My Boss is a Bastard–John Responds

After I wrote my first story, I showed it to John, and he said that from his perspective, it hadn't happened like that at all. I was curious, and encouraged him to narrate events as he saw them, and he agreed. It has taken a while, and he made me write it up (of course), and while I tried to tighten his narrative and tone down the language some, he has approved this version. I hope you enjoy it. -- Jessie

"Bastard!"

That's my assistant, Jessie. She came to work for us fresh out of university, and has been driving me mad ever since. Jessie is earnest, idealistic and certain of everything, as only twenty-somethings can be. She pretends to be a tomboy, one of the guys, talking football and wearing chinos and button down oxfords, but to me she is just a tease. Her trousers are low cut and tight, designed to show off her curved and athletic ass, and her flat belly. Her shirts are unbuttoned enough to show off the rounded tops of her firm breasts.

"Asshole!"

Jessie was upset because I told her women are naturally subservient to men. To me this is self-evident, a product of evolution, a fact that all thinking people would (or at least should) acknowledge, but I knew that in the modern, hyper-politically correct, world, it would set her off. I didn't care.

It used to be I had Saturdays at the office to myself, a peaceful time to catch up on email, and to write; but lately Jessie had taken to demonstrating her zeal by working on Saturdays too, seemingly just to irritate me. Don't get me wrong. I enjoyed looking at her, and wasn't above engaging in a little innocent teasing myself, but she did upset my settled routine. That morning Jessie was particularly provocative, bending over to get files to show off her ass, and leaning towards me as she spoke, making it impossible to see anything but her fresh young breasts.

Not that I could do anything about it. Truthfully, I guess, I was in a bit of a rut, and had been since my wife and I separated after the kids went off to college. Although I still get out for the Sunday pub league, I lacked the vigor and enthusiasm of youth, and seemed to be just seeing out the days and years till I could retire. Having Jessie around to tease was entertaining, but also a little depressing, knowing that the enjoyment of such fine young stuff was my past, not my future. Anyway, back to the story. In response to her shouted insults, I struck back, responding calmly and using reason.

"Women will never be leaders," I said, "because they are naturally subservient. It's an evolutionary survival trait. Just think about it. 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 to survive to pass on the trait to their daughters. This is the reason that, deep down, every woman wants to be submissive to a strong man, and will only feel totally safe and secure when she is."

"Bullshit! You are so full of shit!", she shouted. "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."

Same old PC bullshit. Men and women are clearly not the same. I stood up and barked, in my best parade ground voice, "Jessie, go get me coffee!"

The look on her face was priceless. Mouth open like a fish out of water, she stood there speechless (which was a bonus) for several seconds, before finally croaking out, "Fuck you!"

Sticking the knife in deeper, I continued, "Hah! Don't bullshit me. I noticed your hesitation. For a moment, for a second, you were torn. You wanted to obey me, and would have been somehow fulfilled if you had. Deep down, all women feel the need to be dominated by a man. It's in their nature."

Oh, Jessie. The tease, the wit, the snarky youth, finally had nothing to say. Bug-eyed, defeated (or disgusted), she muttered something under her breath, and went back to work. This verbal sparring was starting to be fun, almost a form of flirting, although I knew it would never go anywhere, it was invigorating, and I could almost feel the testosterone surging through my veins.

Still, I also wondered if I had maybe gone too far, said something so outside her comfort zone that it would drive her away, or worse, report me to the gender sensitivity coordinator. It wouldn't be the first time my facile tongue had gotten me in trouble, but a while later she was back, prattling on about football as if the earlier exchange had never happened. The only real difference I noticed in her behavior was a reluctance to look me in the eye. Something I said seemed to have resonated with her, had made her uncomfortable, so—perhaps unwisely—I decided to see if I could wind her up even tighter.

Jessie is a big Man U fan (of course). I prefer Arsenal, but Newcastle and MU were playing the following weekend, so of course I started arguing for Newcastle. "With Rooney gone, and Sir Alex a distant memory, Newcastle are really going to spank MU!" I taunted.

