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Staying Late on a Friday Night with a Sadistic Boss

Adam slapped the file down on his boss’s desk. “Here, I finished it. I’ll see you on Monday.” He sighed out, exhausted. Miss Devor had told him he had to finish the report before he left for the weekend because it was very crucial for “business reasons” or whatever. It had been a long week and he was ready to get home and crash.

“Just a moment, let me look it over first.” Miss Devor snatched the papers up from the desk and began casually perusing them.

Adam stifled a groan, “It’s there, Miss Devor. I double checked it.” He began inching towards the door to the office.

“Well then I shall triple check it.” She replied sharply, stopping him in his tracks with a glare from over her thick black framed glasses. “I’ve had to wait up for you to finish as well, so you can sit down and give me a *moment* while I make sure everything is in order. We all have places to be…” She added an additional note of annoyance to that last part.

Adam’s eye twitched. This type of behavior wasn’t new from his employer, but she seemed to be laying the sadism on particularly thick this time. He started wondering what could have made this frigid bitch extra pissed off tonight. Maybe she got stood up for a date with some rich douche or something. A cluck of her tongue in her mouth broke his train of wondered.

“This ‘to’ should have an extra ‘o’. Would you go fix it and reprint this page while I finish finding any other mistakes you’ve made? It’s the little things that investors notice when deciding if we’re worth their time.” She didn’t even bother looking up as the condescension oozed in her voice.

The blood in Adam’s head began to pulse. “Oh, I apologize. Here, let me see that and I’ll fix it right away.” She handed him the page and, looking over it with pursed lips, he set it down on her desk, took one of her pens, and drew a little circle at the end of the word. “There we go, all better.”

Miss Devor’s expression didn’t seem to change at all, being that it was already about as sour as it could get already. “Oh, we think we’re funny, do we?” She snatched up the page, crumpled it up, and threw it in the trash. “Attitudes like that are what go on performance reviews, ‘young man’. I suppose I’m already paying you enough that you don’t seem to need any more raises.”

Something snapped inside Adam’s brain. “How about,” he dropped the pen he was holding on the floor, “you take that extra ‘o’ and stick it in your retentive little anus. You can spend your time fixing any errors that offend your high sensibilities. It’s after hours and I’m leaving.”

Before he could turn to exit, Miss Devor shot up out of her seat and with surprising speed and grace, rounded her desk to glare directly in his face. With her high platform heels, she was just about eye to eye with him, taller with her high, tight bun, and her eyes were practically oozing venom.

“*Mister* Carter! I don’t know where this attitude is coming from all of a sudden, but it is very much not appreciated. You are lucky that I don’t simply have you clear out your desk and vacate the premises permanently. If security were still here, I would have them escort your insolent behind out of the building. You’d best take this weekend to adjust your attitude and consider very carefully if you wish to continue working at this office, or indeed in this career.”

That last part was the real threat. Being the close knit industry that it was, word could travel fast and blacklists were not uncommon in Adam’s field. Her abuse of authority was making him grind his teeth. He took a step closer to her, staring her down, “How about you take the weekend to consider why everyone who works here hates you, would throw a party if you drove your over priced, shitty electric car off a bridge. It’s no wonder there aren’t any family pictures on your desk since I can’t imagine even your parents want anything to do with you.”

The shade of red Miss Devor’s face turned was usually reserved for those who were witnessing their most hated enemy shtupping their mother in front of their whole family. Her fists and shoulders were visibly shaking at the insolence of one of her subordinates. “You… are… done… I will make it my life’s purpose to see that you never work in this field ever again, or at all if it is in my power.”

“Oh?” he was beyond caring at this point, “Well maybe I’ll start working in the fashion industry so that bitches like you don’t have to wear outfits that make you look like a complete cun…”

His words were sharply cut off by the impact of a heavy, thick soled toe slamming directly into his testicles at speeds unheard of. The overwhelming pain caused him to instantly throw up in his mouth a little as he toppled over, smacking his head hard on the desk and blacking out before he hit the floor.

