A gay story: Finding My Sir Ch. 03 (You really must start by reading both Ch1 and Ch2 to understand this story 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. And you will recall that at the end of the last chapter, I held off masturbating until 7 am Saturday, as instructed by Phil. At 7:30 a grand bouquet of flowers arrived at my apartment, to the astonishment of my girlfriend Lori, who had returned from a trip the night before.)
At 7:45 a.m. that fateful Saturday morning, a text arrived from Phil. His formal tone, including his complete sentences even when texting, always made me smile: “I do hope you like the flowers, dear Jameson. They were sent with great affection. Do you have time for a bit of shopping today? I’d like to buy you some very expensive clothes.”
I looked over at Lori as she made one of her enormous batches of oatmeal, prepared to take her through three meals and a full day of serious painting. Across the room stood a huge unfinished canvas (purchased with money borrowed from me, as I recall), depicting a series of large gray walls broken by only one straggling dandelion. She had been away from her work for nearly a week, and she had a grumpy look as she stirred the oatmeal and studied the canvas.
“Do you think it’s cliché, the dandelion?” she asked me. “I think I hate the dandelion now.”
“Not at all, Lori. It’s not cliché as long as it’s not too heroic of a dandelion.”
“Good point,” she replied. “Still, maybe I should lose it. Gawd, but art is painful!”
As she spoke, I texted back to Phil: “I would love to go shopping with you, dear man.” I put the phrase “dear man” into the text because I could not decide between writing “Phil” and writing “Sir.” This was a compromise, and if I had written “Sir,” as I truly desired, it would have given me an erection. No kidding. But from that moment, “dear man” became my special greeting to him.
“Excellent,” came the immediate reply. “Downtown coffee at Blue Bottle Cafe at 10, then I’ll take you straight to a very special boutique. Dress in your tan slacks, light green polo, and brown loafers. We’ll upgrade soon enough.”
Already I was getting used to the idea that Phil would tell me exactly how to dress every time we were to meet up. I fingered the golden chain bracelet on my left wrist, which Lori had not yet noticed—if she ever would. Already, she seemed like someone I used to know long ago, rather than someone I currently shared a bed with.
“You’re right,” I said. “Lose the dandelion.”
……………..
Promptly at 9:55, my taxi dropped me showered, shaved, and dressed precisely as requested outside a hip little coffee shop downtown. I stood outside nervously. How would we interact? Would we act publicly as lovers? Would it be evident to others that he was, well…you know…
Phil’s BMW pulled up seconds later. He had an actual chauffeur this time, a middle-aged Black man in casual clothing. Phil hopped out of the back seat and placed his hand possessively on my shoulder.
“With Carl at the wheel, we won’t have to worry about parking all day,” he grinned.
“Hello, Carl,” I waved, trying to act nonchalant.
“Hello, Jameson. It’s delightful to meet you,” said Carl, leaning across with a friendly, even warm smile. I saw his eyes go to the golden chain bracelet, and I realized he knew what it meant. Then again came his warm smile.
“Give us about 40 minutes, Carl. I’ll call.”
“You got it, Mr. Phil,” said Carl.
“He knows I hate it when he calls me ‘Mr. Phil.’ It’s like an old movie,” laughed Phil, as the car pulled away. Then he turned to look me in the eye, leaving his hand on my shoulder.
“Happy?” was all he said.
“Yes, I’m happy,” I replied, amazed that our words echoed my very thoughts at 7 a.m.
“I’m so glad, Jameson. Let’s sit and talk a bit before we go shopping.”
“Sure thing, Phil.”
“I will not embrace you in public until you say it is okay, dear boy. But it will be difficult for me to resist. In private, it will be quite different.”
“I appreciate that, Phil.”
“And I appreciate that you wore exactly what I asked, Jameson. Did you enjoy doing that for me?”
“Yes…yes, I did, Phil.”