"You're crazy! There is no way Newcastle can beat Manchester. Its never gonna happen." she said, balling up her little fists like she would fight me if I disagreed.

"Want to put a wager on that, tweety bird?" I said. I knew Man U would easily beat the pathetic Newcastle, but I really didn't care about the money. It would be worth it to up the stakes on our little game, and watch her sweat all week, worrying that—however unlikely—the unthinkable might occur.

"Sure," she replied, "put your money where your mouth is. I could use twenty pounds."

"Okay," I said, "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 the following Saturday. In other words, be submissive. If you can do that all day, and still honestly disagree with my assertion by the end of the day, I'll give you the twenty anyway, to pay for your extra work."

I could see she was initially a little shocked by my suggestion, and then started calculating the odds. Being fresh out of school, her salary was low, so I'm sure she was thinking about the money, and I had (cleverly) sweetened the deal by essentially removing any risk she would not get it. After a momentary pause, still with her angry face, she said, "Okay, you're on!"

Later that Week

"Oh, oh, oh God, yes, yes! Put it in! Put it in!"

I was literally laughing as I watched Newcastle prepare to take a penalty. The game had been a bore draw until the last few minutes, when a Newcastle striker, with what appeared to be a blatant dive in the box, won an improbable penalty. Then, joy of joys, he put it in, and Newcastle won! I couldn't believe my luck. Although I was pretty sure Jessie would not actually go through with the bet, I would at least be able to tease her mercilessly for a while.

On Monday morning, as soon as she came in, I started in on her, and pretty soon the whole office (they knew about the bet, but not about the stakes) joined in the fun. All this was public, but later on, as we passed in the hall, I stopped her, leaned close, and whispered "Don't forget, you will be serving me this Saturday."

Jessie's jaw dropped, and anxiously she said, "You're not really going to make me go though with that are you? I'll pay you the twenty."

"A bet is a bet," I replied, "and I want you there at 8:00, ready to serve." This was simply delicious, and I'm sure I was grinning like a fool as I added smugly, "And wear a dress. I want you to look ladylike, for once."

Jessie wandered off mumbling, and miracle of miracles, had nothing to say the rest of the day, and little to say the rest of the week. Although I missed (a little) our verbal jousting, I also enjoyed the blissful peace. I had plenty of time to imagine how this would play out on Saturday, in the unlikely event she actually turned up, and I have to admit that my fantasies were a lot more graphic than reality was likely to be. But a boy can dream...

The week passed slowly, but finally Saturday came, and I was in the office early, ready to play the teasing game in earnest if she came to work, but failed to follow though on the terms of the bet. I waited a while, but she didn't turn up, so I focused on work. Although I was disappointed, I wasn't surprised, and at least I would have the moral high ground in our arguments for a few weeks.

Around 8:45, long after I'd given her up, I heard the office door open, and there she was. And, by God, she was wearing a dress! I couldn't believe it, but I guess she had more balls than I anticipated. I was a little unnerved, and wondered how this charade would play out now, but decided to get into the spirit of the thing right off.

"There you are," I said sternly, "and you're late." And then, approvingly, "But at least you wore the dress. Very nice. Very feminine."

"Fuck you!" she replied, "I didn't wear it for you, I just felt like it."

Although I was acting confident, like an alpha male, I was a bit uncertain. Despite my lurid fantasies, I had never really expected Jessie to go through with the terms of the terms of the bet, and her actions now were almost completely unanticipated. I wasn't sure of what she was really up to, or how she figured she could turn this against me, but knew she was very clever (if inexperienced), and I didn't doubt she had some plan to turn this against me. But, for lack of any better idea, I decided to play out the game, and see what she had in store.

"Okay. Whatever. Now bring me coffee."

"Asshole," she muttered, and turned and left.

Well, I thought, that didn't last long, but a few minutes later she was back, slamming down a coffee on my desk, so that some slopped over the side, splashing some important papers. I was surprised, but also a little pissed off at the stains. "Jessie," I said, angrily, "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. Now!"

"Fuck you!" she said, but then asked, "You are not really going to make me do that are you?"

"On your knees," I ordered. She looked a me in silence, and I could see an internal struggle play out on her face.