​

Adam regained consciousness to the feeling of something jabbing him in the side in addition to his aching balls. As the information around him filtered through his brain, he realized that his hands were tied behind his back and his pants where down around his ankles. He was propped up in the corner of one of the unused offices that was nothing but empty file cabinets, a desk and chair. The sensation in his side was the heel of a shoe poking him in the ribs.

“Ah, you aren’t in a comma, perfect.” Miss Devor was standing over him, her normally studiously maintained bun somewhat disheveled, probably from dragging him into another room.

“Tha fuck is this?” Adam mumbled groggily. This wasn’t really a situation that he had ever imagined himself being in, and he had imagined himself leaping over the vegetable aisle at the store to save a hot girl from terrorist cyborgs. “Did you tie me up and pull my pants down?” The answer was fairly obvious, but he felt it needed addressing anyway.

“Your unconscious state allowed me time to ponder things, and I didn’t want you running off before we could have a little ‘chat’. And I pulled your pants down to make sure I hadn’t crushed your little grapes so badly that it would require a hospital visit.”

Well, at least she’d checked on him first before kidnapping him. “So, what? Are you gonna reveal that your an actual vampire or something? Or do you just want to keep me here until someone calls the cops on you on Monday.” He hoped that wasn’t the case, because, of the two options, the later seemed the most uncomfortable.

“Hmm, it seems the humor part of your brain isn’t located between your legs like the rest of it. No, I presume that after our meeting, you’ll walk out of here and show up promptly on Monday to resume your duties, *minus* the attitude.” There was an annoying smirk of superiority on her face as she said this.

“That so? You buy a mind control device on Etsy or take CIA brainwashing classes on zoom or something?” The CIA classes didn’t actually seem all that absurd for this control freak.

Miss Devor knelt down closer to Adam’s face, giving his nose a whiff of her expensive perfume. “Oh, I only plan to explain the facts to you, mister smart ass, and seeing as your such a ‘bright’ young lad,” she flicked his forehead with a manicured red fingernail, “I think you’ll understand the situation you’re in quite well.”

“Blackmail? Really? Gonna cook up a story about me to hang over my head?” Adam was a little disappointed in the banality of the reveal. Miss Devor was a ruthless dictator, but she was never stupid.

She arched a perfectly shaped eyebrow, “Oh, we’ve both been around long enough to know that I don’t have to ‘make’ anything up. Our society teaches men that they can get away with quite a lot before anyone does anything about it. It’s only when someone raises a big enough stink about it that anyone bothers to pay attention. The human resources guidelines might as well just say ‘Don’t get caught’.”

He found that he couldn’t actually argue with that. Even the people he generally liked working with would occasionally do things or make offhand jokes that should technically get them written up or fired, but no one was mad enough about them to actually draw attention to themselves over it, man or woman.

“So I laughed at a joke I shouldn’t have, or my eyes wandered when I was bored. You think anyone’s gonna do more than make us all go to another company sensitivity training that’ll get us out of work for an hour just so you all can say you did something? I’ll make sure to step back in line over that.” He thought if he laid the sarcasm on the last bit too thick and felt a little cringe. He struggled a little to test the rope (where did she get rope?) around his wrists and realized that it was an actual, real tie-up-the-hands knot. Little miss stuck up had apparently picked up some skills that would indicate a more adventurous side.

“Aww and punish everyone else on the company dime? Tch tch tch… No, I was thinking…” She moved her mouth close to his ear and whispered, “I would have them look in to you little interactions with Ms. McKay.”

This did actually shut Adam’s mouth. He’d had a crush on Lindsey since he started working there, and had often gone out of his way to just be around her.

