My Boss Is A Bastard

"Bastard!" That's me talking to my boss. Well, he's not really my boss; just someone I work with sometimes. But he is a lot older than I am and sometimes he treats me like he is my boss.

My name in Jessie, and I'm a 26-year-old program assistant, with a newly-minted PhD in Political Science. I work at an advocacy organization, and this is my first real job out of school. I'm smart, and I'm driven to be the best. I graduated top of my class. I have very little social life, having spent the last seven years immersed in study, and no hobbies except football, which I play ferociously three times a week. Blond hair and blue eyes, I'm very fit, and considered attractive, although I must admit I haven't had a steady boyfriend since high school. Just too busy.

"Asshole!" My boss John is ancient. In his 50s at least. He's a senior manager at our organization, and is the only other person who regularly works at the office on Saturdays. Over the past three months we have developed a friendly, bantering relationship, at least on Saturdays when no one else is around. We argue and joke about everything; politics, religion, and football (he is a Newcastle United supporter). He is very politically incorrect and constantly trying to wind me up. Today we were arguing about nature versus nurture and gender roles.

"Women will never be leaders," John said, "because they are naturally subservient. It's evolution—a survival trait. Women are very vulnerable when they are pregnant or raising small children, and need protection, and over eons those that were subservient and submissive to men were most likely to get that protection, and survive to pass on the trait. Deep down every woman wants to be submissive, and will only feel secure when she is."

"Bullshit! You are so full of shit!" I'm a strong, intelligent, independent woman, and I knew there must be a fallacy in this argument. I wasn't sure what it was, but I wasn't going to give an inch. "Men and women are the same. Some may be leaders, and some followers, but that depends on nurture rather than biology, and it could just as easily be the man that is submissive."

"Jessie," barked John, "go get me coffee!"

I was dumbfounded for a moment by the direct order. "Fuck you!" I replied, when I finally recovered.

"Ah Jessie," John said with a smirk, "I noticed your hesitation. For a moment you almost complied. Deep down you wanted to, and would have been somehow fulfilled if you had. All women feel the need to be dominated by a man. It's their nature."

I knew he was wrong, but this argument gave me a weird feeling in the pit of my stomach, and an uncomfortable hollow feeling between my legs. With nothing else to say, I muttered "Asshole," and went back to work. Later at lunch we argued football, and that is where I made my mistake.

"There is no way Newcastle can beat Manchester! Never gonna happen." I said, with some heat.

"Want to put a wager on that, little bird?"

I hate it when he uses those stupid pet names. "Sure," I said, "put your money where your mouth is. I could use twenty pounds."

"Okay," he replied, "but let's make it interesting. If Manchester wins, twenty pounds. But if Newcastle win, you have to serve me coffee and lunch and take care of me on a Saturday. In other words, be submissive. If you can do that all day, and still disagree with my theory by the end of the day, I'll give you the twenty anyway, to pay for your extra work."

My initial thought was to tell him to fuck off, but there really was no way he could win. If Manchester won (very likely), I would get the twenty, and if Newcastle won (inconceivable), I might have to serve him coffee, but I would still get the twenty, and I needed some extra cash. After a momentary pause, I said, "Okay, you are on!"

"No, no, no, please god no!" I was watching the game at home, and it was crappy and scrappy, still nil-nil at 90 minutes, but Newcastle had just won a penalty, and after a pathetic performance the entire game, their friggin striker put it in the top corner. I had a sinking feeling when I realized I would have to humiliate myself with the jerk, but consoled myself with the thought that at least I would get the twenty.

The next day at work, John was insufferable. Every time I walked past his office he would yell something like "Newcastle forever!" or, "Man U suck!" Everyone in the office knew we had a bet on the game (although not the details), and started to tease me as well. Later, when I passed him in the hall, he stopped me, and leaning close said, in a low voice, "Don't forget, you will be serving me this Saturday."

"You're not really going to make me go though with that are you?" I asked, hoping for a reprieve.

"A bet is a bet," he replied, "and I want you there at 8:00, ready to serve. And wear a dress. I want you to look ladylike, for once."

"Hurmff!" The nerve of this guy, adding conditions. I was too upset by the teasing of my co-workers, and his taunts, to respond, and spent the rest of the day at my desk scowling, avoiding everyone.

