Boss Lady

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Loser gets to serve a superior Woman.
4.9k words
4.25
43.4k
27

Part 1 of the 3 part series

Updated 09/22/2022
Created 09/10/2014
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It wasn't the first time I'd stood up to a woman and been knocked onto my ass. All I could think of at the time was that here was a pushy bitch riding roughshod on my plans; plans with much time and effort invested in them. She had come sashaying into my office while I was planning the day's schedule with my assistant, Bernice.

"Tim, I won't beat around the bush." she said. "I've had doubts about your strategy with the Demerest account all along. I've just talked to Grant, and he agrees that we should rethink it all. I wanted to tell you myself."

I stared aghast at her as she stood there surveying the room; looking at it as though she were redecorating it in her mind.

"Bernice, will you excuse us, please." I said icily.

'The fucking nerve of her!', I thought, waiting for the door to close.

"You went over my head." I began, my fists clenched on the top of my desk. "I thought we were working as a team - all of us. I thought this was a team effort!"

Jenna sighed and cocked her head to one side.

"I don't know, Tim. I mean, we have talked, haven't we? You know how I feel about it. Bob Demerest wants a better return, and your so-called diversification strategy is getting him a case of financial anemia."

"Rubbish! He's getting a solid nine percent over time. He's happy. And, frankly, I'm not concerned about whether you are."

"Now, now, Tim. Reality can be unpleasant, but you need to face it. I'm running the account now. And though you may not care about my happiness, just so you know, I'm really quite pleased at this turn of events."

Jenna walked past me to the window, her hips moving carelessly under her tight skirt.

I hated her guts, but I also loved watching her move. Leaning against the window frame, she surveyed the street below.

I swiveled my chair to face her.

"You fucking whore." I seethed, my voice trembling with rage and impotence.

"Oh, I'm a whore. Is that it? I have some innovative ideas, ideas that Clark likes, I should add, and suddenly I'm a whore? Get real. This game is called hardball, my dear."

Her nonchalance angered me further. She still had her back to me as her eyes moved over the scenery. I took in her tall frame, her no-nonsense short haircut. I tried not to feel the hunger I normally felt when I was checking her out, but there it was. God, she was hot. She was of a slight, elegant build from her small waist up. On the downside, that waist gave way to gorgeously rounded hips and ass. Watching it all shift and move when she walked was one of the great pleasures of any work day. But for now, it infuriated me that I could not put my lust aside. Here I was being screwed by this ballcutter, and inside I was drooling.

"Looks like storm clouds on the way." she noted casually. "So, look," she said, turning towards me and leaning against the sill, "I'll forget your impudence this time. If it happens again, I'm going to have a sit-down with the big guy. I don't think he'd approve. You need to learn to take some knocks without taking it personally. I mean, you'll last longer. What do you say?"

I wanted to stand up to confront her, but I was beginning to have an erection.

"I'm going to have a talk with Grant myself. I'm not going to be walked on." I said emphatically.

"I'm sure he wants to talk to you as well." Jenna replied, smiling mischievously.

"What have you been saying about me?" I demanded, and got up from my chair.

"Oh, Clark likes to bounce things off of me. we talk about this and that."

I'd like to bounce an ashtray off your skull, you cunt! I fumed inwardly. But even as these words formed in my mind, I could not help wondering just what her cunt smelled like. There was always a deliciously warm, female fragrance exuding from Jenna, and I often fantasized about discovering its hidden sources - her soft curves, dark orifices.

"Well, we talked about you this morning. Anyway, he'll tell you more about the Demerest changes. You could go up to his office now. I'm pretty sure he's free." she said, looking me straight in the eye.

She looked at her watch. "I should really get going. By the way, that's a nice suit. Fits kind of funny in the front, though." she said, suppressing a smile.

She strode to the door and damned if my eyes didn't follow her as she left. Then I looked down and saw that the contour of my semi-erect penis was showing. I returned to my desk and, with my head in my hands, broke down. Thank God she had left before then. A twisted mix of emotions - indignity, rage, and long-repressed sexual longing welled up and battled for dominance. But, through sheer will, I collected myself, and my thoughts turned to reprisal.

I walked down the carpeted hallway and stopped at Vivian's desk.

"Grant's expecting me." I said. My hands were clammy and my jaw was clenching with anxiety.

"Go right in, Mr Byron." she said, and I pushed open the heavy oak door.

"Tim! Have a seat. Did Jenna tell you about the tweeks to the Demerest account? We want to run them past you first, of course. Have a drink? It's four o'clock. I'm having one." and, with that, Simon poured scotch from a decanter.