Sensing his reaction, Ms. Devor increased the pressure, “I’ve noticed that you *have* spent a considerable amount of time over at her cubical, laughing at her jokes, taking the long way around to happen by for a chat. I’m curious to find out what *she* would say about all this attention, should be brought before dear old Beth for questioning. All positive, I hope? Or perhaps she wouldn’t even remember your name…”

Adam felt the blood start to drain from his face. If he let on that the bitch queen had him by the short and curlys, he’d be staying late every Friday until he died of a heart attack. Any attempt to compromise or plead would only be a sign of weakness. Maybe he could make her mad enough to give him a black eye or something that would be physical evidence of her treatment of one of her employees. He stammered out, trying to change the direction of the “meeting”. “S-seems like you’ve had plenty of time to watch the office drama while you sit back and let everyone else do all the work around here. Must be nice to be paid so much for doing nothing.”

She stood up and glowered down at him. “You have no *idea* what I do around here. Do you know how hard it is making sure that everything around here runs smoothly? Making sure there are clients coming through the door and money coming in so that you can collect your miserable paychecks? If I wasn’t watching you all like a hawk, you… *children* would be running around making pillow forts and playing seven minutes of heaven in the broom closet.” She brushed a stray strand of jet black hair from her face. “Do you think this is the first Friday night I’ve had to stay late getting things done?”

He honestly hadn’t really wondered about it. She may be the boss, but she wasn’t the one on top. The investors and CEO were the people that had to actually be satisfied with how things were going. He’d at all times just assumed that she had taken the easy rout and delegated everything to someone else like his past employers did. He’d underestimated her desire to micro manage.

“Oh, is it finally dawning on you that I might exist after you leave for the day? Typical.” She huffed. “I don’t like being a bitch, but so far it’s the only way I’ve found to make sure you people *listen* to me.”

Adam was starting to feel sorry for her, but caught himself as he remembered the interaction from earlier. “Oh, you don’t like it? You don’t get off having me go reprint one page because of a grammar error? No satisfaction at all from exercising your authority? I saw how you talked to Carol on Wednesday. You weren’t helping her do her job, you were putting her in her place.” He had her pegged, and the look on his face let her know it.

With a derisive snort, Miss Devor retorted, “That cow needs to learn that it’s a harsh world full of harsh people. I see it as doing her a favor. Some people pay good money to have their betters talk to them that way. Trust me, I know.”

“Yeah? So you’re ‘better’ than people who have actual lives outside of their jobs?” he said snarkily.

She planted a kick to his side, causing him to curl up like a caterpillar. “Fuck you! I have a more interesting life that you ever will you piece of shit!” That had obviously touched a nerve.

With a cough, Adam adjusted himself and sat up, staring up at her defiantly. “Go out to he clubs, do you? Pick up a new toy each night to try to fill that void inside?” There was that shade of red returning to her face again. It would be sort of hard for her to cover up beating the shit out of him. “I bet you do all the shit you think rich people do, only worse.” She was starting to look like she was about to turn assault in to attempted murder, but Adam didn’t care, she had this coming for a while. “You even have a tramp stamp. We’ve all seen it. Just like a basic bitc…”

Her fist collided with his face, causing him to taste blood. She knew how to punch just as well as she knew how to kick. Adam spat red on the carpet (again, more evidence for his case) and grinned up at her through bloodied teeth. “At least we know you can use more than money to try and solve your problems.” Her look of hatred suddenly turned to one of disgust.

“Is that… are you getting an erection?” She stared down at him. Adam looked down to see that he was, indeed, pitching a tent in his tightey whiteys. “Are you getting off on this?!” She added shock to her disgust. “Oh my… God!” She took a step back in revulsion.

Adam’s plan was starting to lean to the left as his legs shot up to try and cover himself. “So?! It happens some times and we can’t always control it.” Now it was his turn to begin turning red.

Miss Devor barked out a laugh. “Are you fucking kidding me? Oh, which is it that’s making you hard, insulting me or getting beaten up by a girl? You little pervert!”

Her insults weren’t actually helping his situation as he pressed his closed legs up against his body so she couldn’t see him twitch. “Shut up!” Was about the best he could come up with.