During the week my mind often drifted to Saturday, and I would get that hollow feeling in my lower stomach. Butterflies, I thought. Natural, considering my situation. Still, I would make the best of it, get it over as soon as I could, and promised myself to use the twenty for a special treat, to compensate for the shame.

The week passed slowly, but Saturday came all too quickly. Normally I wear slacks and a button-down oxford to work, but that morning, after much internal debate, I did choose a dress. A frilly white summer frock. I don't know why, but told myself the ordeal would be easier if I didn't start on a bad note. Since I was dressing up, I also spent a long time going through my underwear drawer, selecting the best from my limited selection of mostly utilitarian briefs, a sexy silk set my little sister had bought me as a joke birthday present.

When I got to work John was already there, and of course, no one else was around.

"There you are," he said, "and you're late. But at least you obeyed my first order, and wore the dress. Very nice."

"Hey," I replied, "I didn't wear it for you, I just felt like it."

"Okay. Whatever. Now bring me coffee."

"Asshole," I muttered under my breath, but I went to make the coffee. When it was finished, I went back to his office. John was sitting on the sofa in his office, reading the paper. I slammed the cup down on his desk and, with bit of venom, said, "Your coffee."

"Now, now Jesse, we had a bet, and I expect you to pay up in the spirit of the bet. Pick up the cup, bring it over to me, then kneel and offer me the cup in a subservient and submissive way. That's part of the bet!"

"Oh, fuck you," I said. "You are not really going to make me do that are you?"

"Knees." was all he said.

By then the butterflies where shaking my insides, and I almost walked out, but finally I turned around, picked up the cup with exaggerated care, turned and knelt and said, with sarcasm, "Your coffee, oh lord and master."

"Better, much better. But I prefer you just call me sir," he replied smugly.

I rose and left, confused and ashamed, feeling a blush burning my cheeks. That prick was going to force me to fully honor the terms of the bet. That bastard. That asshole. I was shaking a little as I walked back to my desk, whether from anger or something else, I don't know. I tried to concentrate on work, but my mind kept returning to the feeling of the carpet on my knees.

Three times he called for coffee before lunch, and each time we went through the same ritual, but with each episode I was less sarcastic. There didn't seem to be much point, and I just wanted this whole experience to be over. By 11:00 I couldn't concentrate at all. I sat, squirming a little in my chair, consumed with anxiety and dread, expecting at any moment his next demand.

Suddenly I realized that through the nervous squirming I was rubbing my bottom against the seat, and there was some heat down there. With dawning horror, I realized that our little game, our charade, was starting to arose me. No, it couldn't be, I thought. I'm a proud and independent woman, in command of myself and my own destiny. The thought that I liked being submissive was too much.

"Jesse, come here!" John called from his office.

I wasn't angry anymore, I felt nervous. This whole situation seemed to be getting out of hand, out of my control. I got up, feeling timid, and went to his office. "Yes?" I asked.

"Yes, sir," he replied.

I didn't want to, but I was tired of the struggle, and answered, my eyes downcast, "Yes, sir."

"Good," he said. "I think you are ready for the next step in our little test. Come here and kneel next to me."

"Why?" I asked.

"Don't ask questions. That's part of the bet. Just do as you are told," he softly said, as if reasoning with a child. But his next words he barked, with steel in his voice, "Now come here, and kneel!"

I was startled by his tone. This was getting too serious, and I needed to get out of it. And yet, as I had the thought, my feet were moving, and before I completed the thought I was kneeling before him.

"Now, down on your hands," he said, and I did, this time without a word. I think I didn't want to, but at this point it was almost as if I was no longer in control of my body. He spoke, and I responded, like an automaton. My breath came rapid and shallow, almost like a dog panting. And then he touched me. He laid his hand on the white cotton dress covering my rear, and it was like an electric shock went through my body, and I shivered.

"What are you doing!" I said, in a panic.

"Now, now," he said, "don't be nervous. This is just the final part of the test."

As he spoke he was patting and rubbing my rump, as if calming a nervous horse. "I just wanted to demonstrate that deep down, like all women, you want to be controlled. Think about it, you are on your knees, and if you are honest with yourself, deep down you like it. Admit it."