"Sure. I'll have one with you." I said. I needed it, really, to calm myself. I sank into one of the leather armchairs that faced the desk.

"Ice?"

"Just a couple of pieces."

Grant came forward with the drinks and sat in the chair beside me.

"Bob Demerest has been hinting at a fatter bottom line ."Grant said as he settled in, swirling his drink.

"You've done good work with him, Timothy. No question. Solid work. But now he's looking for capital. He's investing in condos in Florida. In Naples. It's a good move, and I told him so. He wants to crank up his returns here, though. I don't have to remind you that Ed Ralston is vying for his business, and I'm not about to just give it up."

I heard the door open, and I stiffened. Clark rose from his seat.

"Jen. Come on in. Just talking to Tim about the account. You don't like scotch, as I recall. Bourbon?"

Jenna nestled into the remaining chair and crossed her legs.

""A mineral water would be nice. A good vodka would be nice, too, but you don't stock it." she said. Grant brought a pelligrino from the small fridge.

"that can be fixed. what's your pleasure?"

"Grey Goose ."

"Consider it done. Come by tomorrow, and we'll drink to it. Now," Grant continued, leaning on the edge of his desk and looking from one to the other of us. "Let's talk Demerest. Jen, tell Tim what you have in mind."

I looked over to the whore and tried my best to convey my loathing for her. She held my gaze for a second, recrossed her legs, and began.

"Putting him more heavily into healthcare - say, moving three mil into Genentech...it's going places. I've done the research. He should have the money he's looking for in the first quarter of next year. That, by the way, is when he wants it."

"It's good analysis, Timothy. I had Randy go over it. What do you think.?" Grant said, turning to me.

"Sounds to me like it's already done. If that's what you want..."

"I'd like it if we were all on the same page here, Tim. You're sounding a bit defensive." Grant said. He seemed irritated, and I took his words, especially in the presence of Princess Bitch, as a slap in the face. He was dressing me down, and I knew she was loving every bit of it.

"I can send over the data, Tim." Jenna said, sounding very sure of herself.

"Sure. Sure." I said, not sure of what I was saying. I looked at her, but my gaze dropped. What the hell. I was whipped, and I was whipped by her. I felt emotion rise up in me, and thought I might be dangerously close to losing it as I had in my office earlier. Clark seemed to notice.

"You all right, Tim?"

"It's nothing." I said. "Indigestion, I think."

I bit my tongue in an effort to steel myself. Jenna was looking at me as she sipped her water.

'That's right, twat. You won', I thought, pursing my lips tightly so they wouldn't tremble. She continued looking at me while Clark was on the phone with Randy, our chief analyst. Her steady gaze discomforted me, and I could feel my insides squirming.

Grant hung up the phone.

"Well, I guess that's it. Tim, why don't you review Jenna's data, and we can meet again tomorrow. I'm looking forward to your weighing in on this."

We both got up to go, and I was at the door.

"Jenna, stick around for a minute, will you?" Grant said.

Jenna caught my eye as I opened the door. She answered Grant, but she was looking - and smiling - straight at me.

"Sure, Grant." she said, and turned her back to me.

I fumed my way back to my office. Jesus, I felt like the floor had disappeared from under me. Suddenly, my status in the company seemed uncertain, at the very least. Oh, I'd keep my position, but I could see clearly that I was no longer Grant's go-to guy for the larger accounts.

'All because of that filthy bitch!' I muttered to myself as I made my way down the hall.

The next morning there was a note from Grant in my inbox.

Morning, Tim.

Jenna had the idea of all of us meeting at her apartment after work. She's ordering some catered hors' d'ouervres. We'll get a few bottles of red, and mull things over. Her place at seven.

Regards,

Grant

Sure, why not? As if I were important to this so-called meeting. Hey, Grant. Why don't I just stay outside and wax all of your cars while you have your talk. Fuck! Well, I couldn't not go. But the idea of accepting her hospitality really galled me. What could I do, though?

Later, I thought of something. I'd bring the wine. I'd offer to do it. Then, I would bring bottles of the finest premier cru bourdeaux I could get my hands on. I would steal the show!

I left work at five, and went directly to to Marcel's, a purveyor of fine wines. I came away with six bottles of Chateau Margaux, '95. They wrapped them in colored tissue paper, and boxed them up very nicely.

When I arrived at Jenna's place, I placed the box on the coffee table in the great room. Everyone else had already got there. Jenna removed a bottle and examined it appreciatively.

