was Mr. Woodruff, her student at the university; sometimes I was her houseboy and sex pet Jim. And sometimes, to help her learn the skills and attitudes of a Dominant, I had to be her instructor. I had to teach her to be strict and demanding as a Mistress, but also generous and fair. And gradually, she took to this role, learning to get pleasure and useful work from a sub within the terms of a contract, and to keep that sub happy and eager to serve. She gained skill in giving precise orders, and in giving appropriate punishment when she did not get exactly what she wanted.

In sum, as I helped her learn the skills of a Dominant, I myself learned that just sharing a home with someone - never mind as a professional submissive or a domestic servant - was an education in itself. I found that living together took all the patience and skill that had been trained into me, and that domestic life had its surprises - that my training was not always enough.

With a trained submissive at her beck and call, Mistress Natasha's sexual appetites burgeoned and diversified. She came to want sexual satisfaction more often, and in more different ways. At first, she sent for me once a week - on the Friday nights which I kept free for her. Well before I moved in with her, she was summoning me several times a week, and trying to keep me around on weekends, when I had escort assignments. Busy with those or with my school work, I would turn her down - which irritated her, and which I never liked to do. We had to put my visits on a schedule - one that I could not always keep.

Once I'd moved in with her, sex was easier, When I was home, she could get quickies almost any time she wanted them. Unless she saw that I was busy studying, she did not hesitate to ask, and she might do so several times a day. Except for weekends, when I was often booked for escort assignments, she could get as much sex as she liked. Usually, she had me serve her every night, often with whole evenings devoted to her pleasure.

What with classes, tutorials and library work, I did a lot of running around on week days. So as not to waste time dressing and undressing, she allowed me to wear clothing during the day. Evenings, however, except if I was going out later, I was required to 'undress for dinner.' Then, because she liked to see me that way, I would serve dinner and come to table wearing only collar - and would remain so until I dressed next morning. Sometimes, when her evening's sport was tease-and-denial, she'd instruct me to cage my penis when I stripped for dinner. Neither of us had any interest in my chastity for its own sake, but I taught her to frustrate me often, just to remind her sub that he was to get his pleasure from serving hers, and be grateful for anything she allowed him for himself.

As I lived with Mistress Natasha, I gradually became familiar with her tastes. There were things that she taught me, and a few that I discovered by myself. One thing she bluntly told me was that she had little interest in the missionary position, or in ordinary, cock-in-vagina fucking. When she wanted to feel the male thrusting into her, she preferred to be mounted from behind so that she could meet each plunge by pushing back against it. Sometimes, she liked to kneel astride my hips and ride my cock. Occasionally, she'd allow me a missionary, face-to-face fuck as a special reward. But for her, bread-and-buttter sex meant cunnilingus: stimulation of her pussy lips, clitoris and love tunnel by my lips and tongue. She also loved to have me kiss and lick her anus, and penetrate it lightly with finger or tongue. Often, she liked to cuff my hands behind my back and have me serve her with my mouth alone. She loved what she called 'lip service' - oral sex in all its forms, even when used as a reward or tease for me.

After serving her in this way, I would sometimes be refused any release of my own. She did not need a cock cage for this purpose. She knew I would not masturbate or cum without permission. But she loved to watch me masturbate and learned to guide my masturbation - having me perform for her viewing pleasure, and edging me to delay by climax or leave me in frustration.

One game I taught her, called 'the doggy fuck,' (first used on me at Mistress Lotte's by a more senior apprentice), Natasha came to love as a deliciously humiliating reward to use when she was specially pleased with me. I would sometimes be required to present myself - nude, of course - on my hands and knees, with my head up, my spine arched downward and my bum pleasingly presented as if for pegging or caning. With me in this position, she would sit or kneel beside me, having lubed her hands in preparation. First she would have me wag my butt and formally ask for the privilege of using her hand to masturbate myself. She might make me beg for awhile, but eventually she would grip my cock loosely with her right hand and order me to come to full erection by thrusting my hips so that I stroked its head on the slippy palm of her stationary hand. Basically, it was a hand job in which I did all the work. In the posture of a mounting dog, I would be allowed to stimulate myself till I eventually came. Then she would gently wipe her hand on my face, have me lick it clean and thank her for the pri­vilege that she had granted me. Then she might ask if I were not ashamed for needing to relieve myself in this fashion, and thankful that she had graciously allowed me to do it!

