Upward Ambition Ch. 02

(Author's note: reminder that while non-con/reluctance fantasies can be fun and sexy—they should remain purely fantasy. In real life, unpressured and enthusiastic consent is absolutely paramount.)

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I am up half the night, trying to convince myself to quit my job like a sensible person and never look back. The problem is that I've never been particularly sensible. Besides, if I quit now, then wouldn't everything I endured in Derek's office be for nothing? Really, wouldn't the sensible thing be to enjoy the fruits of my labor, i.e. my menial, shit-for-pay job? That's the reasoning that convinces me to set my alarm for an hour early the next morning. Definitely that, and not the fact that I spent a long, very confusing time in the shower when I got home, jerking off to the memory of cold grey eyes, smirking mouth, and the cruel grip on my hair.

My bruised ass hurts so bad the next morning that I end up bringing a pillow to sit on in my car. I have no idea how I'm going to make it through the day, because I have no intention of bringing the pillow into work. Not only will there be the inevitable hemorrhoid jokes from the guys in sales, but Derek will know the truth, and I can't stand the thought of my compounded humiliation. I would honestly prefer the hemorrhoids.

The office is empty when I arrive. We're in our off-season, so there isn't much use for overtime. Small mercies. I drop off my bag and coat at my cubicle. Before I head next door, I take a moment to straighten my tie, and I'm struck by the unwilling memory of Derek's grip on my tie the night before, holding me captive while he choked me on his cock.

I chug some water from the bottle on my desk and knock on my boss's door.

"Come in."

I enter and shut the door behind me. Derek is not at his desk, where I expected to find him. Instead he's seated on the leather couch on the far wall, one leg crossed over the other, thumbing through the latest issue of Technology Today, utterly at his leisure.

"You're late," he says, without looking up. I notice that his hair is still slightly damp from the pool where he works out every morning. Does the man ever get any rest?

I glance at the clock. 7:02 a.m..

"By two minutes," I say.

Derek lets out a longsuffering sigh and sets the magazine to the side. Only then does he deign to look at me.

"I don't usually like to discuss money; I find it to be in poor taste. But you should know that one minute of my time is worth half your monthly salary." His tone is casual, almost pleasant, but he isn't smiling. "So will you be foregoing your paycheck this month, or will you be accepting the punishment for wasting my time?"

Derek isn't a man given to hyperbole, but surely he's exaggerating. He must be.

Then the rest of his words sink in. Punishment. Fuck.

I open my mouth. Close it again. I'm having trouble remembering why I showed up this morning.

"The longer you stall, the more minutes you waste." Derek leans back and rests one arm on the back of the couch, as if to show me he's more than happy to wait all day while I rack up more debt.

"I'll take the punishment." I have to force the words out of my mouth. They're even harder to say than they were last night, now that I'm intimately acquainted with what exactly a punishment from Derek Harrow entails.

Derek uncrosses his legs and straightens, but he doesn't stand up.

"Come here," he says, and I obey. My ass is already aching in anticipation. "Drop your pants."

"W-what?"

Derek doesn't bother to respond, just levels that icy stare. This is a man accustomed to getting his way, no questions asked. Hands shaking, I fumble with my belt. I undo my button and zipper, but before I go any further, my gaze flickers uncertainly toward the door. It's unlocked.

"If you're worried about us being interrupted," says Derek coolly, "then I suggest you hurry up."

Bastard.

I bite my lip and try to direct my thoughts elsewhere, so that I don't have to bear witness to what my own hands are about to do. I pull down my pants. I'm wearing tight boxers, but my shirttails cover my crotch, so it's not like I'm on display. Somehow that doesn't make it any less embarrassing. (How I can still feel embarrassed, when twelve hours ago I was jerking myself off for his amusement, is beyond me.)

I expect to be told to bend over, but instead Derek grabs my wrists and yanks me down over his lap. I flail in momentary confusion, until he clamps his hand on the back of my neck in an iron grip. I drop limp as a kitten.

"Good boy," he says. His grip loosens, and he strokes his other hand gently down my back. The sensation is as comforting as it is unexpected. I'm shamefully aware that if I had the ability to purr, I probably would.

He shifts his knees until I'm arranged to his liking, my ass up in the air, my cock pressed painfully into his thigh. I brace my hands on the floor. I know what's coming next.

"Twenty strokes for two minutes wasted," he says, as he pushes up my shirt hem. "I think that's fair, don't you?"

It takes me a second to realize the question isn't rhetorical.

"Yes sir," I manage. My mouth is already dry again.

"Don't forget to count." He brings his hand down on my right cheek with a resounding smack. Even braced as I am, the impact takes me off guard and I jerk away instinctively. My boss holds me firmly in place.

"One," I say, before he can correct me. Smack. "Two."

