Finding My Sir Ch. 02

(You really do have to start by reading "Finding My Sir Ch. 01" to understand this story at all and enjoy it. In the tale, I am 23, and Phil is in his late fifties.)

In the last chapter, dear reader, we met my boss, the famous architect Phillip W, and we saw how he seduced me in a rather civilized, if straightforward way. We also learned how Phillip was seeking a "traditional relationship" with a younger man, like in olden times when men were the authorities over women. In this relationship he would pamper and treasure me, but he would always be in control.

We left off with me standing in Phillip W's penthouse condo, naked in front of his enormous picture window, looking out across the glittering carpet of Los Angeles at night. On my left wrist was the heavy golden bracelet in the form of a chain which he had given me at dinner. Phil had told me to reach back and open my buttocks to show him my anus, and I had done so without hesitation. He had pinched my nipples painfully, and I had accepted the pain. He had kissed my forehead. I had kissed his hand, and I had passed into a kind of submissive trance.

Phillip did not undress at all that first night. He stood in front of my nakedness fully clothed in his handsomely tailored suit and silk tie, but so close that his male scent was in my nostrils, and I could hear his breathing as I held his hand to my cheek after the kiss.

"This is a very natural moment," he said. "You think it unusual, but it is not. The world has always contained Alphas and betas, Sirs and their beautiful boys. Relax as you find this new emotion in yourself, this new understanding of the cosmos, and relax into your role. I'd like to reach down now and hold you by the testicles. Is that all right?"

I released his hand, and nodded.

"Why don't you put your hands behind your head now, Jameson, as I grasp your testicles. You will feel more vulnerable, and you will be offering yourself in a more complete way.

I nodded, and slowly reached up to put my hands behind my head. I opened my legs just a bit more.

Slowly, his hand brushed my cheek, then slid down my neck, my chest, my torso, at last to find my testicles, where he grasped me firmly and possessively. I gasped as an intense erotic surge passed through me and I felt a drop of precum fall from my penis onto his wrist (I say penis, because in our relationship, Phil had a cock, I had a penis.) He nodded in understanding and tightened his grip--almost to the point of pain.

Another powerful, erotic surge passed through me, and I gasped, more from the power of the new emotions I was feeling than from the pain.

I knew deeply in that moment that I wanted this.

His other hand pushed my hair back, stroked my cheek. "You are so very beautiful, Jameson, did you know that?"

"No... no Phil, not really."

"Someone should have told you that you were beautiful, Jameson."

I said nothing, but¬¬¬¬ my eyes locked to his. I kept my hands behind my head. I wanted to keep my hands behind my head. This man is taking possession of me with his hand, I thought to myself, as again the images of a thousand-midnight fantasies passed across my inner vision. Male fantasies. Man-to-man submissive fantasies.

Still holding my balls tightly, he drew my forehead down to rest against his chest, where I felt his warmth beneath his shirt and sport coat. We stood for a time like that, in front of the window, just breathing, together experiencing the change that had come over my world, and perhaps his as well.

"I am going to send you home now, Jameson," he said at last.

"Home?" I said, confused, mumbling into his chest, my hands still behind my head. "I'm....I'm so turned on."

"I have long experience in these matters, my boy," he said, massaging my testicles firmly, still almost but not quite to the point of pain. "You are feeling the first hint of the happiness that comes with recognizing and expressing your true self. You are eager to move forward now, I see that and I appreciate it--but I don't want to take you too far tonight. As it is, once you leave you will feel a shock and a hesitation. Probably the moment you step out onto the street. I would prefer that you get past that shock and hesitation on your own, then on your own come to desire more from me: both my sexual authority and my affection. I have seduced you enough for one night. You must seduce yourself to the next step. Otherwise, this will not go well in the long run."

"I...I don't really understand."

"You are very smart, and you will understand," he said and kissed my forehead, still keeping a firm grip on my balls. "The trouble with seduction is that it's like a drug, and drugs wear off. You must make this important change in your life not just emotionally, but intellectually, and that may take a bit of time."