Then, after ten seconds or so, she picked up the cup, knelt, and said in her most sarcastic tone, "Your coffee, oh lord and master."

"Better. Much better. But, no need to call me master. Sir is fine," I replied. She got up and left, and I sat there, trying to figure out what this all meant. Was she playing a game? Was she actually flirting? How far would she go? Whatever it was, seeing her kneeling before me, her ample cleavage exposed, was damn sexy, and had given me a rigid, almost painful, hard-on, that luckily was concealed by my desk.

I couldn't work. I just kept playing that scene over in my head, my cock hard and leaking. Finally, I had to go to the men's room for some relief. When I got back to my desk, I still couldn't concentrate on work, so I called Jessie for another coffee, and this time she was a little less sarcastic, and knelt without prompting beyond a gesture with my hand. I repeated this several more times that morning, enjoying myself, even though the coffee, and other stimulation, necessitated several more trips to the loo for relief. Each time I called, she was more submissive that the last; until finally, shoulders rolled forward and eyes downcast, she would kneel without prompting, and humbly say, "Your coffee, sir."

She was definitely into playing this game, and I became more and more convinced that this would actually end in sex. As midday approached, I couldn't stand the tension and suspense, and decided to bring the game to a head. Either it was a long, elaborate tease, that she would torment me with in the weeks ahead (most likely), or she was ready to go all the way. One way or another, I had to know.

"Jessie, come here!" I shouted from my office, where I was seated on the sofa, reading (or trying to read) a program report. I could see her get up from her desk and walk towards me, looking a little unsteady on her feet, her eyes unfocused. Although she was playing a game, she looked deep into it.

"Yes?" she asked, in a soft voice.

"Yes, sir," I demanded, pushing her to continue the fantasy of our master/servant relationship.

"Yes, sir," she responded, without looking up at my eyes.

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

"Why?" she asked, "Do you want more coffee"?

"Don't ask questions, Jessie. This is just part of the bet. You have to do as you are told," I said, then sternly ordered, "Come now, and kneel!" And, after a moment's hesitation, she did! Pushing it to the limit, I said, "Now, down on your hands," and she dropped immediately. Wow! Had she had not been looking down, she would have seen absolute shock on my face.

There she was before me, on hands and knees, shaking a little. Was it fear? Anticipation? Whatever it was, I knew at that moment that she was ready for sex, that she wanted it. I couldn't help it. I reached out and laid my hand on that perfect ass, barely covered by a thin cotton dress. So thin, I would see the elastic of her knickers outlined in the soft cotton.

"What are you doing!" she said, in a panicked voice, keeping in character as we got closer to the act. I felt I had to keep in character as well, even though I was almost overwhelmed with lust. I started to lightly massage her back and leg.

"Jessie," I said, "don't be nervous. This is just the final part of the test. I just wanted to demonstrate that deep down, like all women, you want to be controlled. Think about it, you are on your knees for me, and if you are honest with yourself, deep down you like it. Admit it."

"No!" she said. "No. This is wrong." And she started to get up. But by then I knew it was just a game, she was just pretending, and I put my other hand on her upper back to hold her down.

"Stay! Just five more minutes," I said. "If after that you still disagree, we will be finished. I'll admit you are right, and you will get the twenty pounds. You want the money, don't you?"

She stopped pushing, and said, "Five minutes. That's all, then the money".

I continued my slow massage, kneading her calf and then thigh, and I could feel the tension draining out of her. I was lucky that her head was past my knee, because if she had been able to see my lap, the massive and painful hard-on trapped in my trousers would have been unmistakable. I wasn't sure how long I could keep up this charade.

"That's good, Jessie. Enjoy it. That's right. The more I massage you, the more I control you, the better you feel, right?" And with that I couldn't stand it anymore, I couldn't pretend any more, and started working my hand up her leg, and under her dress. I had to have her, now!

"Stop! Stop!" Jessie yelled, as my hand reached her knickers. "Stop it!" she yelled again, and tried to get up. "Don't, please don't!"