He smiled a broad smile now. “Perfect! And you look terrific in green. We’ll have to see if we can find you a nice green jacket. Nothing too loud, but still green.”
“Okay,” I laughed.
“That’s it, relax my boy. We’re here to enjoy life together, Jameson. That’s part of the human mission on Earth. To enjoy one another’s company. We must all find ways to do that. This will be ours.”
“I’m sure I’ll relax, Sir.”
“Ah,” he said and smiled, for we both knew how that word “Sir” sounded in the bright sun of a Saturday morning. Another understanding passed between us. We went to sit down.
The coffee came, and we chatted a bit about work and architecture, comfortably as always. A major prize had just been awarded and Phil was full of disdain. “I completely object to this notion that architecture is about creating a piece of art to look at, regardless of how comfortable or practical it may be! Why can’t we have both?” As always, I learned a great deal.
After refills, the subject returned to our impending relationship, and Phil made a bit of a speech.
“I need to make a couple of things clear, Jameson, before we continue—and again, I am thrilled that you have decided to continue. The first is that this is truly an ‘affair.’ I am far too old for you in the long run, and indeed, I may encourage you to have young lovers even now—as long as you are fully honest with me and I have full veto power over your choices. I am, after all, both your ‘Sir’ and your mentor.”
“I…I guess I get that,” I stumbled.
“Like everyone, you should eventually find a mate your own age, male or female, with whom to share life. For a time, I want you and I to deeply enjoy our relationship, and I hope we form a lifetime friendship—so I never want you to feel trapped—or ever think that you wasted any of your youth on me. As you know, I have already vetoed Lori. She sounds loathsome, and as I said Thursday, you shall never sleep with her again. We will discuss new living arrangements for you later this afternoon.”
“Um ok, Phil,” I replied, dazzled by this speech—and by the certainty and confidence with which he said everything. “That’s a lot to process, but I think I’m good with it.”
He smiled. “That was speech number one. Here’s number two: I am a highly sexual being, Jameson. You know that already, and I believe you are highly sexual as well—certainly based on your ready responses Thursday night. Many times I have recalled you naked there in front of my picture window, opening your ass to my gaze and allowing me to hold you by the testicles…so wonderful! Well, I intend to make sure there is an erotic edge to almost everything we share. Let me lay out how that will work.”
He called it the Obedience Game.
“Here’s how the Obedience Game works,” said Phil. “It’s based on surprises. In the middle of a casual conversation, I may suddenly ask you to strip naked. This may be in private or in a secluded but public space. Sometimes in front of others I trust. Another time, I may suddenly ask you to kneel and kiss my hand in public. Or masturbate yourself in a toilet stall at Bloomingdale’s. Or maybe just bend down and tie my shoes as a sign of affection and obedience…just like that.”
“Wow,” was all I could say, but in my pants, my penis had become quite erect.
“Jameson, my sweet boy, you have already demonstrated your intuitive understanding of the Obedience Game. And you are smart enough to see that it is both a game and not a game. Part of the erotic fun and excitement is never quite knowing whether it is a game or not. Certainly, it is always voluntary and never coerced.
“These instructions are intended not to humiliate you, but to continue our erotic engagement as Man and boy. To bring it into every moment. The wonderful part for you is that you need to do no planning for the game—that’s my job. It will be your job simply to obey, without question. You will derive deep erotic pleasure from obeying, as will I from your obedience.”
He smiled as this sunk in. Then he broke off a moment to frame his next words with care. “I will always treasure your obedience, Jameson, as I will always treasure you. Please know that I will not ever intentionally endanger you, and you are free to object for any reason. It may pain me any time you object, and if you cannot adapt to the game, our affair may not work out. But dear, dear boy, I hope it works out.
“Has this discussion made you erect in your pants?”
