The Pleasure Boy 08 – BDSM – Free Sex Story

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That morning, Mitch showered with me, having us do a thorough job on each other to lose the scent of our last night’s activities. After we shaved and groomed ourselves he checked me over and had me do the same for him, informing me that geishi often help each other in this way. “We must look (and smell) good enough to eat,” he told me. “The pun is intentional. It’s a signal of competence, and part of our profession. For an important occasion we can’t trust our own judgment, because there are parts of our bodies that we can’t see or get close enough to smell; and because we’re so used to our own appearance and body odour that we don’t notice them any more. The other apprentices will be asking you to help them in this way, and you must do the same. While you are with us, ask for help with your grooming every morning, so that it becomes a habit. You will get entries in your punishment book, if Mistress or I find fault with your self-presentation.”

We went to breakfast. “You don’t have school yet,” he told me, “until you do, you’ll spend half your day helping others with their assignments. Be sure to check the schedule sheet on the wall there,” he added, pointing. When I went and looked, I saw that Mitch was down for house chores that morning, and that I was scheduled to help him. There was also a name on the sheet that I did not recognize. It had a line through it.

“Who is Rose Baltich?” I asked him. “There’s no one here by that name.”

“She’s a woman from our cleaning service,” he answered. “She comes and helps us twice a week, so that we don’t have to do it all ourselves. It would be a poor use of our time. We cancelled her for today. “

“Why do we do any cleaning then? You could have the service do all of it.”

“It’s part of your training,” he told me. “Today, I’m taking her place, to work with you, get you started and teach you. In future, when you’re on cleaning duty, you’ll be working with her or with one of the other apprentices.”

“You’ll notice that only some of the rooms have tick marks next to them. Those are the ones we’ll do today.” Later I learned that the washrooms, the kitchen and the dungeon were cleaned daily, and that other rooms were cleaned every third day. Of course, the apprentices were required to keep their own rooms neat.

That morning, Mitch took me around the training house doing chores. He pointed out the closet with the cleaning equipment, and showed me what was required in the kitchen and washrooms. I would do those rooms while he went and cleaned his and Mistress Lotte’s bedroom, where I’d been a guest last night. He told me to do the kitchens first, and then come down and help him with the dungeon when I had finished the washrooms. The last thing he said was, “The work has to be done, but it’s not the work itself that is important. It’s your attitude in doing it that we care about. Remember that you’re here to learn pleasure.” Then he left me to work alone.

I had no issue cleaning the washrooms. I could buckle down and do chores when I had to. I could even work cheerfully, without feeling bored or annoyed. What left me frustrated was that last speech about learning pleasure. Mistress Lotte had said something like that, about taking pleasure in service. For that matter, I had heard my mom tell me much the same thing. As an ideal, I could see it — but feeling actual pleasure in wiping out the toilet bowls was another story. That was beyond me.

But here it was expected of me; and I had no idea how to pull it off. “Never mind for now,” I told myself. “I’ll ask someone about it later.” The old saying, ‘Fake it till you make it,’ came to me. If I could pretend to be enjoying this work — and that was easy — my trainers would be satisfied, and maybe the pleasure would come.

In this way, I got the washrooms cleaned; and Mitch, when he came back, told me that I had done a good job, except for two spots that I had missed in one of the showers. Then he sent me off to get some lunch, and spend the afternoon studying.

After a light meal of bread, cheese and soup, I went back to my room, and got on with the introductory reading. The Epicureans and their Adversaries was the chapter’s title. Epicurus was a Greek philosopher born in the 3rd century BC who made enemies with his teaching that the central goal and purpose of human life was happiness. The chapter explained that as geishi, we agreed with him, going on to explore (and teach) the role of pleasure in a happy life.

When people think of ‘pleasure,’ they tend to think first of sensual pleasure — compulsively over-indulged in, to boot. But Epicurus, the founder of serious pleasure-philosophy taught no such thing. What he proposed was a philosophical theory of ‘the Good Life,’ based on sustainable pleasure and freedom from fear and pain. For him, these were the soul’s only intrinsic goods — goods that we pursue for their own sake. A thorough-going secularist, he rejected the notion of gods and an after-life, asserting that this life and happiness in it was all there is. He did not claim (and neither do geishi) that pleasure is the only component of happiness. He would accept, as we do, that we don’t just want to have good experiences; we want to be good people and do good things. But he asked his followers to accept that in the last reckoning, we ourselves are our only judges of what is good — not the gods, not the state and its authorities, and not our friends and neighbours.

The chapter continued: It’s not hard to see why Epicurus made enemies — nor, for the same reasons, why people are suspicious of geishi and of pleasure itself. The fear is that pleasure is addictive and distracting: that it will divert people from serving the gods or the state or one’s own social commitments, and from perceiving and avoiding real dangers and threats. Moreover, there is a valid argument that happiness itself is paradoxical, in that the direct pursuit of it is self-defeating. The experience has been that persons who go after happiness itself are perpetually frustrated. The happy people are those who forget themselves and their happiness through their engagement in pleasurable and worthwhile activities. This was the first part of the introductory chapter in a nutshell.

