Putting the Boss in His Place

Working for Kevin sucked. His branch office was one of the insurance company's most productive, but he got those results by being a hard-ass to the people who worked under him. His reputation as a tyrant was well known, so I was not pleased when I learned that I was being transferred to his unit.

It's not that Kevin intimidated me—he didn't. I knew I was good at my job, and I also knew I wouldn't be working for him very long. I was taking night classes and would be getting my MBA in less than a year, and that degree would launch my career right out of his department. Plus, I wasn't the kind of guy who got intimidated easily anyway. Standing six-foot-three, I was 27 years old at the time, with a strong build and a confident way about me, and I wasn't about to cower at the idea of working for someone like Kevin. He was about ten years my senior and definitely an alpha male—very driven and aggressive, a former Marine with a muscular, six-foot frame—but I didn't fear him.

The first week in Kevin's unit was an adjustment. I watched as he relentlessly pushed his people. The poor guy who sat next to me, a meek fellow named John, was always getting his work handed back to him with a long list of harsh comments. Kevin was often verbal in his criticism of John and the others, saying things out loud that could have been relayed privately with less embarrassment. There was one woman, Stacy, who often went to the ladies' room in tears after being lectured and humiliated by Kevin. He was just a classic asshole boss.

Surprisingly, when I joined Kevin's unit it wasn't so bad for me, since for some reason he rarely directed any mistreatment toward me. It was almost as if he kind of liked me. He would sometimes hand my work back with lightly critical comments, but nothing too outrageous. The emotional outbursts and hostility were usually aimed at the other employees. This was still no picnic for me, of course, since his toxic personality created a miserable work environment for everyone.

Then one day, after about a month in Kevin's unit, something happened that would become a milestone in my life, and his as well. It unfolded quickly, and as I look back on it I sometimes wonder if it was a dream. But it wasn't.

It had been a difficult day, with Kevin acting even more truculent than usual. I had recently learned that his wife was divorcing him, so that probably had something to do with it. I didn't know his wife, but I sympathized with her nonetheless, since I couldn't imagine living with such a prick. Anyway, that day Kevin had already unleashed on everyone else in the unit at least once, but as usual I had escaped it. That changed, however, at about four o'clock. To my surprise, I heard Kevin yell out my name, summoning me to his office, and not in a friendly or professional tone.

I complied, of course, and as I approached him he proceeded to rant about how my work on a particular file was inadequate. He didn't even look at me, keeping his eyes on the folder in front of him instead, but he was loud and obnoxious as he berated me and my work. There was no doubt that everyone in the area could hear him. He went on and on, saying I had been grossly neglectful, even insinuating that I was incompetent. He had never directed this sort of outburst toward me, and I was shocked. I was finally learning what it was like to be mistreated and humiliated by Kevin—and I did not like it.

But I stayed calm. At first I respectfully defended my work, knowing it was solid, but I decided not to be too zealous in my own defense. I felt that by seeming overly concerned I might give him some sense of satisfaction, so instead I mainly just let him have his tantrum. I was steaming inside—angry beyond description—but I held it together.

Returning to my desk with as much pride as I could muster, I could see the others avoiding eye contact with me, having been on the receiving end of such mistreatment themselves many times and knowing how awful it is. I tried to imagine what it must be like to put up with such unnecessary antagonism for years, as John, Stacy, and the others in the unit had. My ego would survive this—especially since I had an exit strategy with my MBA—but my blood boiled as I thought about what the others had to endure.

The work day would end in only a few minutes, and I spent that time replaying what had happened in my head, which only inflamed my inner rage all the more. At closing time, as usual, everyone in the office except Kevin got up and left. As the branch manager he often stayed late, and it wasn't very unusual for me to stick around after hours either, since my desk was a good place to do a little studying before my night classes.

That night, however, I wasn't staying late to prepare for class—I had other motives.

When I was sure that everyone else had left, I made my move toward Kevin's office. Still enraged, I approached him as he sat at his desk working. He seemed surprised to see me, but not shocked. When he saw the look on my face, however, he realized a confrontation was coming. He opened his mouth to say something, but I stepped toward him right away and took control.

