When All is Lost, Fuck Your Boss

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A company down in flames, a boss down on him.
2.8k words
4.51
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iwiwt
iwiwt
213 Followers

"We're fucked," I said.

We really were. Math never lies.

"Jesus Christ," said the old cougar I worked for, leaning over my shoulder in her office, "I'd fucking say so."

All the lines of the budgetary spreadsheet that should have been green were red. Most of the important numbers ran in the negatives. The proof was right there, in rows and rows of uncaring data. There would be no recovering from this. The pivot tables said so, clear as day.

It was past midnight by then, and I was exhausted. I'd been trying to force things to make sense, to command some order over this disaster for hours. There was nothing for it; come Monday morning, our Q3 financial report would go public, and the real shit show would begin. I pushed my glasses to my forehead and buried my face in my hands, afraid to let Michelle see me cry. I heard her step around me, to her own side of the desk. A drawer opened. Glass hit the table.

"How did this happen?" I wondered aloud into my palms, too tired to consider the possibilities again.

"Well frankly," she began as I heard a bottle uncork with a cracking POP, "as my little bean counter extraordinaire, I had hoped you might tell me." Something smoky and distilled filled one glass, and then another. "Come on kid, drink up."

I uncovered my face, peering down at the heavy rocks glass full of dark brown liquor she'd shoved in front of me. Hers was almost empty already, and she drained it in one long gulp while staring forlornly out the window.

"You're drinking? Now?!" I asked incredulously, "at a time like this? Hang on, you can't smoke in here!"

My protest went unheeded as she sparked the cigarette anyway, blowing a long stream of thin blue smoke into the air.

"Listen," she said in her dry rasp, "you said it yourself, we're fucked. What are they gonna do, fire us?" She barked a harsh laugh and pulled another long drag. She had a point; getting fired was the least of our worries. As a publicly traded company, we'd be lucky to avoid prison for more than a dozen of the sums on this balance sheet alone.

"Shit," I muttered, snatching up the offered glass and choking down the tepid whiskey. Michelle watched me pull a face with bemused seriousness, filling her glass anew and sliding the bottle over to me.

"I'll pour your first but you'll have to be a big boy past that," she said, tearing the lanyard with her ID over her head and shaking her mane of greying brown hair out. She'd let it grow out after overhearing the receptionists affectionately calling her Ms. Clairol last year. I couldn't believe the old girl hadn't just fired them right then and there. She'd canned a dozen of my peers for less. Her alternate nickname, The Maneater, was well-earned, if painfully unoriginal. She'd never taken a bite out of me though, much to my relief; I think she had a soft spot for me.

"Am I going to jail for this?" I asked timidly.

"What?" She said, snapping back from some dejected reverie, "Oh fuck, no, probably not. You'll be fine."

"Really?" I asked, "because this is really bad."

"Oh it's worse than that," she offered as she leaned back in the heavy leather executive chair, doing little for my confidence, "but little guys like you always make out alright in these things." She kicked off her heels and swung her feet up on the desktop.

"How do you know?"

"Well," she said, staring at the lit smoke burning down between her forefingers, "I was a clerk at Enron once upon a time, and things turned out alright for me, eh?"

I neglected to point out that things were not turning out alright. I hammered another finger of the harsh whiskey down my throat, managing a poorer show of keeping a straight face as I did so.

"Jesus kid," she said, again reminding me of the twenty or more years between us, "you're terrible at this." She reached over for the bottle, skipping the glass this time to take a hearty swig.

"Drinking and balance sheets, two things to avoid in the future," I offered miserably, wiping my chin with the back of my hand. She barked a blunt, hacking cough of laughter.

"Was that a joke? That's pretty good," she chuckled, ashing her spent cigarette in a well of paperclips on the desktop.

"Yeah well, I'm glad there's hope for me yet, even if I'm destined for the circus with all my hilarious jokes after this." She chuckled again. It wasn't unflattering to hear her laugh.

"Well then," she said, slapping her thigh through the stretched black fabric of her pencil skirt, "what do you say, huh?"

"Sorry?"

"Are we fuckin' or not?" Not evidently in the mood to wait for a reply, she swung her legs off the desk and rose to her feet, working at the buttons of her already low-cut blouse as she towered over me. I was more than a little lost.

"But, aren't you...wait, what? Aren't you married?" I stammered, watching her implacable progress as she continued to disrobe, untucking the shimmery top from the hem of her skirt and dropping it to the floor. She stood, hands on her hips, expensive looking black bra working to contain her heavy freckled tits. In a word, she was 'sturdy'. In two words, she was 'very fuckable'.