I stared at him a moment, amazed at myself for not being shocked. For not objecting. My mind went back to that moment when he asked me to strip in his apartment and spread my ass cheeks in front of his big picture window. And then I remembered this very morning when I derived such deep pleasure from masturbating for him at exactly 7 am, as he had requested. I remembered what a revelation it was. It was a…a kind of philosophical relief! Clarity about our places in the universe. I had already made the mental shift, I realized. I had already decided to accept the Obedience Game.
“Well? Are you erect, Jameson?”
I reached down involuntarily to adjust myself.
“Yes.”
“And, do you feel you can play the game?”
“Phil, I…I very much enjoyed the game so far…and thanks for explaining it so thoroughly.”
He looked at me skeptically. “That was rather too easy an agreement, Jameson! I think we need to give the game a try so you see what you are agreeing to. I think it’s time for another little experiment.” He thought for a moment. “Let’s see. Why don’t you untuck your shirt for me right now.”
I laughed. “Um sure, Phil.” I reached down and untucked my shirt from my slacks as I sat at the little table in the crowded café. “That was easy.”
“Now reach down, unzip your fly, and pull your penis and your balls out through your fly to expose them. But carefully arrange your penis and balls so the untucked shirt hides them.” (Careful readers will recall that in our relationship, Phil had a “cock” while as his boy, I had a “penis.”)
“Are you serious? This place is jammed.”
“I’m quite serious, Jameson,” said the famous man. “The Obedience Game, remember, is both a game and not a game. Am I your Sir or am I not?”
“We could get arrested. Or at least I could get arrested.”
“True. You’d better do it very carefully and nonchalantly.” And he sat back to watch.
A moment passed as I looked at him incredulously. Then I casually reached down as if tightening my belt. I unzipped and eased my penis and balls out through my underwear and the fly of my slacks—while I looked to see if anyone was watching. The untucked polo shirt hid my junk, but just barely. Fortunately, the terror had dispelled my erection, but it was incredibly erotic to follow his instructions and to touch myself in so public a place.
“Now put your hands back on the table, Jameson, and relax.”
“Yes, Phil.”
I put my hands back on the table and took a sip of coffee while feeling the strange coolness of the A/C on my nearly-exposed penis. I willed myself not to get the least bit hard and tried to look relaxed.
“Life with you is going to be truly insane, isn’t it?” I said at last.
“I prefer the word ‘adventurous.'”
“How long do you want me to keep it out?”
“Until I say to put it back in, of course.”
“Yes, Phil.”
He got a devilish grin. “The game is already fun, right?”
“Yes, Phil.”
“You are so cute with that nervous look on your face.”
“I’m not cute, Phil.”
“Very well. You are not cute. You are quite manly there with your penis and balls out of your pants.”
“Exactly.”
“But I bet you’re pretty worried about catching those long pubes in the zipper when you try to put your penis and balls back in without standing up.”
We cracked up then, and a few people looked over, and I was terrified enough to take the menu and hold it in my lap, just in case.
“Let’s go shopping,” said Phil at last. “As I promised, we’ll start at Franco’s.”
“Can I put my genitals away?”
“Yes, Jameson, and thank you for asking,” he said quite sincerely. Then he called Carl.
…….
Franco’s Menswear was packed in along a row of a dozen other small men’s clothing stores near Sixth Street in Downtown L.A., and from the outside, it looked much the same as all the others—if slightly higher end. Once inside, it looked pretty standard as well, and the menswear a tad old-fashioned. I was somewhat disappointed.
Then Franco himself came out to greet us. He was perhaps sixty and in extremely good shape with a bald head and little wisp of a mustache. After we entered, he put a “closed” sign in the window and locked the door.
“Phil, it was so wonderful to hear from you! And look at this beautiful young man!”
“I’m trusting you, Franco, to dress Jameson as he should be dressed. And then some. I want to enjoy looking at him every single time I see him.”
“Let’s go upstairs,” smiled Franco.