"Don't you ever talk to me like that again!" I said to him sternly, staring him down. I was surprised to hear the words coming out of my own mouth, but unable to exercise restraint. He could see how serious I was. His mouth dropped at my aggressive tone, and to my delight I saw a slight look of fear in his eyes. There were a few seconds of silence as we both assessed the situation. In my head I replayed how he conducted himself every day, how he seemed to enjoy intimidating others, how he acted like such a big man, how he was such a goddamn bully. At the same time I realized that, unlike others, I was able to see through his charade. He could be physically imposing and intimidating to some, but I looked down on him and wasn't at all afraid. As I stood over him sitting there, I didn't see the powerful boss man that everyone else saw—I saw a pussy who needed to be taught a lesson.

I took one more step toward him, so that I was now standing within reach. I'm a big guy and I was in excellent shape at the time, carrying a powerful, athletic frame—and I was bullshit mad. Still sitting in his chair, he looked up at me with what looked like doe eyes. Meekly, he muttered only one word: "Sorry."

He looked pathetic, and he seemed to be waiting to see what I would do. To be honest, I had no idea myself. I was on autopilot, with no specific intentions as I entered his office—I just knew I needed to confront him, and that's what I did. Part of me wanted to punch him, but I knew I wouldn't and couldn't do that. Instead, I continued to stare into his eyes, and without thinking I reached for his face and grabbed his chin with determination. I tipped his head back just a few inches so I could look even more directly into his eyes, and with absolute confidence I said to him, "I don't take that kind of shit from anyone—do you understand?"

He tried to nod, but I controlled his head and didn't allow it to move. So instead he gasped, "Yes."

There was no doubt about the power dynamic here, and I was savoring it. I wasn't about to let it end. This jerk was responsible for so much misery to so many people, and I now had his chin in the palm of my hand as he sat helplessly before me. I could tell he was waiting to see what I'd do next, and I was surprised at his passivity. I knew I was in charge, I could sense his apprehension, and to my surprise I could feel myself getting aroused by what was happening. I had never thought of myself as gay—I love women and I love pussy—but something was happening here. Having Kevin submissively before me, I suddenly realized the awesome possibilities, and the blood began rushing to my cock.

I loosened my grip on Kevin's chin just a bit, and I let my fingers stroke his face. I could feel this five-o'clock shadow, and as I looked at him I considered all the times that he had bullied his staff. His eyes continued to gaze up at me, and I grinned slyly at him with a look of domination. It was then that I realized that he too was seeing the sexuality of the situation, and with that the rush became intense—nothing could stop me now from having my way with him.

I could feel the power growing in my crotch. I stopped stroking his face and grasped his jaw firmly again. With my other hand I unzipped my pants. His eyes moved to my groin as I did so, and he didn't blink as I reached in, grabbed my dick, and pulled it out directly in front of him. I was getting erect already, and the sight of Kevin helplessly gazing at my impressive manhood turned me on even more. He was staring at it, seemingly in awe, and I held his head triumphantly. He looked up at me for a moment, speechless, and I didn't have to say a word. Holding my cock, I moved it slightly in his direction and he obediently opened his mouth.

"That's it," I said as I felt his mouth close warmly around me dick. "That's exactly what you need, you fuckin' prick. You need a good mouthful of cock." His eyes were gazing into mine as I spoke. I backed away for a moment and had him get off the chair, onto his knees in front of me, then I returned it to him. "Now suck it good," I commanded.

With that, he obliged without hesitation, turning the full focus of his attention to my shaft. By now I was a fully erect, a rock-hard seven inches, totally turned on by the sight of my adversary utterly defeated before me, sucking my cock. I clenched the top of his head with one hand while holding my wide girth in the other, and I guided him up and down the pole. His eyes would occasionally look up at me, almost seeking approval, and I delighted as he followed my orders. I had him lick every inch, from base to tip, all around. Then I pulled away and slapped him in the face with my rod, nice and hard several times, only to quickly shove the meat right back into his mouth.

There is nothing more empowering that having your nemesis in total submission, leaving absolutely no doubt who is the real boss. I watched Kevin gurgle as he tried to fit my hefty rod down his throat. When I let up a bit so he could come up for air, he gasped and his saliva dripped all over his chin. It was pure victory. The poor guy was in shock, but at the same time I could see he was enjoying it. He had needed someone to put him in his place, and I was just the man to do it.