The doggy fuck could easily be turned into an edging game by having me beg to cum when I was close to it and then be required to halt for awhile and wag my bum slowly till I cooled down. Mistress usually augmented the stimulation by fingering my ass hole with her left index finger as I worked myself on her other hand, but sometimes she would use her hairbrush or a leather paddle to spank me instead. She might require me to bark or whine - "make doggy sounds" - while I used her hand in this way, and think of myself as horny farm dog, put to a bitch for breeding.

Through this and other such games, I introduced my Mistress to the concept of 'erotic humiliation' - the fact that for many people the animality and neediness of sex is a big part of its appeal. For many others, unfortunately, it puts them off of sexual expression as disgraceful, subhumanly beneath them. But one big gift of D/s - and of BDSM, in general - is the permission it offers to put that attitude aside, and indulge with a trusted partner. We think of this mostly as one payoff for the submissive, but the Dominant gets it in a different way, as an indulgence in sexual selfishness.

After I bought her a deluxe pegging kit, Natasha also came to love the male role in sexual connection. With practice she became expert at taking me up the ass, either face-to-face (with her on top and my legs up on her shoulders) or from by mounting me from behind. The kit, which came with multiple dildos of varying shape, length and thickness for stretching me, also had a large vibrating knob for her vagina, which she usually kept turned off as too distracting. With skilful use, she could bring me to climax through stimulation of my prostate gland, while at the same time, bringing herself as well, just as man would with a passive lover. With this artificial penis, she loved sometimes to take the aggressive, masculine role in our sex life, subjugating me to her pleasure as men had done so often with her.

The Velvet Dungeon

Just once, wearing a mask so she could not be recognized, she let me take her to a BDSM club in another city. I had already taken her to a munch in Montreal. I believed she needed to know that there were such places, where she could meet, talk and play with subs and fellow Dominants.

At the play club, nude except for my cock cage and collar, I walked around behind her on a leash and knelt at her feet when she sat down. Several people came over to her, ignored me, but asked where she was from. She was coolly polite, declined to play with anyone, and told them nothing at all about us. They soon lost interest and left her alone. She just watched the play and the costumes like an anthropologist on a strange planet with weird life forms.

Later she told me that public play with strangers did not interest her and might be dangerous for her reputation. What she did with friends in private could not harm her, she said, even if it became public knowledge. But play at clubs like this one were another story. For my part, I wanted her to learn from other Dominants and get experience with other subs, but it was clearly her decision to make. Now that she knew there were such clubs in most big cities, she could find them for herself if she ever wanted to.

She enjoyed that evening, however, and so did I. At one point, a shibari master visiting from Japan asked her if he could use me as a subject for his demonstration. He already had a lovely female sub in tow, and said that he was going to show how two subs could be bound together either to pleasure or torment each other. Natasha looked at me for a cue, and I nodded. The man sounded like he knew what he was doing, and I wanted to learn more about rope work, having gotten little of it at Guild school, or in my training at Lotte's.

So Natasha removed my cock cage as Yamaguchi sensei requested, and gave me permission to cum if - as he was claiming - he could make me do so from the bondage alone, without stroking me or letting anyone else do so. Then he led this other sub and I to a raised platform round which his audience was already gathered. First, by assigned pet names, he introduced his subjects to the audience, asking if we consented to be roped together under the stringent safety conditions which he explained to everyone. Then, stressing artistry and medical safety, he proceeded to give a talk showing how two subs could be bound together in such a way that they could not help giving each other either pleasure or pain, depending on some details of how they were tied. With two silk handkerchiefs, one wrapped around my penis, the other twisted to pass between the lips of his female subject's vulva, he proceeded to tie us both in such a way that we were bound together, but in such a way that our writhing would cause those handkerchiefs to rub our organs. With the lubricated silken fabric that he would use now, his helpless subjects would give each other pleasure and might climax eventually. With a rough fabric, anointed with Tiger Balm or Icy Hot, the same bondage would be torture. Either way, we could not keep the fabric rubbing each other's genitals no matter how we tried not to move.

