Finding My Sir Ch. 04

(Dear friends: You really must start by reading all three of the previous chapters to understand this story at all, and enjoy it. Trust me, it's worth the effort. As a reminder, in the tale I am 23, and Phil is in his late fifties. Phil has a passing resemblance to Gregory Peck at that age...you can search it. We are in Phil's penthouse at the end of our day of shopping.)

*

"Go on then, Jameson, take that shower," said Phil with a smile. "It's just us now." He switched on some light jazz and began opening up the packages from the restaurant. I watched his back for a moment, draped as always in a well-tailored suit. I tried to imagine him naked, and I could not.

Then finally I turned away and walked to the guest room—a cozy little bedroom and bath filled with shelves of mementos from Phil's travels around the world: statues and masks from Africa, a paddle hung on the wall from the south seas, a kachina doll, a signed soccer ball, and much more. A smallish window looked to the east, to the skyscrapers close by and searchlights around the stadium.

On the twin-sized bed were the clothes laid out for me by Carl, and in the center were precisely the items Phil had just asked me to wear: the darker of the two green no-lapels Italian jackets (more appropriate for evening), very small white shorts, and those white, form-fitting briefs with the tight, expandable sock for a man's genitals. Apparently, Phil and Carl had discussed my wardrobe for the night.

On the side table was a note: "Dear boy, you should have asked. Given your uninteresting history, I am not worried about you." Stapled to the note was a medical report on Phil from five days earlier, showing negative on several terrifying tests.

I laughed at the note and at my own naivete in such things.

Then I stared at the clothing, and I was momentarily filled with doubt, much worse than on the drive over; for now, I was at least momentarily alone, away from the powerful presence of Phil. I stripped down to the silken jockstrap and I went and looked at Downtown L.A. again, then at myself in the mirror, remembering with amazement my submissive behavior all day long: how I had played the Obedience Game and how it had aroused me at every point. How I'd been on display at the menswear store. Did I look the part of a "boy" at 23? Perhaps. Had I enjoyed that feeling of obedient arousal all day long, including when Phil stroked me through my pants in the car?

The answer was yes. Yes, I enjoyed it. Indeed, thinking about it began to arouse me even now. But was I right to enjoy it, or was there something fundamentally wrong with such enjoyment? The Game seemed so...so fundamental to my nature. It fulfilled so deep and lifelong a desire, going back to my earliest sexual fantasies. Even my sometime attraction to Lori, I realized, had something to do with her evident control over me. "You are all in now, Jameson," I said aloud, pulling off the silken jockstrap

In the shower, I washed myself ever so carefully, thinking about how Phil said so casually to the owner of the menswear shop that he would have me shaved. When he had said that it had given me an erotic surge...partly from the tone of possession in his voice, partly from the intimacy of the statement to a stranger. Now, standing naked in the shower, I stroked my fingers through my pubic hair and through my underarm hair, and actually tasted the water, tasted my maleness in the water. "A little landing strip of pubic hair" he had said. Fuck. What would that be like? Not just my clothing, but my body hair controlled by Phil, sculpted as he desired. Phil choosing my food when we went to dinner. Phil choosing where I would live, and who would be my lovers. But as I thought these thoughts and looked for any sign of rebellion in my soul, my penis grew to an erection, and in my imagination I saw Phil mounting me from behind, entering my ass. Indeed, my penis stayed erect as I toweled off carefully and pulled on the form-fitting white brief with the clinging cock and balls sock that he had requested. I pulled the tight white shorts over my erection with some difficulty, then slipped on the beautiful Italian jacket without a shirt, admiring my flat belly and defined abs as I knew that Phil would admire them.

I wanted to please him. I really did.

"Jameson," I said aloud as I replaced the golden chain bracelet Phil had given me, "What is the point of thinking after today? You have given up thought in this matter. At 7 a.m. this morning, when you masturbated at Phil's command, you stepped past thinking, and you have enjoyed being an obedient boy all day. Don't think anymore."

We would have dinner and then we would have sex. I would have sex with a man for the first time in my life, but mostly I would be having sex with Phil—a man at least twice my age (and maybe more, I didn't dare ask). Or perhaps I should say that Phil would be having sex with me. My Sir will be having sex with his boy. That is what I wanted, and that is what I had just a small taste of Thursday night when he had held my testicles in front of his picture window, and I had parted my ass cheeks to show him my anus.