He paused a moment in thought. "Let's start with a simple assignment, Jameson. It will create some pressure on you, but this will be pressure you must resolve yourself.

"I know you are extremely turned on, but I do not want you to masturbate now, nor do I want you to masturbate when you get home. This will be difficult, I know, and uncomfortable in your balls. I am sorry, but I know it is for the best. You must not just accept my authority, but desire it. You must come to a place on your own where you want to have this relationship with me--and it must be a decision you make when I am not there to influence you."

"I--I--" I stuttered.

His hand massaged my balls and even teased up along my cock a bit as he continued to speak and to hold my face against his chest.

"I want you to go a full day without relieving this sexual tension, my dear boy. During that time you will remember this evening and you will be sorely tempted to cheat, but little by little you will gain an intellectual understanding of the stakes at hand. If you cheat, you will not be accepting my authority except as a game we play together. I want more than a game, and if you keep my command, you will see that it is a true and honest relationship that you desire--and which I will treasure. I promise I will treasure it too, Jameson. If you accept my authority, I will treasure that acceptance deeply."

"When...when do you want me to masturbate, Phil?"

"It's Thursday night now... Go through the day and the next night. Then set your alarm for 7 am Saturday morning, go kneel in the bathroom, and masturbate for me. Text me when you're done. Will you do that for me, Jameson?"

A long moment passed as he awaited my answer. During that time he continued to massage my balls and hold my face to his chest, me leaning forward submissively in front of the window.

"My girlfriend is coming back tomorrow night."

"That could certainly be awkward. Part of this deal is that you would not have sex with her. Indeed, if you agree you will never have sex with her again. You've already explained to me that she's not right for you. No doubt you can have some privacy on Saturday morning to kneel in the bathroom and masturbate for me. Do not send me pictures. I will not send you pictures either. We will never do pictures or anything like that."

"I see."

He pulled my face up then and looked me in the eye. "Do this for me, Jameson, and our relationship will continue to develop. Say no, or lie about it, and we will end it, no hard feelings."

I looked into his eyes. I wanted to do it. I wanted to do it more than anything ever in my life. "Yes, Phil."

"Yes what, Jameson?" he smiled.

"Yes, I'll do as you said."

"And what is that?" he continued. "Come on now, say the whole thing, though saying it may make you cum right here." And with that he just held my balls tightly again.

"I will go home and I will not masturbate. I'll wait until seven on Saturday morning."

Indeed, set an alarm. At exactly seven, get up, stand in your bedroom, and masturbate while holding your testicles tightly with one hand, just as I am holding them now. Think about me as you masturbate. Then text me when you are done. Will you do that for me?"

"Wow." I mumbled, overwhelmed. "I'll try."

"Good boy," he said, "that's good enough for now." And it's true that I relaxed in that moment, feeling that I was free to choose. That I was not giving myself totally to him, so quickly. Thinking that I would have time to think and understand before...well, before...I didn't know what. But he kept his grip as we looked out the window together, letting a little more time pass. "I hate to let you go, but I know it's for the best," he sighed. Then, keeping his left hand on my balls, he took out his phone in his right hand and summoned a car. "They'll be here in 10 minutes, you'd better hurry and get dressed. Oh, and of course, wear the bracelet to bed and when you masturbate."

"I..." I began, but he shushed me.

"Don't try to articulate anything, Jameson. Like I said, you need time to process this intellectually. At 7 a.m. Saturday you will have a choice to make...without me there to enforce it."

And then, before I knew it, I was dressed and downstairs, and a black town car was waiting to whisk me back to the real world. My penis was throbbing, desperate and unfulfilled in my pants. (I say penis because later on, during those happy years, it was understood that Phil had a "cock," while I had a "penis." Even though I was a grown man, and respected as such.)

