Jimmy, Round One
Three weeks after my blind date with the delightfully submissive Chris, the teasing waiter from the bar where our blind date had started came back into my life. We were hiring an office assistant, a general gofer, in the office, and there he was among the applicants. His application wasn’t among the best, and I certainly didn’t know him from Adam before the interviews, but somehow he had managed an interview appointment with me.
I recognized him instantly when he walked into the office, and it was clear that he knew exactly who I was and where he’d last seen me as well.
The interview was a little awkward, and I asked him some pretty tough questions, trying to make him see that he just wasn’t qualified for this job.
“You don’t even look like you’re old enough,” I said.
“I’m nearly nineteen,” he said. “You can see it right there on my application. I’ve graduated from high school and am taking a weekend college course--and I’ve worked for a living for nearly five years. There probably isn’t anything in this job that I haven’t done for a boss already.” He gave me a meaningful look, which I chose to ignore.
“I just don’t see the qualifications in your application,” I persisted.
“I’m sure I’m qualified, probably the best qualified,” he said, batting long golden-red lashes, covering enticing green eyes.
“How do you figure that?” I asked somewhat belligerently.
“I’ve been a cocktail waiter for some time now. That made me the gofer for the bar, and that’s essentially what the job you have here is. A gofer. I am interested in being a full-service employee here. I know you’ll be pleased with my service.”
“I don’t think you have any idea what you are suggesting,” I said. I stood up, flipped my tie over my shoulder, unbuttoned the three middle buttons of my shirt, and pulled it open, revealing the rough leather strapping criss-crossing my chest.
“Oh, I think I do,” he answered, as he stood and walked over and fingered the metal ring on my sternum where the straps met. “I’ve talked with Chris about you. He’s one of our regulars at the bar.”
Of course he was the one who got the job.
Three days after Jimmy started, he stayed late to help me wrap up a sticky project proposal. I was tense and tired and grouchy, and he was being just as helpful and understanding as he could be.
Long after all of the lights in the other offices had gone off, I reached a difficult point in what I was writing and couldn’t decide just which way to take the proposal from here. With an “Arghh,” I just threw myself back in my chair and laid the back of my hand across my eyes.
“What you need is to release some of that tension,” a voice wafted over to me from across the room.
I opened my eyes, and there Jimmy stood, in the doorway. Completely naked. His compact little body was beautiful. He was on the solid, curvy side. A barrel chest, tapering down to a thin waist and hips, but with round, bulbous butt cheeks. He was a natural redhead, and a respectable cock and set of balls plunged down from a profusion of pubic hair. There was a curve of curly red hair cupping both of his bulging pecs and a trail of hair traveled down his chest and belly and met his pubes. His thighs were covered in a red down. He’d let his hair down, and it fell down to his shoulder in a curly profusion. He looked like a Greek warrior to me. Compact and proficient, and covered in brown freckles.
But what really, really aroused me was that he was fisting and swishing several leather straps at his side. His clothes had been piled up beside him just inside the door, and when he was sure he had my attention, he had leaned down and picked his jeans up from the floor and pulled several lengths of leather straps that he’d been using as a belt out of his belt loops.
I sat there, wary, as he dropped the leather straps, strutted over to me, and reached down and unbuttoned my dress shirt. He knelt in front of me, between my spread legs, and kissed and tongued his way around my nipples as he unbuckled my belt, unbuttoned my trousers, and unzipped my fly.
I heard the intake of his breath, when he found that, instead of briefs, I had a leather strap coming down from the metal ring at my sternum and connecting to a leather sac pouch and a leather cock ring with metal studs around the base of my tool. He fished out my cock and made all of the usual appreciative comments I’d heard from my previous lovers about its length and breadth. He sucked me off, and I just sat there and let him do it, letting him slurp on my engorging dick as he ran his hands around my chest, wedging his fingers between the tight leather straps and my skin.
I was still sitting there, in passive shock, as he stood up, reached behind him for a tube of lubricant, greased up my pole and then came down with his knees on either side of my thighs and slowly, and with a lot of noise and thrashing about, lowered his ass on my erect cock. Not much more than the dick head had disappeared, though. He was having trouble taking me in. He was pretty tight even when he was stretching as much as he could.
I was feeling nothing, though, and the tension was building rather than receding. This isn’t the way I wanted it. This wasn’t what turned me on. He pulled my head up to his with a grip on my tie and kissed me. This wasn’t me controlling the fuck. This was him, a young tease, controlling me. I wasn’t the boss; he was trying to be the boss.