We headed up a rickety flight of stairs, where the atmosphere changed dramatically. The second floor must have stretched across several of the other storefronts, and I felt like I had entered the drawing room of a fine Victorian mansion. Here were easy chairs and a small bar, low-key fine art, signed photos from sports celebrities, a small putting practice carpet, a slight scent of cologne, and a general sense of masculine serenity. And yes, highly-curated racks of expensive-looking, up-to-the-minute, big-name men’s clothing. At the far end of the room, I also spotted a few racks of what looked at first glance like black leather harnesses for horses.
Phil poured himself a scotch, seated himself in a large wing-backed chair, and made ready to enjoy himself. I was led to a small circular platform in the middle of the room, lit like a stage.
“Please, Jameson,” said Franco rather gently. “Remove your clothing so I can take your measurements.”
I looked over at Phil.
“Everything, dear boy. You won’t need any of that clothing when we are done. Don’t be shy. Franco is an old friend.”
“Yes, Phil,” I said.
“He’s a good boy, isn’t he,” said Franco in appreciation.
“Yes, he’s a very good boy,” replied Phil.
Then they both went quiet to watch.
I sat down on the platform to remove my shoes and socks, and then I stood up and I proceeded to strip naked, handing each piece to Franco. I did not even hesitate when it came to my briefs, as I knew that Phil had said “everything” and I did not want him to have to say it twice—the Obedience Game already doing its work on my imagination. Phil continued to say nothing: just sat quietly sipping his scotch and enjoying the show. For all the time we were together, he loved to see me undress—and never tired of it. Always Phil treated my undressing as a kind of sacred act: and never wanted any talking or interruption while it proceeded.
When I finally stood up stark naked, I had a slight erection. How could I not? Of course, Phil was still fully dressed. And for that matter, so was Franco. It was just me naked: “the boy” on display, wearing only the gold chain bracelet. Being naked in front of these clothed men was astoundingly erotic.
“Lovely, don’t you think, Franco?” asked Phil.
“Absolutely gorgeous. Jameson, it will be a real pleasure to dress you. Are you going to shave him, Phil?”
“I think so, yes. I will likely leave just a little landing strip, as is the current fashion for boys. Perhaps this week.”
“It makes a little difference in fabric choices, that’s all.”
“Jameson, you understand where I’m going with this? Will you agree to be shaved for me?”
“Yes, Phil.”
“Good boy.”
“Why don’t you touch yourself just a bit, thinking about being shaved for me.”
“Yes, Phil.” And incredibly, as if in a trance, I reached down and stroked my 7-inch cut penis just a bit as the men watched. I, a fully-grown 23-year-old with a degree and a job and a girlfriend and a future. I had just consented to be shaved! it didn’t seem real, but I also did not object, even in my mind. It all seemed so natural as I stood there naked on the little platform for my new Sir.
Franco then proceeded to measure me. He was completely unselfconscious about the act, and it was intense as he wrapped the tape around my naked torso and naked chest, measured my neck, measured around the furthest extent of my butt cheeks, up around under my butt cheeks, then made me stretch out my arms for measurement, and open my legs to measure my crotch-to-floor length. He even slipped the tape around my genital root under my balls to measure for…who knew what.
My erection increased, but neither man commented about it, Franco was careful never to touch it, and Phil clearly enjoyed every moment of looking at it.
Finally, Franco rolled up a portable rack and began bringing out clothes. There were designer jeans and designer sportscoats, designer shirts and designer shoes and designer socks. He brought me some tight briefs to restrain my erection, “Let’s try these,” was all he said… but I got control of it myself. For perhaps two hours I stood on the little platform in the bright lights as I tried everything on and Franco fussed. Prices were never mentioned. Phil had to approve every decision, of course, and I was sad to miss out on some pieces I liked. Once I begged him to include a nice black shirt with subtle white ticking, but he refused. “You just don’t look good in black, Jameson, you are too fair. That’s a no.”
