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?"