The second part acknowledged the concerns as valid, but went on with the geisha response: The book agreed that happiness is paradoxical and best pursued indirectly through loving engagements and commitments. It introduced Csíkszentmihályi’s concept of ‘flow’ — absorption in one’s present activity and situation — as an ideal mental state. It conceded that pleasure can indeed be distracting and addictive — a point that Epicurus himself was well aware of. It must therefore be treated not as an enemy, but as a somewhat dangerous friend: pursued with moderation and wisdom, and with an eye on the long-term. No one thinks that neglect of necessary duties and chores will bring pleasure in the long run.

For that very reason, the text continued, our pleasures need to be be chosen and indulged with wisdom. For that very reason, the geishi with their experience of mindful pleasure have something worthwhile to teach. Agreeing with the epicureans that only happiness and pleasure (broadly and wisely understood) can be valid ends in themselves — that other values and goals are instrumental to happiness — it concluded that pleasure is a test of authenticity: If you don’t feel good about what you’re doing (at least, better than you would feel not doing it), something is wrong.

The introductory chapter concluded with a statement of the underlying rationale and goals of geisha training:

• to become a connoisseur of pleasure — to sample and experience the range of safe and meaningful pleasures, so as to distinguish intelligently between pleasures which conduce to long-term happiness, and empty or self-defeating pleasures which do not;

• to make a profession of being pleasurable — someone who contri­butes to the occasion, and makes it a better experience for others;

• to choose and study some worthwhile pleasure as a specialty that one can teach and distribute with others.

In short, the trained geisha (or geisho) will be a credit to our profession and to the idea of pleasure itself. By helping others to live pleasurably and being pleasant to have around, she will earn her fee and bring credit to the Guild and to her trainers.

I wondered about my mother, and Mistress Lotte and Mitch. I wondered about the training I was getting — about the profession I was getting into. Did they live up to this standard? I wondered they did. Could I? I didn’t know yet. Only with time and training would I understand. I looked at the digital clock and saw it was almost time for dinner. I went to pee (a great pleasure when you have a full bladder), then washed my hands and went to table.

As we finished eating, I saw Joe, Gayle and Lisa look at each other and then at me. I could tell they were up to something. When they invited me to go to the dungeon with them, I tried to decline, but Mistress told me to go with them. “Good that you see it coming,” she said, “but think of it as an initiation rite. You got part of it last night from Mitch and me. You’ll get the rest of it tonight from them. After that, if they accept you, you’ll be one of us.”

I didn’t miss the implication — that if my fellows didn’t like me, I’d be gone. But I saw the justice of what was happening. These other apprentices and people like them would eventually be my colleagues. Just now, as more advanced apprentices, they were among my teachers. I needed their acceptance and good will and would have to pay its price, whatever that was. “I understand, Mistress,” I answered her, and turned and went with them.

In the dungeon, Lisa took charge. “You’re here to learn about pleasure,” she told me. “You can start by giving us some. If you please us we’ll welcome you and teach you. If you refuse us, we’ll turn away from you. Then Mistress will notice and you won’t last long as her apprentice.”

“Why do you put it as a threat?” I asked her. “You all are senior to me, and you’ve been nothing but welcoming since I arrived here. And you heard Mistress tell me to submit to you. No more was needed. It will be my pleasure to pleasure you.”

“Very well,” Lisa said. “We’re going to play make-believe. We’ll start with Joe here. “Tonight, he’s an obnoxious prick and you’re to serve him. You’re his rent-boy, paid to suck him off. Gayle and I will watch to see how well you do. Then Gayle wants to have you worship her, and I am gonna peg you — this first time with a very slim, well-lubricated dildo, as I know your rosebud hasn’t been prepared.”

“Now offer yourself like a good slave boy and let us have our way with you!”

Closing my eyes, and taking a moment to get into role, I turned and dropped to my knees before Joe, giving him my best obsequious smile. “I’m here to serve you master,” I said. Then I bowed down and kissed his foot. He grabbed my hair and roughly pulled me up to an erect kneeling posture, then thrust his drooping cock into my face. “There you are boy,” he ordered. “That big guy needs a good blow-job. Show him what you can do.”

I’d watched all those Porn films when my mom was testing me, and had already sucked cock once before, for Mitch after his sexy spanking. Now I resolved to play my part — to give him, and my future customers, their money’s worth. In this mindset, I went to work.

As I sucked him, Joe made a start on teaching me deep throat. When he came, he made me hold his seed in my mouth and taste it thoroughly before I was allowed to swallow. Then he had me lick him clean, kiss his cock and thank him for his gift. “Thank you, sir,” I said, and found that I meant it. He was testing me and teaching me, and I knew he had had better blowjobs than I could give him at that point. He could have been much rougher with me if he’d wanted.