"Oh who gives a fuck about that sad sack of shit," she insisted, waving a hand to blow the notion of committed decency away like it was a pesky mosquito, "if he's allowed the fuck his secretary then I'm gonna get mine." She regarded me as though I was a gas station sandwich; not great, but it'll do when you're hungry. "Well," she insisted, "are we doing this or not? I don't mind pouring you a drink but I'm not taking your pants off for you. This isn't fucking prom night."

Not willing, and less likely able, to deny her, I scrambled into action, trying to fumbled at my belt buckle while still seated in the chair. Satisfied that her meal wasn't going to run out on her, or go cold, she treated me to a wry grin and tugged at the side zipper of her skirt while I piteously scrambled at my fly.

I stood, at last, and let my slacks drop to my ankles along with my briefs, letting the cool office air tickle my bare ass as I stood bottomless before her, unsure what to do with my hands. She wriggled her wide hips and exceptionally ample ass out of the skirt, kicking free of it too.

"Lose the shirt buckwheat, let me see what we're working with here," she demanded. Wanting to impress, I tried and failed to tear the button-up open, succeeding only in popping the top three buttons and otherwise ruining a good shirt. She laughed at the wimpy display while I scrambled to undo the rest more traditionally. The flaps of the long shirt opened as I shrugged it off, letting her feast her eyes on her midnight snack.

"Okay!" she announced, "not half fucking bad, kid! We can work with that!" The look of appreciation seemed genuine enough, and my heart and cock swelled at the compliment. "I hope to god you know what to do with that thing." She said, unceremoniously unhooking her bra and rolling her shoulders forward to let the straps fall away from her as she peeled it off. God, but they looked heavy. And soft. She tucked her chin to her chest as she looked down at them with me, swiping away some unseen crumb or hair as she regarded them.

"Well, you like 'em?" she asked.

"Hell yes," I said breathily, drawing another short laugh from her.

"Come and give them a squeeze then, huh?"

I did as I was bade, stepping forward with arms outstretched, running my hands up and over them, relishing their impossibly soft heft. She clapped a hand over mine in a clawing grip abruptly.

"That's not a fucking squeeze," she said in mock anger, "this is!" Her rough clutch was a crude demonstration, but she was still my boss, and I'd never deny her.

"There you go! Like that!" she growled, reaching down to tug at my growing cock while I gave her heavenly tits a proper grope. Her nipples were great gumdrops and I dared a pinch. "Ah!" she exclaimed, "that a boy! Do it again!" I did as I was told, rolling each between my forefinger and thumb tightly. "What do you think, you gonna give me what I want, huh?" I agreed with a hearty nod.

She let go of my dick and turned to bend over the desk, waving her fat bottom delectably in the air for me; the dainty thong I never thought to find on a woman her age was all but devoured by the cleft of her jiggling, cratered ass. I stepped forward and grabbed at the thin fabric banding across the tiger stripes of her hips, ready to tug them off.

"Now hang on one motherfuckin' second," she said, turning back to face me with a devilish grin as she swatted my hands away, "must you young things always be so greedy?" She dropped to her knees before me, gripping my upright cock firmly, carelessly spitting at the underside of it. "I gotta get mine here too you know?"

Before I could protest, she shoved the thing into her mouth without so much as a warning. Eschewing the tendencies of younger women, who think that the only thing men want is a gagging deepthroat, Michelle's tongue was a hurricane of motion against my taut head, battering the few inches she'd taken into her mouth mercilessly. The effect was divine, as was the auditory assault of her slobbery affections while she hummed happily on her snack. She tore it back from between the suctioning vacuum of her lips with a loud smack, smiling up at me from the floor.

"That's a hell of a cock you've got yourself," she praised, rubbing me in a strong grip, "I bet the girls love you, eh?"

"I do okay," I said, still reeling from the ferocity of her brief blowjob.

"I bet you fuckin' do," she laughed, rising back to her feet and turning back to lean over the desk again. "Now you can take them off," she said over her shoulder.

Obliging, I tugged the scrap of fabric away, letting her kick it aside as she braced her feet apart, chest pressed to the desk that she reached across to grip the far edge.

I lined up on her, squatting slightly to account for the height difference between us. She was wet to my touch as I pressed myself against her slit, and at least halfway furry if the scratching sensation on my cock was anything to go by. As big as I am, slipping into her was easy like a Sunday morning, and the familiar feeling of warm security enveloped me snugly. She let out a guttural grunt, which suited her character to a tee, and I drew back to begin pummeling her.

Or so I thought. Giving her everything I had, and more, the feral groans and animalistic huffs were at odds with her apparent dissatisfaction.

"Oh, unphh, come on big boy, hmph," she grunted between strokes as I rode her roughly, holding fast to her hips in a white knuckle grip, "I'm not gonna, oof, break you know. Ah! Fuck me now, come on! Gah! Fuck me!"