Hey. Good stuff, Tim. The '93 was a super vintage. Not sure how this one compares, though.Can't wait to find out! Where'd you get it?"

"At Marcel's."

"Oh? He has the '93. I'll give him a talking-to next time I'm in there."

So, I had fucked up again, was that it? And been taken for a sap by a crafty wine merchant to boot. It seemed this woman took real pleasure in defeating me. I felt like a clumsy, punch-drunk fool in the ring with a master boxer. Every time I turned around, I caught a stinging jab right in the face.

The meeting was done within two hours. Who can say if anything got done. Grant pulled a soliloquey out of somewhere, going on about a new, higher level of energy he was hoping we'd all adopt (a la Queen Jenna, no doubt).

I had my share of the wine. It tasted fine to me. But then, I'm just some bumbling oaf. What do I know? Well, by the end of the soiree, I knew that Jenna was spearheading the Demerest file. Our most prestigious. What a joyous occasion. There were even a few seconds of congratulatory applause. I don't know why I didn't just say: Excuse me, I'm going into the next room to hang myself.

People started clearing out. I was finishing a brandy that Jenna had been pouring around. I vowed to stay behind and offer some conciliatory words to the cunt. It wouldn't be easy, but I had to think about keeping some respectable position in the pecking order, even if it involved riding on missy's coattails.

I started picking up glasses from around the room.

"Thanks, Tim." Jenna said as she returned from seeing the others off. "Put them by the sink, will you?"

"Okay," I said. "Thought you might like some help."

"So it would seem". she said in a quizzical tone.

"I have to tell you, Jenna, you're doing really good work. I just didn't appreciate your efforts till now."

There. I'd said it. I'd let her wipe her feet on me like a cowed, spineless piece of shit! 'Why don't you wipe your ass on my face, while you're at it!' I sputtered inwardly.

"Well, if that isn't a one-eighty! You weren't feeling like this yesterday. Makes me wonder if your being sincere." she said, casting a critical eye at me. So she wasn't going to graciously accept my praise. Maybe I should grovel at her feet.

"I'm just trying to pay you a compliment, Jenna." I said, sounding innocent.

"It just seemed a bit odd, is all. It's nice to hear praise, but unexpected when it's coming from someone who clearly loathes you."

"Oh, well,maybe I can stick around a bit longer so you can humiliate me some more, you, you..."

"Ah! Here's the real Tim." she said, putting down the plates she'd collected and facing me. "Maybe I will let you do just that, little man. You really are cut out for it, aren't you?" she said, and she laughed.

"I just want to make peace, is all." I said, hanging my head.

"And what word was on the tip of your tongue just then? Huh?! 'You, you', what?! Bitch? Cunt? Speak up, Timmy!"

I looked into her eyes as tears began to form in mine. Fool! Control yourself! But she saw. She saw my weakness.

"I don't know what else to say, except that you are obviously a coward". Jenna taunted, standing there, hands on hips. "A sniveling one at that. Jeez. You are one sad sack of shit, you know that?"

"Cunt." I muttered.

"What's that, Tim? I didn't quite get that."

"You stinking, lousy cunt!" I growled, and felt my face turning red from the slew of emotions that churned in me.

Jenna walked swiftly up to me and slapped me hard across my face. The sound of it astounded me. My face stung and my ear rang from the blow.

"Not allowed, Tim!" she said forcefully. "Think what you want, but you show me respect, you understand?"

I stood there, dirty glasses in my hands and I wept.

"Keep busy, Timmy boy. Get those dishes into the dishwasher, then do the carpet. The vacuum is in the closet by the front door." With that, she left the room. I carried the glasses into the kitchen, my vision obscure by the tears that now flowed freely. I sobbed openly, feeling as though a floodgate had creaked open in me. I methodically went about my task. Slapped silly by a willful, pushy bitch. Isn't that lovely.

I slowly got command of my feelings. I was vacuuming the carpet when the machine just stopped. I turned and saw Jenna tossing aside the cord she'd unplugged. She was wearing the top she had on all evening, and panties.

"Come here." she said as she eased herself onto the sofa. I began winding up the cord, my hands trembling.

"Leave it. Just get over here." Jenna said, snapping her fingers. "Waiter, how about some service, here? You do look like a waiter, doing all this lovely cleanup, Timmy. You don't mind if I call you Timmy, do you?"