But there was no stopping now. It may have started as a game, but I was now living the part for real. The primal male had emerged, and I wasn't playing anymore. I wanted to control her, and got a better grip on her neck, then growled, "Jessie, your panties are wet, very wet. Words don't matter. Your body is telling me, and telling you if you will listen, that deep down you want this. You want to serve me, to obey me. You need to be controlled by a man to feel like a real woman. And now I've won my bet!" And I laughed.

Then she really started fighting me, screaming, "Fuck you, you asshole! You fucker! I'll.. I'll.. unnghhh..." Not thinking, running purely on some animal instinct, I had grabbed her hair to hold her down, and shoved a finger under her underpants and into her sopping pussy. I held her there, trapped between my hands, and experienced an immense feeling of power.

"Noooo... please, no!" she wailed, but I couldn't stop. I pushed her head over on to the sofa, and got down on the floor behind her, and pulled down her knickers. She continued to pretend, to object and struggle, and I grew rougher, knowing she wanted it this way, and realizing that at that point, so did I. I unzipped my trousers, and pulled them down, letting my engorged member spring free. It was some relief, but still so hard it was painful.

"You want this, you bitch! You have wanted it wanted it for a long time." I grunted, slipping my dick between her thighs, and rubbing across her wet and slippery mound. Even that was a tight fit, as her legs were constrained by the knickers now around her knees.

"Stop, stop, don't do this," she pleaded.

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

"Please John, don't do it! Please, please, oh no, please! I won't tell anyone, please no..." she begged, keeping in character long after I had given up on the game. What I was now was the real me, but me beyond rational control, me after months of pent up desire, and hours of bursting balls. It was me, but I was anything but normal.

"Feel that baby. You know you want it. Say you want it. Say you want my fat cock in your pussy. Say it!" I demanded, jerking back on her ponytail.

"Fuck you, you bastard!" she screamed.

I ignored her acting, her game, her trying to drag this out. It had gone on long enough. I needed this now. I lined up with her pussy, and started to push in. It was wet, but my God, it was tight. I could tell she wasn't a virgin, but she certainly hadn't had much experience.

"Ooohhh...nooooo...uhh, uhh, please...stop..." she gurgled, as she tried to squirm away.

Now she sounded serious, and as tight as she was, I didn't doubt she was in real pain, but I couldn't stop if I wanted to. A part of me was appalled, but that part seemed to shrink farther into the background. The older, more primitive part of my brain was in full control. As I continued to press, and she to moan, I felt her trying to spread her legs, and then heard here knickers rip. Shredded. Immediately I gained another inch, but it was still slow going.

"Unnnngh....mmmmph...ooohhh..." she moaned; the sound of her discomfort driving me wild.

"That's it baby. God, you are so tight! So wet! Come on, take my meat in your little pussy."

"Please... oh god... no... please, it hurts... oohhh. Stop... please, stop... ohh god omnagh ohh."

Then Jessie started crying, really sobbing, her body shaking. It was then, I think, that my rational brain finally started to suspect she hadn't been playing a game. She hadn't wanted this. She had actually been sincere in trying to make good on an unwise bet, and I had misunderstood everything. And now I was forcing her; really, I was raping her!

But I kept pushing. The lizard brain was in the driver's seat; the ancient imperative to breed, to reproduce, in full control. I couldn't stop, I didn't want to stop, and I didn't stop until I was finally all the way in, my pubic hair pressed to hers. And it felt good. So good. Better than anything I had ever experienced.

"Oh so good baby, so good, so tight, so sweet," I hissed. "You took it all baby, you did it. Now relax baby, just relax."

I drew back, and then slowly pushed in again. In and out, back and forth, I started getting a rhythm, and as I did her sobs and shaking subsided, replaced by little moans and gasps. Within a few minutes Jessie seemed to give up, to stop fighting, and even to begin to follow my rhythm.

"That's it baby, now you feel it." I let go of her neck then—there was no longer any need to hold her down—and shifted my hands to her hips, increasing my pace, faster and faster until I was slamming into her, the sharp slap of my thighs against her ass a counterpoint to her low and continuous grunting and moaning.