“Oh my God, you look absolutely pathetic. Do you need me to go get your emergency contact info and ‘cawll yo mommy’.” She began cackling at him, washing away any control he’d had of the situation.

The humiliation he was experiencing was about the second worst he would feel that night as she reveled in the glee of her triumph. “Yeah yeah,” he tried to sound as nonchalant as efficient, which wasn’t much. “Laugh it up. At least I can still get it up. Your pussy’s probably so dried up it sucks the moisture out of the room.” Sweet Christmas, he realized, they were both acting like children now.

“Oh, good one.” She continued to giggle at him, “Come up with that all by yourself? Or did your little friend down there help.” She leaned back on the empty desk. Now that she was back on top where she felt more relaxed, she sighed out, “Fuck my feet are killing me.” She casually kicked off her heels and let out a groan of satisfaction, wiggling her stockinged toes to help emphasis her dominance, and tease her captive more.

“Fine, we’re both pathetic, now how about you untie me and we both forget all this ever happened.” He hoped that in her glee she might play along.

“Tapping out now that you’re on the ropes? I guess when the going gets tough,” She pushed her smooth foot between his legs and pressed it against his hard-on, “this guy gets going.”

Adam swallowed the moan that he almost let out as he felt the pressure on his cock. “Fuck you, this is still assault and kidnapping. A little more severe than some office flirting, and now I have the blood and bruises to prove it.”

This, at least got her to stop laughing hysterically as she composed herself. She examined him for a minute, thinking to herself. “Hmm, maybe your right, but I still feel like I need to teach you who’s on top in this ‘professional’ relationship. You said some pretty nasty things about me, and I intend to make you feel like shit for it.” She placed her finger on her crimson. pouting lips, considering what to do next with her captive. Something seemed to click in her head and her eyebrow shot up.

“I wonder why you haven’t asked Miss McKay out yet, you two seem chatty enough on company time.” She watched his reaction, digging for clues with her eyes. Whatever the look on his face was, it gave her everything she needed. “Or maybe… You did, and she turned you down…”

His eyes shot to the side, looking away. This all but confessed out loud the truth to her. “You did, didn’t you. Oh my! You like her and she rejected you.” The grin spreading across her face reminded Adam of the Grinch Who Stole his Balls. “Aww, what did she say? ‘I don’t date coworkers’? ‘I’m just not in that kind of place right now’? Or did she just drop the pretense and tell you you’re just not her type.”

Whether any of those were the actual response, it didn’t matter. They might as well all have been the same answer. Adam stared up at his boss with hatred at how she was making him feel, the internal wounds she was tearing open with her verbal claws.

“Has it been a while? Since a girl said yes? Months? Years? A nice ‘boy’ like you, still single. Whatever could be *wrong* with you.” She twisted the emotional knife just right to finally break him. Adam stifled a sniff as he felt hot tears well up in his eyes. She’d found the nerve and tweaked it with surgical precision. The humiliation and taunts had opened the path directly to his weakest points. It wasn’t even that someone had uncovered his insecurities., it was that she had found out. All he could do was silently stare at the floor.

Miss Devor gave a satisfied grunt, confident that she had felled her prey. “So, you are going to show up on Monday, resume your work, and follow every instruction I give you to the *letter*. Are. We. Agreed.” Adam remained silent but gave a slight nod. At this point he was eager to capitulate to just about anything to get out of there and go home to curl up in a hopeless ball in the dark. “Very well, roll on to your stomach,” her voice emphasized the submissiveness of the position, “so I can untie you and let you crawl off to sulk in a corner somewhere.”