As he caught his breath, I unbuckled my pants and let them drop. This allowed him full access to my balls, and they wanted attention. "Lick them!" I ordered, grabbing his head and pulling it closer. He tucked his face underneath, letting my stiff meat rest proudly on his forehead as his tongue gently went to work on my sack. He was good. He stroked my dick with one hand while he used the wide swath of his tongue to massage my scrotum all over, front and back, repeatedly. The feeling of his wetness on my hairy balls was incredible. Then, like a good boy, he opened up and sucked on one ball, then the other, gently swirling his tongue around each as he did so. It felt fantastic, so satisfying.

Taking it even further, at my instruction he opened his mouth real wide and consumed both balls at once. Given their size, this was a most impressive feat, and I think I sensed a hint of pride from him when he achieved it. This was a moment I was going to relish, so I held his head up close to my crotch to ensure that his mouth stayed squarely around both balls. I could feel his lips in a full circle against the skin above my scrotum, and I wanted them to stay there. Once he adjusted to breathing through his nose, he got comfortable and settled down with the entirety of my sack stuffed in his mouth. The saliva oozed down his face while his tongue, crammed with a mouthful of genitalia, found ways to move around, tickle my balls, and pleasure me.

This was an unbelievable conquest, but I wanted more. Despite Kevin's impressive cocksucking skills, I still hadn't come yet. I pulled my balls out of his mouth and looked down at him satisfyingly. "Good boy," I said as he looked up sheepishly, my big dick bouncing in front of his face. I patted him on the head, and he humbly looked down. I then grabbed him by the hair, gently but firmly, so I could look him in the eyes again. He had a strange look of both fear and contentment. My dick was like a steel rod, just inches from his face, and it was telling him that there was still work to be done. I was in total control, and now I knew how I would finish this.

"Get up and drop your pants."

He hesitated for just a second, no doubt thinking about what those words meant, but then dutifully stood up and unbuckled. Without being told, he turned around, and I watched as his pants fell to the floor and he stepped out of one leg, allowing his feet to spread apart. Neither did he need to be told to bend over—he leaned over and rested his forearms on his desk like this was something we did all the time. Oddly, he had not dropped his underwear when he dropped his pants, so I did the task. "Don't be shy," I said smugly as I lowered them, revealing his tight, bare, athletic ass.

There is no feeling of conquest that exceeds this—having your oppressive boss in total submission, waiting for you to drill his ass—so I took a moment to appreciate it. Using my throbbing dick as a club, I spanked his pathetic butt a few times, enjoying the sound of my cock hitting the firmness of his ass. He looked good, having kept himself in shape, muscular and toned. The sight of my massive dick proudly soaring over him was an incredible turn on.

With him in the position, I guided the tip of my penis lower, allowing it to just barely touch his rectum. Kevin had been silent, but now I heard some muffled sounds coming from him. He was scared—and understandably so. As I just barely tickled his asshole with my tip, there was a slight gasp of apprehension. His only words were a soft whisper: "Please, don't hurt me," he pleaded.

I loved seeing him so helpless, such a contrast to the raging bully he was to everyone in the office. I was tempted to yell at him, to do something very rough, but my own selfishness restrained me. Our little session might end too soon if I got too rough too quickly. So I appeased him, not with words but by doing him very nicely, by treating him like my favorite girl.

As I slowly pushed my tip in just a little further, he got more verbal and made little squeaks and gasps as he adjusted to having a dick entering his ass. I moved in and out just slightly—just a fraction of an inch—and I could see that this little motion was enjoyable to him. He continued to make sounds, fear was laced with pleasure, and I smiled wide when he tipped his ass up in a way that let me know he wasn't objecting.

At that point I noticed a bottle of water on his desk, and it was just what I needed. I took it, pulled my dick away from his asshole for a second, and used it for lubrication. I wet down my cock, and I gave his crack a squirt as well. Now everything was moist, and I was ready for business. I proceeded slowly. The tip of my stiff rod returned to his hole, and this time I could feel the wetness. I pushed in and out many times, still with just the tip, but with larger and larger portions of it, slowly widening the hole. I held him by the waist, in complete control of him, as my rock-hard dick began the penetration. I was getting so turned on, but not as much as him. He moaned and moaned, louder and louder, absolutely loving it. His entire body collapsed on his desk, his hands sprawled out, as I held him firmly and entered him. I eventually got the entire head of my dick in, and at that point I stopped for a minute.