"No!" I was confused and surprised. This was so wrong, but there I was, on my knees. "No, this is wrong." I said. I started to get up, but he reached out with his other hand to grab my neck and hold me there, on hands and knees.

"Stay! Just five more minutes," he said. "If after that you still disagree, we will be finished. I'll admit you are right, and you will get the twenty." I had been pushing up against him, but with that I released the tension in my back and settled again into the carpet, which was starting to irritate my knees.

"Five minutes, that's all, then the money," I said. I didn't know how I could stand five more minutes of this degrading treatment, but at the same time some part of me did feel okay, comfortable and secure. But I would never admit it!

One hand was still laid gently on my neck, while the other had begun massaging my buttock, and then lower down my leg. "Shhh... little one," he said, as he continued his massage, fingers kneading my neck and the other hand working the big muscle of my thigh. "That's right. Enjoy it. The more I control you, the better you feel," and dammit, I was starting to enjoy it. It had been a long time since I had felt the touch of any man, and he clearly knew what he was doing. Still, if he thought a massage was enough to convince me, he was dreaming. I could see my watch, and I was counting down the time.

Just as I was thinking this would all be over soon, his right hand started working up my leg, and under my dress. "Stop!" I yelled, and again tried to get up, but he didn't stop. He moved his hand between my legs, and placed it directly over my silk-clad mound.

"Stop it!" I yelled again. The growing calm I had been feeling was gone, and now I was in a real panic. I kicked my legs, trying to get up, but as he had grabbed me below, his other hand had wrapped around my neck, and I was trapped, unable to move. "Don't, please don't!" I begged, as he began to rub me down there, and I realized, to my horror, that my pretty silken panties were soaking wet.

And he noticed. "Mmmm, very wet," he said. "I think your body is telling you, and telling me, that deep down you want to be subservient. You want to serve me, obey me, because that is the only way you can be content, be a real woman." And then, to add insult to injury, he chuckled—the bastard actually chuckled. "I think," he said, "I will win my bet."

Suddenly, I was more angry than scared. "Fuck you, you asshole!" I screamed, struggling to get loose, but he shifted his grip from my neck to my hair, grabbing my ponytail and using it like a handle. "You fucker! I'll.. I'll.. unnghhh..." As I was screaming, he had slipped a finger around the elastic of my panties and straight into me, and began working me, pulling me by my hair back on to his hand.

"Noooo... please, no!" I pleaded, but the joking old man I knew was becoming rougher, and harder. He took a firmer grip on my ponytail and turned and pushed me on to the couch, and held me down, so that my breasts and face were crushed against the warm, brown leather. I kept struggling, but he was simply too strong, and as he held me down with one hand, he pulled my panties down to my knees. My face pressed into the couch, I couldn't speak, but went wild trying to escape.

"Oh, Jessie, settle down now," he said, "you have wanted this for a long time."

And then I heard the sound of a zipper, and rustling of clothes. He moved around behind me, maintaining his grip on my neck and back, and then I felt it. Like a heavy, fleshy, spongy stick bumping against my thighs. I knew what was coming then, but still tried to resist.

"Stop, stop, don't do this," I pleaded, but as I spoke I could feel his stick moving up to the intersection of my legs, and then rubbing in and out. Its trendy these days for women to have a thigh gap, and as a fit athlete, I have a big one, but even with my legs spread as far as my silk panties would allow, his stick filled the gap, and pushed hard against my thighs. He would not have been able to push it through at all had the gap not been liberally lubricated already by my own traitorous body.

"Feel that Jessie? That's my big cock. That's going to be deep inside you soon. Are you ready for it?"

"Please John, don't do it! Please, please, oh no, please!" I begged, "I won't tell anyone, please no..." I was really terrified then. I was shocked by his language, and I'd only had sex a few times in high school, and my boyfriend's penis was much smaller than this massive thing. It would kill me, I was sure. He kept going in and out, dragging the head of his massive tool back and forth across my engorged and incredibly sensitive clitoris. Oh god help me, but full of fear, I still found this disgusting asshole was sparking some primal and unconscious and uncontrollable physical reaction in my traitorous body.

"Feel that baby. You know you want it. Say you want it. Say you want my fat cock in your pussy. Say it!" he demanded, as he pulled back on my ponytail, stretching my neck.