Adam did as he was told, and was released from his bindings. He stood up, head still hanging down, and pulled up his pants. He didn’t even bother buckling his belt as he stood there, trying to will himself to move. Finally, he looked down at her as she still smirked, her hands on her hips in a pose of victory. “You know, what I said was true. You do enjoy being cruel, even if you lie to yourself about it.” Her smile dropped a little, but she just regarded him coldly. “I fucking hate you, but I’m gonna give you some advice. You’re gonna keep treating people like shit because it’s the only way you know how to interact with them, and you’re gonna be even more alone than me.” Her smile was now completely gone. “Once you get old and no one thinks you’re hot anymore, you’re gonna need other people because guys aren’t gonna just hand you things like this job anymore. The best you can hope for is that you die suddenly in an accident before you get too depressed and kill yourself…”

He turned and started leaving he felt hands grab his shoulder and spin him around, slamming him against the wall. Without her shoes on, she was significantly smaller than she was before, now almost a head shorter, but you wouldn’t know it by the way she glared up at Adam. The look of raw mixed emotions on her face shocked him even more than her ability to body him, her arm pressed against his throat.

“You fucking think you know fucking shit about me?” None of the cold mask she was wearing before remained. Tears had begun to slowly roll out of the corners of her squinting eyes. Adam instinctively reached up and grabbed her arm, letting his pants fall to his knees, but that just made her push harder. “You don’t know fucking anything about what I’ve had to put up with to get where I am. To not have to really on my parents or some shitty ex husband.” Adam didn’t even know she’d had a husband. “I’ve had to put up with so much shit to get to the position I’m in. You have no fucking IDEA!”

She was breathing heavily, her face scrunched up, tears causing her mascara to run down her cheeks. “You think I treat you like shit?! The people I’ve had to work for to get here didn’t even treat me like I was human! Every fucking day was a battle to not be alone in the same room with some of them, or figure out how to avoid their invitations without getting labeled a stuck up prude by the people in charge of deciding whether to give the promotion to me or someone with one of these,” she reached down with her other hand and grabbed his crotch, “who laughed at their stupid jokes?” She let out a wracked sob, “Shit, maybe I *am* just as bad, I don’t know. It’s not like I want to be…” She was staring through his chest at nothing as her mind tried to process what she was feeling.

She stepped away, her entire body trembling. Then she glanced up directly at him, with a slightly unhinged look in her eye. Before he could say anything, she grabbed his hands and put them on her throat. “You say you hate me so much, why don’t you do something about it, huh?” Adam tried to pull away, but she just gripped him tighter. “Why not take it out on me, just like my husband,” She squeezed harder, “Just like dad.”

“You’re fuckin crazy!” Adam was struggling to get away from her before she could escalate things, but he wasn’t fast enough. She let go with one hand and slapped him hard across the face.

“You little bitch! No wonder no one wants you, you pathetic shit!” She slapped him again, stunning him in place as she screamed at him. “Lindsey could never fuck a disgusting maggot like you, you worthless asshole!” The third slap succeeded in getting him to where she wanted him. He wrapped both his hands around her neck and picked her up, slamming her down on the desk.

Miss Devor grunted from the impact, but her groan of pain turned into a maddened, strangled giggle as she maintained eye contact. Instead of fighting his hands, she reached down and pulled up her skirt so Adam could get a clear view of her black thong underwear, spreading her legs wide so he could see the dark hair of her trimmed cunny peek out from the edges. She reached down again and groped his bulge, trying to jerk him off as best she could while being choked.

“Yeah, let it out! Show me what a tough guy you are!” she managed to choke out. Adam couldn’t believe what he was doing, closing off his own boss’ airway while she fondled his throbbing cock. The realization got him to relax his grip enough for her to gasp in air before she yelled, “Fuck me you fucker, fuck your boss with your pervert cock!” Her hands yanked down his underwear, causing his rock hard erection to spring out, sending a dab of pre-cum sailing through the air and landing on her leg.

Roughly he tugged her panties to the side, her slit already glistening with juices, and pulled her to the edge of the desk so he could shove himself all the way inside her in a single stroke. The moan she let out as he stretched her open was a perfect mixture of pleasure and pain. “Fuck! You’re fat dick is splitting me open!” Her hands reached down and grabbed his ass, her nails biting into his skin. “Keep choking me while you pound me!” She commanded.