With a feral sound emitting from my gut, I rose up out the chair and turned him and slammed him down on his belly on my desktop. Ripping my belt out of my trousers, which had fallen to my knees when I’d stood up, I tied his hands together above his head. Leaving him there for a couple of seconds, winded from an unsuccessful effort to fight me on tying up his hands, I went over to the door and found the leather straps he’d been swishing around earlier and had dropped there and, returning to the desk, wrapped and tied them around Jimmy’s legs just below his knees.
Then I showed him that, with me in control rather than him, I could get my big cock into his ass even when his passage was tighter than it was when he tried. I grabbed his bulbous butt cheeks with my hands, positioned my cock at his hole, and pushed, ignoring my own pain at the tight fit. Of course he yowled in pain and frustration, as I pushed in three inches in one strong, initial thrust.
“Ahhh,” he yelped. But then he wiggled his butt at me.
“Any more?” I asked. “Have you had enough?”
“Piece of cake, boss man,” he yelled back at me. And then he laughed.
He laughed! Five inches into him, with both of us grunting from the effort and pain. But he was still laughing.
“What is it with you?” I said. “You said you’d talked to Chris, and he must have told you what I liked.” Six inches in.
“He did,” the young man replied and then laughed again. “He said you were into total control. Well, I’m into controlling the controllers. You can’t touch me. I don’t care how long or thick you are. Before you’re done, I will have tamed you. Admit it. You love my body and this ass.”
And I did. I loved fucking this red-headed warrior. But control was necessary. No, control was everything. With a thrust, I went in to the hilt. All eight and a half inches.
He was gulping and panting and grunting now. But he also managed a weak laugh. “Untie me, man,” he whispered. “Untie me and let’s fuck on equal terms. I can make it so nice for you.”
He simply didn’t understand. I had to have control and tightness and total submission. The pleasure just didn’t reach where it needed to go without that. He was wriggling his butt at me again, stroking against my buried cock, so that he was fucking himself. This wasn’t the control I needed.
I turned, searching the office. The window blind cord. I pulled out of him, and went over and jerked it down. Then I went around to the front of the desk and tied one end through the belt holding his hands together over his head. I ran the cord back through the kneehole in the desk and tied it through his leg bindings and pulled the cord tight, holding his legs and arms still with the tight tension of the stretched cord. When I was in the front of the desk, I’d notice that there was an open slat there at the top of the kneehole. I ripped off my tie, and made a noose knot in it and put it over Jimmy’s head and tightened it around his neck. I tied the other end off through the slat, thus keeping Jimmy’s cheek flat against the desk top. He was totally trussed up now. I had physical control. Total control. What could I do about total submission. My rocks ached. I needed to get them off. I needed to release this tension.
Maybe eight and a half thick inches weren’t enough with this guy, even with his ass tightened up. I reached down and opened the bottom drawer of my desk and buried my hand under a pile of papers. I came up with a two-inch extension capped with an extra large stud-covered bulb I’d bought but never used before.
I sheathed my cock with the oversized studded harness and positioned myself behind the fully trussed figure again. Once more, I palmed the rounded butt cheeks and pushed my sheathed cock up to the opening of the puckered, lubricant-slathered hole with its circle of golden-red curly hair. Jimmy moaned and groaned “Oh, shit. Oh, God, no, nooooo!” he muttered, as I rotated the studded sheath head around his hole, relentlessly working it into the hole.
“The only way you are going to continue working here and having the privilege of releasing my tension is by submitting totally to me,” I said. “Do you submit?”
With a push, I’d worked the sheath head and the extra two inches into the asshole.
Jimmy cried. “Yes, OK, I submit!”
“That sounds good, but I don’t believe for a minute that you believe it yet.”
Now the first of my own eight and a half inches was inside. Then I was up to the rim of my own dick head. He was trembling under me and moaning for me to stop, that I was splitting him. Several more inches in and he was beginning to really feel those studs. I took the unburied part of my dick in my hand and rotated it around in his canal, coaxing him to open more to me. He was crying and moaning now. The laughter was behind us.
He kept screaming that he submitted, that I’d won, and I kept creeping up his canal, until I only had three inches outside him. With the extension, I was in a good seven and a half inches now.
“How? How can I convince you I submit?” he whimpered.
“I’ll feel it in your body,” I answered. “When you’ve totally submitted, all of the tension will go out of your body, and you’ll stop yelling at me. You’ll take it silently, just like Chris did. Totally mine. And then I’ll encase your body with mine, and we’ll be one. The submissive you and the dominant me. Only then can you work here with me and be my assistant and an acceptable bottom to my top.”