The Master did not know that I'd been trained in orgasm control; and I could easily have spoiled his show if I had wanted to. But I'd been given permission to climax, and had no reason not to play along, enjoy myself and do my best to assist his performance. I just relaxed, gave myself to the situation, and let the silken fabric bring me first to a stiff erection and then to orgasm, while the ropes binding me to 'Lotus flower,' his female subject, ensured that my movement did the same for her. Between us, the ropes made a feedback loop of reciprocal stimulation. We came almost simultaneously, and the audience applauded all three of us.

In my first year of living with Natasha, my mother took her role of mentor very seriously. She asked my Mistress to keep a diary of our relationship - mentioning any area of dissatisfaction - and to ensure that my punishment book was properly kept and reported for review and appropriate action. For her part, Natasha learned to be a strict but fair disciplinarian, to trust that my mother would not favour me in disciplinary matters (as I had known she wouldn't), and to rely on my Mom and HanaLot for impartial support in her role as Domme and every aspect of our contract.

Permission to maintain close personal ties without supervision was written into my contract with Natasha; but Mom gave my Mistress a standing invitation to accompany me whenever she had me to dinner. Most of the time, Natasha did so; and the two of them got to be friendly. But now and then, when Natasha was busy with something else and couldn't join us, I had the chance to speak with my mother in private. On one such evening, we had a conversation that became important for the future.

It began when Mom asked me point blank, "Do you love her?," meaning Natasha Sorkin, of course.

"To be honest, I don't Mom," I answered. "Not in the sense I think you mean."

"I respect her greatly as a scholar and teacher, and I'm learning a lot from her. As a long-term client, I'm attracted to her. Serving her and helping her learn to Dominate is no strain at all. She has the character for it, and she's coming along nicely. So is my work as her grad student. Our quid-pro-quo is working well. But if you're asking what I think you are: 'Do I see her as a life-partner like you and dad or Lotte and Mitch?,' then the answer is no. Our contract expires when I get my degree. I might agree to renew it for some post-doc work - maybe, to help her research and write a book. As I said, I enjoy serving her, both sexually and academically, and I'm learning a lot. But I don't see this contract as my whole life. When the time comes, I hope to go on to something else."

"In the academic world?" my mother asked.

"Maybe," I answered, "but not necessarily. "I've got the beginning of one career as a geisho and of another as a historian. Where I want to go with them, I don't yet know."

"It's too soon to think about it. I love my life as a geisho, a professional submissive. You really got my number when you tested me back then - before you sent me to Mistress Lotte for training. What the academic world will offer me, I don't yet know. I'll have a better idea when my thesis is finished and I see what kind of reception it gets, what the job market is like in my field."

"You're right," Mom said. "It's too soon to make career plans; but if you don't love your Mistress Natasha enough to make a life with her, you're going to have a problem with her eventually. Because she's in love with you. When this contract is up, she'll want you to marry her and make a life with her."

"How do you know that? Has she said something to you?"

"She didn't have to. I can read the signs. You've taught her to be a Mistress. Specifically, you've taught her to be your Mistress, and she likes the arrangement. She won't let you go easily. She'll try to keep you around."

"Well, if I want to, I'll stay around. I don't need to love her. I could probably make a fine academic career as her assistant and sidekick."

"True," my mother said, "and that's what she has planned for you. If you want that career, it won't matter that you're not in love with her. You'll serve her faithfully and well, and she may not notice the difference. But if you want out for some reason, it may not be so easy. You might want to start preparing her. Get her to understand that you're not going to marry her; that you're just a good geisho fulfilling a contract, and that she'll need to find someone else in the long run."

"Thanks for the warning, Mom," I said. "I'll think about it. Cooling her down might not be so easy right now. I haven't even started writing a thesis. Until that's done and successfully defended, I need her much more than she needs me. Once I get my doctorate we'll be on equal terms. That will be the time to rework our contract for the long-term."

Mom said no more, but I could tell she was still worried. Thinking about it, I could understand why. She was right. My client was falling in love with me. As her subordinate, working with her in her own highly specialized field, I was becoming very useful to her. It would not be so easy for her to find a replacement for my services. She might well do her utmost to keep me around. She could make an academic career difficult for me, if I tried to leave her.