Next, Gayle presented herself. Bowing down to her, touching my forehead to her foot, I set myself to imagine her as an incarnation of womanhood, standing in for the Goddess to receive the male’s devotion. With my lips and tongue, I paid tribute to every part of her, keeping my hands away as if I was not worthy to touch. Thinking of my mother, but also of Mistress Lotte, my girlfriend Kendra and Gayle herself, all represented in this one female body, worship felt very natural. In a small way, I could make pleasuring her a religious act.

I found her clit (Kendra had taught me where it was and what it was for), and licked with devotion. In a few minutes, Gayle climaxed. “Not bad for a beginner,” she said.

Last, I knelt on the bed and held my bum cheeks apart for Lisa’s entry. Her tool was thin as she had promised, she had lubed it well, and I was surprised at how easily it went in . . . and at how good it felt as she fucked me with it. I was surprise too at how submissive this made me feel, and at how much I was enjoying this abject submission. I had a flash of insight on how I would resent this submission — or how a woman might — if I did not enjoy it. Before long, I had a big erection which Gayle noticed. She came over and held my cock in her fist, as Lisa pumped away at me. The strap-on Lisa was using had a part that filled her Pussy — so that as she took me, she was stimulating herself. After she climaxed, she asked me if I wanted to cum. “Very much, please, miss,” I answered. The two women exchanged glances.

“Hold him loosely now,” Lisa said to Gayle, “so that he can slide in and out. Here’s some lube. We’ll have him fuck your hand.”

Then she slapped my bum, making me lurch forward. “Go on,” she told me, “do it. If you want to cum, that’s how it will be. Fuck Gayle’s hand. We want to watch you do it.”

I thrust my hips forward and then pulled back, feeling the sensitive tip of my penis slide through Gayle’s loosely gripping fist. I did it again, and then again. At some point it all changed — from a voluntary motion that I was making because I’d been told to, to the instinctive rutting that takes over males completely. Feeling that I was close to cuming, Lisa grabbed my hips and held me, making me pause for a moment till I was under control. Then she pushed to start me moving again, warning me not to cum without permission. Several times she led me through that cycle, until she had me begging. “Please let me cum now,” I moaned to her. “I’m gonna cum in a moment even if you’re holding me.

“Not yet,” she answered. “Control yourself. A man must not cum until his woman is ready. And we’re not tired of watching you yet.”

She pulled me back against her so that I couldn’t move. Somehow, for that moment, I managed to suppress the mounting climax though the wondered of the exhibition I was giving made me even hornier. But when Lisa released me, thinking enough time had passed, I pumped just once before exploding in Gayle’s hand.

Gayle contrived to catch most of my semen, and when I stopped moving, she held her palm under my nose and had me lick it clean. Then, like a wrestler, she held me in that same submissive posture — Ass up, nose in the mattress — while Lisa spanked me, longer and harder than I expected. “That was bad,” she said. “You came without permission. You’ll be punished severely if you lose control when Mistress Charlotte uses you.”

“Better believe it!” Joe put in. “I came here thinking that men take women and that women give themselves, or allow themselves to be taken. With enough pegging and punishment, Mistress managed to teach me that either Sex can do the taking, and that it actually works better for both sexes if we men give ourselves and leave control to our women. Their arousal tends to be slower than ours, and they can cum repeatedly while we need time to reload before we can cum again. If the timing is up to us, they are left dissatisfied. If it’s up to them — if it’s understood that their pleasure is the male’s responsibility before we take pleasure for ourselves — they have more fun, and we get more and better fucking.”

Soon after, we said goodnight and went to our separate rooms. Gayle and Joe had college next day, and Lisa had a paper to finish. I wanted to talk more, but the others didn’t want to stay up late. So I found myself alone, still wide awake and thinking how far I’d come, sexually speaking, in just the last few days.

Before my father’s remark at the dinner table, I was a typical young man, 18 year old, with an 18-year-old’s sexual experience. Perhaps I was a little more introspective and book-smart than most, but in general I was a pretty typical kid. I had a girlfriend just my own age. Her parents accepted me. They knew we’d gone on dates and (presumably) groped each in a typical teen-age way. They didn’t know we’d gone all the way a few times. If they knew, they might be angry, but wouldn’t be too surprised. A week ago, that was the sum total of my experience. Now I was in a different ball-park altogether, I wondered, — chuckling to myself at the play on words.

It wasn’t that I knew so very much now, or that I’d had so much experience. I’d only had a few days worth. But I’d been exposed to a pornographic encyclopedia of possibilities, and had a smidgen of experience with a few of them. I’d learned how ignorant I was — how much I still had to learn to even start to compare with the people I’d just met. I’d also come to see my mother in a new way — as the colleague, peer and friend of Mistress Lotte, with the equivalent of a PhD in kinky Sex.

I thought where all this left me with my girlfriend Kendra, and couldn’t start to guess. I couldn’t even think how I would describe my new friends and current situation to the typical girl I’d been dating. Intelligent and not particularly innocent as she was, I couldn’t see how she’d be anything but shocked.

Thinking along these lines, I knew I had to call her — at least to tell her where I was, and that I hadn’t forgotten her. Then I fell asleep.

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