There I stood, plugged into my boss as he lay helpless beneath me. It was only then that he turned around, looking over his shoulder back at me, with a terrified look on his face. He had no words, but he didn't have to say anything. Seeing his face reminded me of who I was fucking. For a few minutes I had gotten lost in the pleasure of the sex, almost forgetting who I was with. But now I saw Kevin's face peering back at me in a state of shock, knowing that I was his unquestioned master. For a moment it almost looked like he was asking if, given the situation, we were friends now. But I still despised him, and I couldn't throw him the look of a friend or a lover. I could only look at him blankly as I applied more water to his asshole, which now had my dick protruding from it. "Get ready," I warned, putting the water down and placing my hands on his narrow hips.

I slowly pushed in, a fraction of an inch at a time, occasionally backing out a bit before returning to go a bit deeper. Kevin cried out from the start, in pain and ecstasy, and never stopped. I kept him well lubricated as I methodically penetrated deeper and deeper. It a fantastic fuck for both of us—my dick seemed to get even bigger as I got more turned on, and he was like a bitch in heat, absolutely lost in the moment and totally into it. "Oh my God!" he cried out repeatedly, in between loud moaning that seemed to find new octaves.

Finally, after some time, I was all the way in. I was standing behind him with my entire length, right up to the base, buried deep in his ass. His upper body was flat on his desk, his rear end was angled up to accommodate me, and his feet were wide apart on the floor. As he lay there I couldn't see his face, but I could hear him sobbing lightly.

"Who's the fucking boss now, Kevin?" I asked. I gave my hips a gentle shake, and when I did my manhood, burrowed deep inside him, moved his entire pelvis.

"You are, sir," he replied, sounding exhausted.

"Let me see your face," I said. He turned his head and I again saw his impressive features. He was a strong, good-looking guy, with a straight Roman nose, full eyebrows, strong eyes, and narrow chin. I was extremely proud of myself for conquering him, and I somehow felt that what I was doing was vengeance on behalf of all the people that he had bullied for so long. I looked him in the eye and said, "You know you deserve this, don't you?"

"Yes, sir," he replied, sounding like the good soldier he once was.

With us both having enjoyed the process of getting the full length of my dick planted in his asshole, I was now ready to really fuck him. I held his hips and began, starting with slow and small movements. He continued to look back at me, and I looked straight into his eyes. As soon as I started, he began a constant moan that halted only for an occasional scream. I sped up the pace and increased the lengths of my thrusts, until eventually I was pounding against his ass and drilling him mercilessly. I plunged my dick into him repeatedly, feeling the tightness of his asshole all the way up and down my shaft, over and over. He was crying out uncontrollably as my cock pierced him like a lance. It was absolute insanity as we lost ourselves—I totally owned him and his asshole.

Eventually I pulled him back away from the furniture so I could bend him over further, and when I did I could see that he had come on the desk. I looked down and his dick was still hard, or perhaps it had gotten hard again after the first orgasm. It was small and unimpressive. No surprise.

By now I felt like I was ready to come soon too, and the question was how. I wanted to come in his ass, but I also wanted to make sure that he got a good mouthful of my jism. The solution was timing. I bent him way over, so he was just about touching his toes, and began drilling him again, slapping my body against his butt cheeks to ensure that he took every bit of me. I pulled out and admired the wide hole that I had created—a perfect depository for my semen.

I entered him again, found a good rhythm, and could feel the climax getting close. My dick was absolutely throbbing and ready to explode. I knew the load would be huge. I pulled out and tickled Kevin's bored-out asshole with the tip of my dick, until the surge became irreversible, at which time I plunged deep several times. Kevin and I were both screaming as I climaxed in his asshole, but then I quickly pulled out and spun him around again into a kneeling position in front of me. The juice was gushing from me, and I gave him a several good squirts in the face. I then stuffed my cock in his mouth, letting it pulsate as the semen drained out of me. It took quite a while, and the white stuff was everywhere, in his hair, all over his face, even his neck and shoulders. Best of all, it was oozing from his mouth. The sight was spectacular.