Lunch was brought in at some point, and we took a break to eat. Phil asked me to remain in my briefs as we ate, and of course, I complied. Both men seemed to enjoy eating with a nearly-naked “boy.”
By the time 2 pm rolled around, I had a completely new wardrobe—well, almost.
“Just fabulous, Franco. Now let’s get to the erotic wear.”
“The erotic wear?” I asked, standing in just a pair of Italian briefs on the little platform.
“Yes, Jameson,” said Phil. “Franco stocks the very best.”
My eyes went wide as Franco wheeled out a portable shelving unit with stacks of men’s briefs.
“Start with the G-strings,” said Phil. I blushed, then I obediently stripped off my underwear and took the tiny white G-string that Franco handed me. It was difficult to untangle and put on, especially while being watched by the two men. At last, I had it on…it ran up my butt and tightly pouched my genitals. Fortunately, I was past having erections at that point. Then came an Andrew Christian garter with mesh—which Phil rejected as insufficiently masculine. This was followed by an Andrew Christian jock thong and a thong with a detachable crotch cup. One pair of undies had a carefully-tailored, form-fitting pouch for a man’s penis and articulated balls. It would expand with an erection, said Franco, and stretched it out to demonstrate before I pulled it on. Phil insisted on that one. Several pieces featured “easy access from the rear.” One even had a zipper along the butt crack.
“We want to have plenty of options, dear boy,” said Phil when I showed some impatience. “I mean, on some nights we could do a whole fashion parade, right? Or think how fun it would be if I had you wear some of these to work, under your clothing. You could text me pictures from the men’s room!”
“Yes, Phil,” I said obediently. And as I said it, lo, my erection returned.
Franco noticed and gave me a nice smile. “Are we going to look at leathers today, Phil? I have a new rig in from France you’d really like.”
“No not today, Franco,” said Phil.
“Leathers?” I asked, and my eye went to the far end of the room where I thought I’d seen the horse harnesses. Now I understood. I’d seen pictures of such things.
“Another time, Jameson. We’re not at that stage, you and I. I will decide when we are ready.”
“You will decide, Phil.” I was standing in a kind of jockstrap made of silk which did exactly nothing to hide my genitals, and there was another pause as my eyes met his in the Obedience Game. My erection instantly surged. Franco knew better than to say a word…that’s why he could charge the prices he charged.
Phil, of course, chose what I should wear out of the shop—white slacks with a no-lapel heather green sportcoat made in Italy, along with some soft leather sandals. Under the pants, I wore the white silken jockstrap….just because.
We carried a few bags with us, but Franco would have most of it delivered, along with the many pieces that needed alteration. “We may have to have him back to ensure a good fit over the butt,” warned Franco. “Jameson has a wonderful butt, but it has a very special shape.”
“Delivered where?” I asked, back in the car.
“My place for now,” said Phil. “Until we can find you a new apartment.”
I glanced up at the front seat where I knew Carl could hear every word we said.
“I have no secrets from Carl, Jameson. None. You can always speak freely in front of him.”
“Just pretend I’m not here,” chimed in Carl. “Someday it will all go in my novel, with the names changed of course.”
“Holy fuck,” I said.
“Fucking is indeed holy, in my opinion,” said Phil. “Please be more careful with language, and do not use that word unless we are in the holy space of the bedroom.”
“Okay, Phil,” I said. “I’ll be more careful with my language.”
“Thank you so much, Jameson. I know it’s hard to change the crude habits we have all learned in this time.”
I paused, then continued: “I can’t afford a new apartment, Phil. Not right now.”
“I can afford it, Jameson. And as I said on our date, I will also be providing you with a generous allowance. I can’t have you living a substandard life while under my mentorship.”
“I can’t let you….”
He looked over and raised his eyebrows in expectation.
“Yes, Phil,” I said and nodded.
“Superb, Jameson. What a wonderful day so far!”
For the first time that day, his hand strayed to my crotch, where he gave it a little squeeze of affection.