"Fuck you, you bastard!" I screamed in rage. But I did feel something. I didn't want to admit it then, and I don't want to now, but something inside me was responding to the friction. Then I felt the tip of his stick, his cock, stop next to my entrance, and slowly start to push in. "Ooohhh...nooooo...uhh, uhh, please...stop...". Only the very tip, and already I was stretched uncomfortably wide.

Unconsciously I tried to spread my legs (which were constrained by my lovely silk panties) wider, to reduce the pressure from his massive meat, and as he pushed, I heard my panties tear, and my legs spread of their own accord as far as possible. It wasn't enough.

"That's it baby. God, you are so tight! So wet! Come on, take that meat in your little pussy," he said, as he continued to slowly and relentlessly push the head of his cock inside me.

"Unnnngh...mmmmph...ooohhh..." I felt like I was being split in half, impossibly full, incredibly painful. I started crying then, uncontrollably. "Please... oh god... no... please, it hurts... oohhh."

"Relax, you will be used to it soon. But you will never be the same again, little girl."

"Stop... please, stop... ohh god omnagh ohh." And he kept pushing. I couldn't believe there was more, I thought I would burst, but more there was, pushing, pushing, pushing. Finally, he gave a groan to match my own, as his cock stopped against my cervix.

"Oh so good, so tight, so sweet," he hissed. "Relax baby, just relax," he said again, and slowly started to pull back. It was a relief, but also created a hollow void, a vacuum and yearning, trying to pull him back inside. And when he was almost out, he started pushing forward again. Then back, then forward. In and out. As he settled into a rhythm, it got easier, although I still felt completely stuffed, the initial pain receded. Amazingly my body was adapting to him, and all on its own started reacting to his thrusts, at first moving to avoid them, but eventually falling into his rhythm.

"That's it baby, now you feel it." And I did. My body was responding to his vicious assault, his violation, and I was experiencing sensations I'd never felt before.

"Oooh ahh, ummgd..." I babbled incoherently. In the back of my mind I realized he was no longer holding me down. His hands had shifted to my waist, and he was controlling me from there, driving me like you drive a motorcycle. And with each minute of his relentless pressure I became more responsive to his control, leaning in to the curves, and jumping as he opened up the throttle.

"Oh my god!! Oh fuck! Oh..oh..oh...oooh." My whole lower body was numb, but at the same time super sensitive, sparkling with electricity, and the sparkle was entering my brain. I was defeated, and yet released. Using all my energy struggling to keep up with John. I was very close to orgasm, something I hadn't done without a vibrator for years, but if those previous orgasms were akin to a balloon popping, and then slowly deflating, this felt like a dam on a mighty river about to give way.

"You like it now, don't ya, you prick-teasing bitch. All those months of teasing me, with your perfect tits and perfect ass. Now you know who your boss is."

The last vestige of the rational me grunted, "No... fuck you, no.. uh..." but I knew it was over. He grabbed my ponytail again, pulling back painfully.

"Say you want this! Say it!"

"No... you bastard... you fucker... you prick... no... ohhh," I could feel the dam about to burst. "Oh god...noooo.. oh, please, oh, yes... oh my god, yes... yes..." And he stopped. One hand still on my ponytail, and one on my waist. But he stopped. Caught up in the moment, and very close, I kept moving, trying to keep up the rhythm.

"Stop!" he commanded, and shocked, I froze, at least as much as I could. The walls of my vagina, driven by the primitive and unconscious part of my brain, continued to squeeze and pulse. "Don't move!" he ordered again. "Now ask me to continue, no, beg me. Beg me not to stop, you teasing bitch."

What was happening? What was he doing? I needed this. "Fuck you!" I yelled, from a place of deep frustration and anger. And then he wiggled just a bit, and I surrendered all at once. "Okay...okay... yes."

"Beg me. Beg for it."

"Oh fuck, you fucker, please, please," I squeaked.

"Please, sir," he said, and I responded, pleading now.

"Yes, sir... please... please, sir." The pulsation in my vagina had moved to my hips, and although I tried to stay still, I couldn't control it.

"And you agree that women were made to serve? That you were meant to serve me?" he asked.

And there is was. The final degradation. Laid out starkly for all to see. But there was not struggle, only acceptance. Acceptance of the rightness of this, and the knowledge deep down inside me that this, for me anyway, was right.