I doubt she'd ever been called fragile before, but I redoubled my efforts, damning the cramping burn in my thighs and abs as I slammed myself against the fleshy mountain of ass flesh she pointed my way, determined not to let her down. My breaths came in ragged gulps as I listened for any sign of approval from her.

"There, ugh, we go! Hmph! That's more, unph, like it!" I reveled in her praise, catching a second wind, "Smack my ass! Ahh! Come on!"

Without a second thought, I cracked my boss across her ass with thundering abandon.

"FUCK!" she shouted, "Yes! Again!"

I slapped with all I could, easily landing a cracking blow across my unmissable target. The rippling mounds reddened with angry red welts almost immediately.

"More!" she demanded, "Fucking slap my ass while you rail me!"

The snappy reports of my body slapping against her, in time with my violent efforts to abuse her tender ass cheeks, made for a riotous cacophony. She wailed with glee as I flailed at her again and again, loudly announcing that she was cumming as her knees buckled monetarily.

Disappointed to have slipped out of her as she fought to compose herself through the orgasm, she straightened her legs and worked her hips up and down against me, grinding my cock between her cheeks like a human sausage bun. The wet smear of her slimy coating painted shiny streaks along the cleft of her rump in a pleasing way, but I needed more of her.

"Roll over," I commanded, and she squealed with glee as she clambered onto the heavy desktop, rolling onto her back and clutching her knees open for me in a brazen display.

I wasted not a moment, and drove myself back into her quickly, reveling in the tight-cropped forest of moderately tamed hair she sported. The lip biting stare that she treated me to drove me wild; I was insatiably hungry for her, and held the tops of her hips as I carried on fucking her wet hole greedily. The little pouch of tummy fat, tattooed with an uncharacteristically dainty butterfly, wiggled and jiggled along as I defiled her right there on the desk of her office.

"Fuck me, yes! Just like that! God yes, fuck me harder! Come on, that's it! Give me that big fucking cock, right up inside me. God, you feel so fucking good right now!" The barrage of compliments tipped me off the ledge of reason and I ravaged her beyond reason or care. Letting go of one knee, she ground the fingers of one hand to her clit while I pistoned in and out of her, rubbing herself into oblivion as she came freely on my dick.

"FUCK!" She shouted, torso quivering with the tremors of her orgasm, "you're going to have to fill me up! Fill up my fucking pussy, you hear me! Fuck my cunt full of your cum you fucking...fuck!" Cohesive thought took its leave of her, and I resolved to give her this last bequest.

Thinking I was holding out for fear of knocking her up, she insisted that there was no cause for concern when it came to "fucking an old whore like me", but I was loathe to let this end before I was good and finished using her.

The matter was not in my control for much longer though, and I grasped at her painfully as the all too familiar shocks of lightning began to crack their way along my spine.

"Yes baby, that's it!" She screamed, wise to my impending eruption, "fucking give it to me, right now, right here! Fuck that hot sticky cum right into me!"

And so I did.

Refusing to break the pace of my pounding rhythm, I fucked her right through the avalanche of delicious agony that plagued me, scooping great globs of the stuff in and out of her in equal measure, producing an outright mess of her glorious old pussy as my cum smeared itself into the hair around her slit.

Eventually, there was no more push left. The fuel gauge read empty, and I slumped across the wide expanse of her slick, sweaty chest. A brief clench of her muscles and she pushed my softening cock out of herself, breathing a raspy laugh as something hot ran down out of her.

"Fuck kid," she panted, "that was pretty good." I laughed into her chest, knowing the backhanded compliment to be at least half in jest. I slid off her, turning to paw at the cup dispenser on the water cooler in the corner. She stood and straightened with a crackling of old vertebrae, stretching her arms to the ceiling in a pose that let me admire her gorgeous body once again, and the bright red tracts I'd left on her ass. She rested her hands on her hips, looking around in amusement.

"Pretty good, eh?" I mused. "Does that mean you'll give me a recommendation after I get fired on Monday?"

She chortled, blowing hair out of her face.

"Fuck me like that again," she said with a crooked grin, "and I'll make sure you get out of this just fine."

It was a deal I could never refuse.

iwiwt
iwiwt
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5 Comments
AnonymousAnonymous4 months ago

Dude, your stories are awesome just to short.

AnonymousAnonymous10 months ago

amazing, liked it wholeheartedly

NoTalentHackNoTalentHack10 months ago

“ I'm not taking your pants off for you. This isn't fucking prom night." made me laugh out loud. Well done!

iwiwtiwiwt10 months agoAuthor

Thank you so much anon!

AnonymousAnonymous10 months ago

Superb

Fine pacing impressive context

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