How strange to turn the key in my loft! How strange to see my girlfriend's dreary canvasses covering the walls! Phil was right: I felt a shock and a hesitation. What the hell had happened? Had I been hypnotized? Had I really stripped and let him touch me...even give me pain? It was two a.m. I struggled out of my clothes and climbed under the covers in only my underwear, let the alcohol have its way, and fell immediately to sleep.

I awoke Friday thinking perhaps it had all been a dream, though I knew it was no dream. I wanted to touch myself as I showered, and I almost did...but then I remembered. I went to work. I did not see Phil at all, as he worked on a different floor now, and I resisted contacting him. He was right. I was having second thoughts. Many second thoughts. What the hell was I doing? What the hell!

Nevertheless, all day at work I could not concentrate as fantasies new and old passed through my head and my penis kept hardening in my pants, even dampening my underwear. I remembered looking at other boys in high school. I remembered looking at muscular men at the beach. I remembered stripping in front of Phil's window. I remembered my desire to call him Sir.

That night, Lori returned from her trip. I greeted her with forced affection, but I told her I thought I might be getting a cold, so we shouldn't sleep together. I would be fine on the couch in the studio/living room of the loft. She gave me an odd look. Something in my manner was certainly off. "You don't look like you have a cold," she said, but shrugged.

At exactly 6:51 a.m. Saturday morning, with no alarm set, I awoke with a strange sense of having forgotten something important. And then I remembered what it was.

I stumbled to the bathroom in only my underwear, peed, and stared into the mirror. Was I crazy? But omg, I still had the golden chain on my wrist...and when I looked at the clock I remembered the actual look on his face when he had told me what to do at 7 a.m. A strange, warm wave passed through my body. Intellectually, I knew I should be ashamed--I mean, I was a fully grown man with a career, a girlfriend, a history, ideas--not someone's "boy." But I did not feel shame. Instead, I felt incredibly turned on. And all at once, I wanted to please Phil...just please him. Just. Please. Him. I felt my penis become firmer in my underwear, and I started to breathe hard. I remembered his hand on my balls. I remembered how I felt when I kissed his hand...how I had wanted to kiss his hand! How I had wanted to complete an orgasm in his presence! To cum for Phil! To cum for my...Sir.

At 6:58, I pulled off my underwear, stood naked before the mirror, put my hand under my balls and squeezed.

"This is crazy," I thought. "Completely crazy." But then I stopped thinking.

He had told me what to do and for a complete certainty I wanted to do it for him. I watched the clock, my penis now fully erect. Right at 7, I began to stroke, standing back to look at myself in the mirror as I held my balls tightly with my left hand and stroked with my right. My eyes closed. Fuck yes. Fuck yes. I dropped to my knees on the cold tile floor. I said aloud, "Yes, Phil, I am masturbating for you." I stroked harder. I gasped. Then I exploded. Truly exploded! My cum covered my hand and made a puddle on the floor.

I felt tremendous satisfaction, and a post-orgasmic clarity I had never known before.

The whole world seemed to fall into place.

I raced back to the studio to find my phone, and with my hand still wet with cum, I texted the famous Phillip W with the words, "I masturbated for you, Phil. Thank you for understanding the need to pause. But I wanted to masturbate for you." He sent back a smiley face, and wrote, "No, thank YOU Jameson. I am overjoyed." At exactly 7:30, as I was making coffee, a knock came at the door, and a man delivered an enormous bouquet of flowers--fantastically expensive with orchids and tropicals, the kind of thing you would see in the lobby of a fine hotel. A gilt-edged note read, "Here's to great beginnings."

I stood there staring at the note a long, long time. Again my intellect tried to reassert itself. And now that I had cum, I was able to consider the situation more analytically. Again and again, however, my intellect circled back to the question, "Does this make you happy?" And incredibly, the answer was yes.

When Lori woke up around nine, she read the card, puzzled. "They like you this much at work? Holy shit."

...to be continued.