"It is decided," I said aloud. Carl had left a pair of white leather sandals at the foot of the bed. I slipped these on and exited the bedroom.

Dinner was laid out on a small white lacquer table by the huge picture window looking west from our great height, across the multi-colored sparkle of the megacity, out toward the darkness of the sea. All sunlight was gone now, and this being L.A., only a few stars shown; but I could see a surprising number of lights in the sky from airplanes and helicopters, moving slowly like fireflies across the bright landscape.

Phil stood smiling, holding out my chair for me. He was still in his dark gray suit. Indeed, he had re-tightened his tie.

"You look beautiful, Jameson. Thank you so much for today. I will never forget how fun it was to dress you properly."

"Thank you, Phil, for the clothes. And it was an incredible day. I hate to think what you spent."

"I am especially honored by your erection right now, dear boy. Really, I had not expected it in anticipation of the evening. I believe you are erect because you are wearing the clothes I asked for and you are still feeling the Obedience Game."

"You're probably right, Phil," I said, without embarrassment. After all, all day I had been on display, with and without erections as I had tried on clothes for Phil and the shopkeepers. Carl the chauffeur had even seen me erect in the back seat of the BMW. Embarrassment, it seemed, was a thing of the past. Embarrassment was now something other people wrestled with, people who had not agreed to an Obediences Game. I had always been easily stimulated, since the first stirrings of my puberty. Embarrassment had dogged those days. No more.

"Jameson," he said with a smile and a voice of playful command, "Stand up, unzip your fly, and let the sock with your penis and testicles out while we dine. I don't want them uncomfortably trapped in those shorts. You won't enjoy your dinner." (Readers will recall that in our relationship, Sir had a cock while I had a penis.)

"Yes, Phil," I said with a little laugh. I stood up and unzipped the fly on the very tight white shorts and pulled out my genitals, fully defined in the sock. Then I sat back down.

"Great game, you have to admit, my boy."

"As you said, it keeps an erotic edge to just about everything."

"You will love this wine," he said, as he poured for me and for himself, then sat. We were angled so we could both look out at the view...and so that Phil could reach over and touch me with his left hand if he wished.

"Now tell me your thoughts about male sex," he said.

"Male sex?"

"Yes, male-to-male sex."

"I...I've never tried it."

"I know that, dear boy. But you've thought about it."

"Well...yes. I've imagined it...many times."

"And you've looked at gay pornography."

"Sometimes...yes...yes, I have."

"I'm sure you know the mechanics, but what do you think of the psychology of man-to-man sex?"

"The psychology of it?"

"Yes. You know, back in the dark ages of psychology in the late 19th and early 20th century, some foolish doctors surmised that men who desired men were narcissists who actually wanted to have sex with themselves. Others thought it was a kind of confusion by mama's boys without male role models. They called it 'inversion.' But they were all idiots, and they missed the obvious."

"What's the obvious?"

"Well, for starters, men fall in love with men and want to be close to them, just like men fall in love with women and want to be close. And of course, some men do harbor female personalities...not you, of course. But I'm interested in something rather different, and perhaps more primitive yet."

He paused.

"You see, dear boy, in all sexual relations, there's an element of power exchange, of claiming. Most often the man claiming the woman as his exclusive mate. In my humble experience, this is often even more true in gay sex, where I personally believe that power exchange and sexual claiming express, well, the primal order of the pack. On Thursday night I alluded to Alphas and betas, Sirs and their boys. Let me expand on that now."

"Um, okay, Phil," I said, no longer surprised when my new Sir began a speech.

"As men, we are pack animals in quite a different way than women. We are not unlike the wolves, where there's one male Alpha and a pack full of male betas whom he dominates. Look at the men in any business office. Any army. The troops are not any less masculine than the leader, but they often express that masculinity in pack obedience. In the gay world, at least in my humble experience, there are many more betas than Alphas. The Alphas want to express their dominance, but the betas truly want that dominance, because they have a deep need to follow the Alpha. They find within themselves a primitive, inescapable need to express their submission. It's just the natural order of the universe, very sexy, and nothing to be ashamed of for either party."