“On to the shoe store—you know the one, Carl. And then, I think Giovanni’s Haberdashery. I didn’t want to say, but I thought Franco’s shoe selection was abysmal today, and I hated all the ties.”
“But we bought these sandals, and I think three ties.”
“I didn’t want to insult the man!”
His hand stayed on my crotch, tightly, and I put my hand down on top of it with affection as my erection increased and he squeezed harder. I was getting used to the idea that when I was with Phil, I would be touched casually, and my erections would come and go more or less constantly, as he desired. I wondered about his erections…but I could not tell by looking. Already I wasn’t worried about Carl seeing this kind of play.
“Thank you, Phil, for all the fine clothes. They are amazing.”
“We will enjoy them together, dear boy. I am a religious man. As I said, I believe that we were put here to enjoy each other’s company, but also to take care of one another, to create and enjoy beautiful things together, and to maintain the dignity of human culture…together. Think of it as art and humanism merged, in architecture and in life.”
His grip became even tighter and I could not help but squirm just a little. Then he unzipped my fly and reached in and caressed my penis, barely covered by the silk fabric. I glanced at the front seat, where Carl kept his eyes steadfastly on the road. I allowed myself to enjoy Phil’s touch. To become very hard for him. To relax.
In a few minutes, we pulled up to a store where the sign read, “Fine Italian Footwear — Exclusive Importers.”
“Can you hold on just a moment, Carl? Jameson will need to reduce his erection before we leave the car. These new pants are so tight, people will see everything.”
“No problem, Mr. Phil,” said Carl. “I can pull up right here, and I’ll turn up the A/C.” Which he did.
“I could use some new shoes myself,” said Phil idly as he removed his hand and zipped me up. I was still gripping the seat and breathing hard.
……………..
Night came.
I had been anticipating night with a mixture of excitement and fear, for I knew with certainty that I would have sex with Phil, and I was nervous about it. He did not touch me again during the drive to his building, as we passed through the streets, I realized that I had never even seen Phil with his shirt off, much less seen his privates, though he had seen me naked — and “more than naked” when wearing a silken jockstrap. And of course, he had handled me now several times in the way a strong man handles a lover. What would it be like to make love in such circumstances? It was all very well to be submissive, to be treasured, to be handled, to have my erections stimulated by this man as in my many fantasies—but all very narcissistic and safe in its way. Now, to have sex with a man? I had often imagined the specifics of sex with a man–and always with a stronger, dominant, older man. But in real life? Would I…actually like it? I fingered the golden chain around my wrist.
When we got to Phil’s magnificent condo with the broad view of Los Angeles, the sun was long past setting, but its afterglow could be seen through the enormous, gold-framed picture window that faced west. Carl helped carry up bags and boxes.
“Please call Lori and let her know you won’t be home tonight,” said Phil. “You needn’t break up with her on the phone. Make some excuse. You will break up with her on Monday.”
“Yes, Phil.”
As I made my call, Carl unpacked bags and laid out clothing for me on the bed in the spare room. A selection of “erotic wear” mostly, but a few practical things for the morning as well. He never said a word and was careful not to catch my eye in case he might embarrass me.
Dinner arrived, delivered from a very nice health food place nearby.
And then Carl was gone. Now it was just me and my new Sir.
We stood together looking at the last of the light to the west.
“Jameson, I’d like you to wear those white shorts for dinner, along with the green Italian coat, but with no shirt. Wear the genital-form-fitting briefs underneath—you know the ones. Why don’t you take a shower and change while I lay out this wonderful food? I will shower later.”
I turned to meet his eyes. He reached out and stroked my cheek as he had on Thursday, and I felt again the happiness I had felt after my obedient masturbation in the morning—that sense of rightness coming into the universe. I turned my head slightly and kissed his palm as it passed my lips, and I said,
“Yes, Phil.”
…to be continued