“OK, OK, I’ll try,” he whimpered. “I want to be here. I want your cock inside me. I submit. Totally.”
And I did, indeed, feel the tension slowly leaving his body, and he went silent, except for a few grunts and groans he couldn’t suppress, while I pushed the last three inches of leather and stud augmented penis into his tightened asshole. I left it in there, all the way in, for several minutes as I felt the tension and fight draining out of him.
“Now, would you like to try the real fuck I’d intended, me the total master and you the total supplicant?” I asked him.
“Yes, please,” he said with a new submissive tone to his voice.
I pulled my enhanced cock out of him then, and removed the sheath. Then I covered him in the way that brought me maximum pleasure and sexual release. I put my legs on either side of his and brought them in close. I reentered him with my unsheathed cock several inches and laid down close on top of him, my belly against the small of his back and my chest pushing into his shoulder blades. I wrapped one arm around his torso and played with his nipples, while the other hand went to his belly and, as my bare cock steamed slowly up his ass passage, lowered to his cock and balls. I nuzzled his neck with my lips and teeth and brushed the rough leather straps criss-crossing my chest on his tender back. Then I moved my head until I was cheek to cheek with him. I could feel the tears he still was shedding. I stroked his cock, pumping him to an ejaculation while, once my cock was in him to the hilt, I began slowly pumping him with my own cock.
He was loving it now, now that the fight was out of him and now that he felt the pleasure of my body totally possessing his. If Chris had told him how good this could be for him, he hadn’t been listening. If he’d realized, maybe he wouldn’t have fought me for control. But he was young and cocky, so maybe this had been inevitable.
“Oh, God, yessss,” he was whimpering. “Fuck me. Fuck me deep. Like that. Yessss. Don’t stop.” And I didn’t stop, at least for several minutes. A few minutes after he had spilled his seed on the carpet behind my desk, I shot my load into him. He was totally mine now--or so I thought, not fully understanding the nature of arrogant youth.
* * * *
Jimmy, Round Two
I reached up and released the tie that had held my assistant, Jimmy’s, head in place on my desktop and turned his head so that we could kiss. I laid there, his arms and legs still tied off close together through the kneehole in the desk, closely encasing him for a good twenty minutes, fully intending to fuck him again, to get my rocks off again, before I released him. I wanted to see those green eyes floating in semen. I was testing him, waiting for him to ask to be released, and then in one more assault on his asshole, I’d teach him once and for all that it was over when I said it was over. But he didn’t say anything. Maybe he understood what total submission was now.
But, then, maybe not, because I whispered in his ear. “Are you totally mine now? Can we move forward with no more of this nonsense from you, or are you out on your rear from this job?”
“Yes, yes, I’m totally yours now,” he whispered back to me. “I want you now more than ever before. But only if you throw that nasty penis sheath thing away.”
Ah, now, this wasn’t being totally submissive. So, I would take that last fuck, and then maybe another one after that, if necessary, but it wasn’t going to be the fuck that I’d anticipated.
With a sigh, I pulled out of him and picked up the expander sheath I’d penetrated him with before. I strapped it onto my penis and then I enfolded Jimmy once again in the close body meld that turned me on and fucked his brains out at ten and a half leather- and stud-augmented inches. He understood where he’d gone wrong now, at last, and he took this fuck quietly and stoically and said all of the right things when it was over.
But he was right about one thing he’d said in the beginning of the evening. When I was finished, all tension had left me and I was able to release him from the desk and get back to my computer. I wrapped up a winning proposal in short order.
While I was finishing up my work, Jimmy moved around as if in a trance, picking up his clothes and padding off with a bow-legged gait to the men’s room to clean himself up. When he was back together, he returned and asked me if he was needed any more this evening. I instructed him to sit on the sofa in my office and wait until I released him. He sat without question or complaint. A good sign.
I was still naked, except for my dress shirt draped from my shoulders over my now-exposed leather body strapping and my shoes and socks. But I’d come out of the last fuck so invigorated and so sure now of where I wanted this proposal to go that I had just plopped down and began to work my computer keyboard. More than an hour later, I pushed the save button one last time and stood up and stretched. I felt really good, full of energy. A good job done.
I looked around and there sat Jimmy, waiting for me to release him for the evening.
“Stand up and strip,” I said.