This was simply unreal. All Jenna's beautiful female flesh that I had long worshipped in my dreams sat relaxed and naked before me. I knew that she was on a beach volleyball team and, so, was not surprised to see the milky-white of her lower belly give way to the golden hue of her legs and torso. Jenna's long legs were crossed at the knees, but when I approached, she uncrossed them, and allowed them to fall to the side. I couldn't keep my eyes off of her thighs. They were gorgeous.

"Kneel down. You're making me crane my neck." Jenna snipped. I lowered onto my knees, and the warmth and fragrance of her body wafted towards me. I inhaled it eagerly and raised my eyes to meet hers. It was then I realized that I was afraid of Jenna - afraid of how she could easily reveal me for what I am; not the phony persona I present to the world. Truly, if aliens studied our culture, they'd wonder why women like Jenna didn't have balls, and why weaklings like myself did.

"Look at me." Jenna said in a surprisingly soft voice.

"I didn't realize you were such a crybaby, Tim. What seems to be the problem?" she said, resting her hands on the tops of her thighs.

"I don't know. It just came over me." I said as I struggled to meet her gaze.

"Are you afraid of me?"

"A little, I suppose." I said, feeling ashamed of fearing my tormentor. No balls, Timmy. You might as well own up to it.

"Afraid how? What is it about me that makes you afraid?"

"I don't know." I said.

She leaned forward. "I want actual answers to my questions, Tim. Is that Understood?"

"I'm sorry." I said as a surge of desire took hold of me. How long could I remain this close to her gorgeous body without cracking up?

"Tim, is it sexual? Because maybe you're afraid of how much you want to serve me. I mean, lets face it, that is your style, I'm wagering. Servitude. I'd say you are a timid and submissive man. Agreed?"

I nodded my assent.

"Yes, and that's just as well, because I don't think any woman knowing your ugly thoughts regarding womanhood will let you anywhere near her bed." she said in a cold and level voice. "But you might be handy to have around the house."

Jenna was savoring her power, her victory over me. And I just stayed there on my knees taking it.

I shifted my weight from one knee to the other. "I'd like to try." I said in barely a whisper.

"Pardon me? I didn't hear you, Timmy."

"I think I could be a good helper." I said, and looked up to see her smiling.

"Fantastic, Tim! You know, I really enjoy my dominance over you in the office, but this... this will be something special. I imagined it, you know. Having a sexually perverted, spineless, male ass - that would be you - entirely under my thumb in private. "You!" Jenna laughed, and there was an excited glow on her face.

"Why we'll have to reshape you, I believe, Mr Tim-Tim!" she said gleefully.

"Yes, please!" I blurted out, and my voice quavered. "Just tell me what to do...Ma'am, and I will do it."

I had never felt so degraded and yet so ecstatically liberated until that moment. I had declared a deep and secret wish. A shameful one, really, since I could no longer see myself as a whole man; a self-respecting man. But one, however, whose destiny was suddenly set ablaze.

"Well put, Tim! And in just a few simple words. The very words I want to hear from a man. Here, kneel on this." she said, tossing a pillow at me.

"Before you get too comfy, run to the kitchen and make me a screwdriver. Let's go! Pronto!"

The words sent a thrill through me. Orders. Orders for me from a strong, no-nonsense woman. I would do my very best to impress her! Don't blow it, Tim!

I stepped briskly to the kitchen and scanned the room for a bottle of vodka. I didn't see one, so I rounded up the ice and juice. Now I was beginning to get anxious. Where the fuck was this vodka? I wasn't about to go before her and say I didn't have her drink!

I opened and closed cabinets - there must have been twenty of them! - as quietly as I could.

"Tim! Tim, come out here." Jenna called.

I dashed from the kitchen, nervously twisting a dishtowel in my hands.

"Stand in front of me." she directed, and I obeyed.

"Umm. What are you doing out there? Where's my drink?"

"Im sorry, Ma'am. Sorry. I searched everywhere for the vodka, but I haven't found it yet. I'm sorry, Ma'am." I said, the words tripping over each other.

"So, let's see if I've got this right. You decided that I could wait for my drink while you run all over the kitchen?"

Jenna rose from the sofa and walked up to me.

"Is that it, Tim?"

I know that my mouth was opening when the flat of her hand came like lightning across my face. Then the other hand.

"Give me that thing, stupid". Jenna said, yanking the dishtowel from my hands.

"Look at me, Tim. Do I look like I'm fooling?" Jenna said, right in my face.

"Next time you don't know something, and you need that something to please me, you come to me and you politely ask. I don't have time for you to take care of your ego. Is this sinking in, Timothy?" she said, stepping back, and looking stern, indeed.

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