"This is as wild as your speech on our first date, Phil."

"I suppose so. But I'm telling this to you to prepare you for our first time having sex tonight."

"I'm ready, Phil," I said, in quite a serious voice.

"I know that, dear boy," he smiled again, and without hesitation, he reached over and stroked my penis through the underwear sock a couple of times. I leaned back and again allowed him to touch me as he wished. I wanted to be touched like that, casually, all the time—whenever he wished. He lifted his hand to his nose afterward and inhaled a moment, then went on:

"But I also realize that I am more than twice your age, and you are very likely nervous that you will not enjoy having sex with a man of fifty-eight. I am in good shape, but I am no Adonis. I also realize that after my speech on Thursday night and my discussion of shaving you today, you may be worried that I am thinking of you in some feminine way.

"That is both true and not true. I do not at all think of you as 'femme.' I know you are a very manly dude, and I love that. Nevertheless, you are to me a boy who will someday come into your own full manhood, but not quite yet. It is a wonderful moment for us both to enjoy. Perhaps you will choose to be a Sir yourself. Or perhaps not. Perhaps you will marry a woman. In any case, you are presently a beta, and you know yourself to be a beta, and it is your natural duty to serve an Alpha and Mentor. This is what I want you to have in your head when we have sex—you will find this truth quite as erotic as any attraction to my body."

I began to protest, but he cut me off with a wave.

"I will be claiming you, Jameson. I will be taking your anal virginity in a similar way to the way a man takes a woman's virginity. I am yang and you are yin, and in that manner, we are an expression of masculine and feminine, regardless of how manly you are. It will be rough. A claiming is often rough. But I want you to love it. I am deeply attracted to your beauty, but it will not matter so much if you find me beautiful, because if you concentrate on being claimed, in this way of giving yourself to your Alpha, you will let go and truly love it, I know. You will be happy submitting, as a woman is happy that her beauty has attracted a strong man. All quite natural."

I stared at him, mouth open, for quite a long pause.

"You may now say it, dear boy."

"Say what?"

"That word you've been wanting to say all day."

"What word?"

"Sir, of course. You may now say, 'Yes, Sir, I understand, Sir."

Our eyes met.

"Yes, Sir, I understand, Sir."

"Say it again."

"Yes, Sir, I understand, Sir."

He reached down and again took hold of my erect penis, sheathed in the thin material.

"Now say, 'I wish to be claimed, Sir.'"

I swallowed hard. "I wish to be claimed, Sir."

"Kiss the bracelet I gave you, Jameson."

Looking deeply into his dark eyes, I raised my wrist to my lips and kissed the golden chain.

He smiled and relaxed his grip. "I've been going on and on and the food is getting cold. Should I pop it in the microwave?"

"No, it's probably fine like this," I said, a bit rattled.

"I agree. I take out from this place all the time...try the beet salad first. No, first try that wine! It's a Vouvray from the center of France. A bit sweet, but it goes with the cheese."

I took a deep sip of wine, and the meal proceeded delightfully, our conversation as always running smoothly with no further discussion of sex, even though my genitals were out the whole time in the sock (though, thank heavens, now flaccid). The wine got us talking about all things French. I told Phil about my French cousins in Canada. He told me about negotiating with the French over the design of a museum. We had lots of Vouvray.

----

At last, my Sir leaned back and held up his empty glass.

"It is time, dear boy."

"Yes, yes of course," I said, suddenly remembering what came next. Had I really forgotten? I remembered suddenly the words that had slipped right by during his long speech: It will be rough.

"I am going to go and take my shower now. Perhaps you would be so kind as to clear up. Then I'd like you to wait for me in front of the picture window—it was so wonderful on Thursday when you did that. Strip down to just these amazing briefs and stand there waiting with your hands behind your head and your legs slightly spread."

I took a deep breath. "Yes, Phil," I heard myself saying.

"Thank you, Jameson." He brushed his hand along my cheek, and I thought for a moment that he might kiss me, but he did not. Indeed, I realized that we had never kissed on the lips at all. He had kissed my forehead and neck. I had kissed his hands. But the intimate kiss of lovers had not been shared. Was a kiss on the lips a part of the claiming? Or would we never be that kind of lovers?