Jimmy started to say something, but then he remembered that we were having a little lesson in domination. He stood and stripped down again. He still looked beautiful. There was no sign of the ordeal he’d gone through earlier in the evening.
“Stand over there, in the center of the room.” He followed my command.
I picked up the blind cord and the tube of lubricant and walked over to him. “Down on your knees and open your mouth to me,” I said. He did so, and reached for my cock. “No,” I said. “I just said to open to me, not to show any signs of control. Hold perfectly still. And raise your wrists to me.”
I tied off his wrists again and pushed them to his back. I pushed my cock into his mouth with one hand and then I took his head with both of my hands. “A lesson of control,” I said. “I control everything. You control nothing. All you are is a warm, wet chamber for my cock. Just be warm and wet and open to me. Leave the rest of the control to me.”
And although he couldn’t help gagging a bit, he tried to comply fully with me. Maybe he had learned what I demanded.
“Now go tighter. Touch me closely on all sides.” That wasn’t as hard to do as it sounded, because I was so thick and long. I had taken that bag strap I’d used on Chris in the bar out of the my jacket pocket and now I fisted the two ends of it and lassoed it over Jimmy’s head, letting the padded part rest on the back of his neck. Using that as a control, I had pulled his face into my crotch and he had opened his mouth over my cock. Using the strap as a control, I pumped his head back and forth on my cock for a few minutes, checking his obedience, which was total, and getting my cock hard again.
Then, releasing the tension on the strap and pulling out of his mouth, I said, “Go down on your back right here.” Jimmy rolled back onto his butt and then on his back without comment or objection. I went down on my knees between his thighs and pulled his butt up on my thighs. I brought his hands over his head and back to his front.
“Now, I’m going to fuck you again. And, as I work my way in, I want you to jerk yourself off. And I want you to come when I’m in to the hilt, and not before. Understand?”
Jimmy nodded, a serious look on his face. I slathered my dick with lube, guided it to his asshole, and rotated it around, working it in, while he began to stroke himself and pull at his balls with his bound hands. I could see his mind racing on how he was going to ejaculate on cue. Good. He hadn’t questioned the instruction.
I slowly worked my way into him, as he pulled on his cock. I was closely watching the tension build in him and managed to be at eight inches inside him when I said “Now” in a raspy voice and he shot his load up my belly. As he ejaculated, I went in the last half inch. I looked down at the white globs of semen running down my black belly hair and perched on top of his golden-red pubic hairs. I liked what I saw, but this wasn’t the turn-on for me. The show of control and the use of the leather strap was turning me on, but I’d need the closeness the merging of bodies before I could reach an orgasm.
“You realize this was just for instruction, don’t you?” I said. “I was the one who controlled when you fulfilled this task, not you. Even though you thought this was your responsibility. It wasn’t. You realize that now, don’t you? You realize that I held off filling you until you had come.”
“Yes, sir.” Jimmy answered meekly.
“And you know now that this isn’t all that I want, don’t you? Chris learned quickly. How quickly can you learn?”
“I can learn quickly, sir,” Jimmy answered quietly. “I want you inside me. And I know that you want closeness, tightness as well as submission and control. Is that right?”
“Yes, that’s right. I’m going to unbind you now, and I’m going to fuck your lights out right here and in this position, and I want you to show that you can handle the tightness and closeness without the bonds. Chris showed that he could. Let’s see if you can. You will know when you succeed because your insides will be bathed in my cum. Do you want that?”
“Oh yes, please, sir. Flood me with your cum.”
I untied him then and enfolded him in my arms, belly to belly and nipples to nipples. His curly red chest hair tickled my pecs. I wrapped my arms around him tightly, holding his back down on the floor. I was pleased when he wrapped his arms around me as well and held me tightly, almost taking the breath out of me with his strong arms. His legs wrapped around mine below my buttocks and he pushed them in toward my legs as strongly as he could, holding me tight and tightening his ass canal as much as he could around my already-buried cock. We kissed deeply and then he buried his face in my neck, trying to pull himself into me at every point as much as he could. I felt the sexual urge flood into me, and I pumped and pumped and pumped at various levels, sometimes pulling out to give his prostate attention. He moaned and trembled at this but continued to hang on to me as tightly as he could.
When I came, flooding the very center of him in spasms of semen, he ejaculated again himself and collapsed back on the rug, arms and legs askew.
“Sorry,” he murmured. “It was just too much. I couldn’t hang on any longer. I’ve been royally fucked. This is the greatest.”
“Do you want me to pull out of you now?” I asked.