He placed one hand on her throat, squeezing, but not nearly as hard as before, while his other hand desperately groped her breasts, the same one’s he’d seen almost every day bouncing slightly as she marched between the cubical to administer her domination.

Adam groaned, “Oh fuck, you’re so hot inside.” Her muscles, strengthened by a regiment of Kegals, clenched down on him like a vice, almost making it impossible for him to move inside her. He could feel her short, soft pubes brushing his shaft as he moved.

“What am I? Tell me what I am!” She demanded through clenched teeth.

“You’re a fucking bitch! You’re a fucking whore bitch with a slutty little body and a cock hungry cunt!” He yelled, forcing himself as deep as he could. “Fucking showing off to every one in the office what a dirty cunt you are!” He felt her suddenly get wetter as her walls started to spasm. Her eyes rolled back and she stuck her tongue out, panting while she came on him.

“Oh god! Oh god! Yes, I’m a filthy slut! Fuck my bitch cunt, daddy!” He felt a finger start to push up into his anus, causing him to involuntarily clench as she milked his cock with the same amount of precision that she used to break his spirit.

“I’m gonna cum! I’m gonna…” He was interrupted when she shoved him off of her and hopped off the desk. Her slender fingers wrapped tightly around the base of his shaft, squeezing hard to keep even a single drop from escaping. Adam cried out at the pain of his blocked orgasm.

“Not yet you little shit! You’re gonna cum up my ass and get your dick all filthy, you dirty fuck!” She lobbed a gob of spit right on his cock and rubbed it around with the other hand, maintaining her improvised cock ring. She then got another wad of saliva on her hand and rubbed it over her asshole. “Now fuck my ass and make it hurt you little pussy bitch!” She bent over the desk, pulling her thong down and spreading her cheeks wide with her hands.

Desperate to cum, Adam started pushing the throbbing head of his cock against her tight sphincter and felt her pressing back up against him. Miss Devor grunted in satisfaction when the head popped into her, opening her smaller hole to the rest of his rod. She yelled at him to keep going as he continued to apply pressure, sliding steadily deeper and deeper into her bowels.

“Oh fuuuuuuuck, I’m soo tight…” her moan was long and low as she felt him filling her up until his balls were brushing up against her pubic hair. He started moving slightly at first, almost rocking in and out before he began sliding out further and thrusting back in. “It hurts…” she whined, “Your cock is hurting me…” but the way she said it made it sounds like anything but a complaint.

Adam didn’t even feel the create up this time as his seed rushed to escape his balls, spraying out into the tightest hole he’d ever felt. All he could do was moan as he almost collapsed on top of his boss, still pumping loads of hot mess inside her stretched out ass. She clenched hard to draw out as much as she could, determined to milk every last drop from him before he could pull out.

Miss Devor reached down and started fingering her pussy frantically, using the excitement of the thick load sloshing inside her to get herself off before he could pull out. “Stay in there! Stay in there while I cum again.” She desperately pumped her fingers in and out, moaning like an animal as she forced another orgasm so hard her clenching muscles pushed him out of her along with a splash of his cum on to his leg and dribbling over her pulsing pussy lips and hand.

Her ass gaped open for a moment before slowly closing up around what remained of his seed. Both of them were panting, exhausted and drenched in perspiration. Miss Devor could feel the bruising start to form on her neck and Adam’s cheeks were pink from the burst capillaries from her slaps, along with a bruise on the side of his face from her punch.

She turned around, her makeup a mess of tears and sweat, more cum leaking out on to the desk as she sat against it. “You asshole, I haven’t cum that good in ages.”

Adam nodded back. “Me either. That was so fucked up.”

Miss Devor licked her nectar from her fingers and grinned. “I guess this means I’m going to be keeping you late after work a lot from now on.”

“How about…” Adam was still panting, “we just go to one of our homes and fuck like normal people instead, Miss Devor.”

She blushed a little and was suddenly overcome with a timid, shy countenance never before seen within that office. “You can call me Jane when we’re alone… If you want…”

NSFW: yes

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