And then he was gone to his room.

I quickly cleared the table and then pushed the table itself out of the way so that the full glory of the huge picture window would not be obstructed. For the first time, I noticed a large white pad, rather like a mattress, in an oval shape just to the right of the window, and I wondered at its purpose.

Then I removed the jacket, shorts, and sandals until I was naked except for the tight white briefs with the stretchable sock to hold my genitals and the golden bracelet. I went and stood in front of the window as instructed, looking out, placing my hands behind my head, parting my legs, and breathing hard. It was the same stance I had taken at the end of Thursday night, this time with my back to the room, and again I found it deeply erotic. It was the stance of a soldier at attention or the stance of a willing slave. It was strangely masculine though fully submissive. With my hands behind my head, I was extra aware of my golden chain on display. I listened to the slight sounds of Phil preparing in his room, and of the water running as I waited. My erection returned, as I knew it would, as I knew it always would for my Sir. His words about betas and Alphas, yin and yang, feminine and masculine ran through my head. He was right, it was my need for submission to his dominance that drove my libido in that moment, not the anticipation of his naked body.

When I heard him enter the room, I did not turn. Instead, my body stiffened to be even more like a soldier, presenting myself. He spoke not a word but walked up behind me and ran his hand over my buttocks, then over my shoulders. Then he walked in front of me. I did not look at him, but kept my eyes forward. He touched my breasts, my nipples, ran his hand along my abs and my obedient arms. I saw that he was wearing just a dark robe of Asian design. He held up a pair of scissors and smiled. Then he pulled at the material of my briefs and began cutting it away. At first cutting carefully around my genitals so the sock was cut off and my erect, circumcised penis and balls stood forth naked, framed by my reddish pubic hair. I did not move as he did this, and I did not move as he then stroked my naked member for a time without speaking. I simply stood at attention, hands behind my head. Then he walked around behind me again. He pulled at the material on my rear and cut out a circle above my anus. There was no hurry, and I could not tell if he had pre-planned these precise actions, or was just doing what pleased him in that moment. He could do what he wanted: we had agreed on that.

My Sir then walked back around front and produced two objects from the pockets of his robe. The first was a small bottle of lube, and the second was a black silicon anal plug in the shape of a 3D ace of spades, with a black glass jewel embedded on the foot of the plug. I had seen such things on certain websites. I had thought more than once about purchasing such a thing and trying it in my ass. I had never seen one in real life.

"This will begin to stretch you for your claiming, Jameson. It will hurt when I insert it, but if you relax, it will stop hurting, I assure you."

I nodded slightly and braced myself. The word claiming, of course, echoed loudly in my head.

He lubricated the anal plug as I watched, then walked around behind me again and began to insert it through the hole he'd cut in the briefs, above my anus. I took a sharp breath. As the plug stretched my sphincter it hurt a great deal. Then it popped in and hurt a bit less. And within thirty or forty seconds, it hurt not at all. Instead, I began to feel an exquisite, if embarrassing sense of being filled and stretched, along with a yet deeper submission. I thought about the black glass jewel being visible from my behind, masculine and feminine at the same time. It was the first toy I had ever had in my ass, and it was the second symbol of my Sir's ownership, after my bracelet. I stood up straighter, but my Sir said:

"Kneel, Jameson."

The words should not have shocked me, but they did. I knew what it meant to kneel in this moment. The sexual event which the kneeling would make possible.

I knelt, keeping my hands behind my head, but now lowering my eyes in submission.

My Sir came and stood in front of me, very close. I heard more than saw him remove his robe to reveal his nakedness. I stared at his feet, scared to look up. His legs were strong, hairy: black hair with some gray. I could smell his crotch, fresh from the shower. He said nothing. I did not dare to look up at his crotch—so that, before I ever saw it, I felt his erect cock touch my face. He was holding his cock, rubbing it on my face, leaving little trails of wetness that I realized was precum. I was aware that he was also circumcised, something I had wondered about idly all afternoon. I raised my eyes slightly to his strong, hairy thighs, his thatch of pubic hair, his testicles hanging low with middle age. And at last, I saw his large, powerful cock, thick and veiny, held in his fist, moving over my face, painting the little trails. My first time seeing his cock was like that, not just in my face but on my face, marking me.