“Whatever you want,” he answered quietly. “You are in total control. Do what you want with me.”
Good choice. “Well, I want to lay here inside you a bit longer, so tighten up those arms and legs again.” He did so, right on cue.
After we’d gotten up and both cleaned up again in the men’s room, I told Jimmy to straighten up my office while I tidied up my desk. When we left, I told him we’d use the stairs rather than the elevator. It was twelve flights, but he didn’t utter a peep; he just followed me over to the door to the stairwell.
On the sixth-floor landing, I told him to stop and face the banister. He did so without question. I came up close behind him, unzipped my fly and pulled out my shaft. I doubled him over at the waist on the banister with one hand, so that he was facing down the well from the sixth floor, and I worked up my cock again with the other hand. When I was satisfied that I was at least half hard and able to penetrate him, I pulled his pants and briefs down off his buttocks, pushed his legs out to open him up as much as possible under these circumstances, and pushed my dick into his hole.
I took out the leather bag strap, fisted the two ends, threw it over his head and down to where his lower belly was resting on the padded part, used it as a sling to move his channel back and forth on my cock. I wasn’t fully hard yet and he’d been plowed several times already this evening, so I went in rather easily even in a dry fuck. He grunted and gritted his teeth as I entered him, but he grabbed down for the banister slats with white-knuckled fists and took me without comment or objection.
Once in, I tightened him up by getting his legs between mine. I draped my chest over his back so that we were both folded at the waist over the banister and facing down six flights of stairwells. I latched onto one of his ear lobes with my teeth and held on gently. I covered his fists with mine, holding him as if he once more were bound.
I could feel him grunting and groaning, and then sighing and moaning in ecstasy as my cock lengthened and thickened inside him and filled him once more to capacity. I had made this stop as a further lesson, teaching him to submit to me whenever and wherever I wanted, but I found this place and position, using the strap as a sling and letting my cock rise within him, even more sexually stimulating than the fucks I’d performed on him earlier in the evening.
As I filled him to the end and started to pump, I dropped the sling and took one of his fists and pushed down the front of his pants and we stroked him off together, his hand under mine, encasing his cock, while I controlled the stroking. As I sensed I was coming, I let loose of his earlobe with my teeth and started tongue-fucking his ear. He held his head closer to my tongue, loving the sensation. Once more we managed to cum almost simultaneously, me deep inside him and he down those six floors of stair well.
“Wow,” was all he could say when it was over.
“Yes, wow,” I responded. “Now how do you feel about needing control?”
“I’m completely yours. Do what you want with me wherever you want to do me.” Again, the right answer.
We left the building, and Jimmy gave a little wave, saying he’d see me the next day, and turned from me to walk down the street away from me.
“You’re coming with me,” I said. “Here’s my car. Get in.”
Without hesitation, Jimmy walked over and got in the back of the limousine that was waiting for me at the curb. My burly chauffeur held the door for him just as if this was the most natural thing he’d seen. He and I had already had our innings on the point of who was in control.
We were a good twenty minutes out, cruising to the edge of the city and beyond, when I turned and instructed Jimmy to strip again. I could tell that his instinct was to look toward the back of the chauffeur’s head and to say something about the presence of another man, but he gained control of himself in time and proceeded to strip. While he did so, I unbuckled and unzipped my pants and took them off and set them aside. I didn’t remove my coat, but I unbuttoned my shirt and pulled it open. I’d be wanting to feel the closeness of skin on skin. I stroked my cock briefly, but I took the cue from the stairwell and didn’t wait for it to fully harden.
“Sit down on the floor,” I said, and Jimmy sat down on the commodious backseat floor, his back to the bench seat. I went down on my knees in front of him, took his head in my hands and told him to open his mouth to me. He did so, I maneuvered my cock to his lips, and then I face fucked him for a couple of minutes. Just long enough to get my cock good and wet with his spit. Then I turned and sat back on the center of the bench seat and told him to sit on my lap, facing me. He did so. I leaned up and I told him to put his arms around me between my skin and my shirt and jacket and to wedge his fingers between my skin and the leather straps criss-crossing my back. Then I leaned back, trapping his arms around me and plastering his chest to mine. I lifted his hips and lowered his ass onto my half hard on, making the entry easier because my cock was slathered up with his spit and because I wasn’t fully hard yet.
I rocked back and forth, my dick lengthening and thickening inside him. I didn’t feel the strong sexual urge yet, but I was about to fix that. Jimmy had passed the test of being fucked in front of another man. We’d now see how up and close he could sustain this obedience.