Fuck, is it possible that his hand hurts worse than the belt? Or maybe it's just that the spanking is on top of last night's whipping.

Smack.

"Three."

Smack.

"Four."

I've learned from my previous mistake, and I'm careful not to lose count. But by the time we're halfway through, it's getting harder and harder to concentrate. Derek is spreading his blows evenly for the most part, though he does seem to pay special attention to the tender curve where my butt meets my thighs. Worse than that is the bright spot of sensation where my pelvis is grinding into his leg with every blow. I try not to think about it, but it's building toward a fever pitch, straining my focus between pain and pleasure.

Smack.

"Nineteen."

Smack.

"Twenty."

Tears spring to my eyes on the last blow, but I swallow down the sob before it can escape. My ass is on fire, and the heat is flooding across every inch of my skin. I wish Derek would push me off, so that I can pull up my pants and make my escape while I have even a modicum of dignity intact, but no such luck. Now that my punishment has been meted out, he seems once again at his leisure. I shiver as he slips a hand down the waistband of my underwear. His fingers are frigid against my hot, pulsating skin.

"You show color very well," he remarks, almost to himself.

I'm not sure what I'm supposed to say to that, so I say nothing. I'm panting with exertion, even though I've barely moved a muscle. I can feel his own hardness against my ribcage. I wonder if he's going to make me suck him off again. If I do a good job, I wonder if he'll let me come.

I hate myself for wondering that.

This whole time, my boss has been running his fingers over his handiwork. Occasionally he'll stop and pinch, making me jump and groan. I lose track of how long I've been there, sprawled over his lap while he fondles my buttocks. Then his fingers dip into my crack. I tense up. I've never been touched there before. This is new, terrifying, impossible territory. It's like every nerve in my body freezes, and every iota of my focus zeroes in on those fingers. It's like nothing else in the universe exists. One finger presses down, ever so gently, on my hole.

My body reacts before my mind even realizes what's happening. But once my mind catches up, it's in full agreement. I jerk violently away from his touch. I try to stand, but with my pants around my ankles, I only manage to land hard on my ass. Fuck, that hurts. I don't pause to dwell on it. I'm in full flight mode.

I yank up my pants and finally make it to my feet. I manage to pull up the zipper, but my fingers are trembling so hard I can't get a good grip on the button. I gasp for breath, trying to master myself enough to get the hell out of this office.

Derek hasn't moved an inch. He's just watching me with a flat, almost indifferent gaze.

"I'm leaving," I manage to sputter, as if it's not already obvious. I thought I could handle it. I thought I could weather his sick punishments enough to keep my job, but this is too much. I'll find a new job and start over, even if I have to lose my apartment, even if I have to crash on a friend's couch and start from scratch. Derek Harrow may be accustomed to always getting his way, but in this he is going to be disappointed.

"Our ex-client is suing Fultech for lost revenue," he says, apropos of nothing. His tone is as impassive as his expression. "When all is said and done, the amount will be in the millions."

I swallow hard. I struggle to keep my own expression under control.

"So?" It's not my problem. Fultech Corporation isn't my concern anymore. I'm leaving.

"I misspoke," he says. He stands and drifts past me to his desk, where he sits on the edge, arms crossed. "They're suing you for millions."

I think I black out for a second. It takes a long time for my brain to reconnect with my mouth.

"Me?" It comes out as an embarrassing squeak.

"Since you are an employee of Fultech," he says, "the company absorbs the liability. We have insurance for this sort of thing, and attorneys on retainer who are quite good at their job. I imagine we'll reach a settlement quickly."

I'm able to breathe again. Right. Of course. This sort of thing happens all the time. Of course the company has protections in place. Nothing to worry about.

"Then again," Derek goes on, almost thoughtfully, "if you are no longer an employee of Fultech, I suppose the liability falls to you. Even if we end up being stuck with the bill, I can assure you that our insurance carrier will be subrogating against you for the full amount. They have excellent attorneys as well, I imagine."

I blink at him, unable to wrap my head around what he's saying.

"If you walk away now," he says, very slowly, like he's speaking to a child, "you are going to end up in court with your cheap, shitty lawyer, and you are going to lose. Then every spare penny you make for the rest of your miserable life is going into someone else's pocket."

I blink again. My heart is pounding so hard I can feel it in my head.

"I don't have a lawyer." I can't think of anything else to say.

Derek smiles. It's not a pleasant sight.

"Then I suggest you do as you're told."

I shake my head, still clinging to one last shred of hope.

"You can't do this—it's blackmail. I'll go public. I'll have you arrested."

His smile doesn't budge. If anything, it widens.

"In that case, you'd better find an ad on a bus bench somewhere and hire yourself a lawyer. Because you don't have a shred of evidence, and once my attorneys clear my name, I'll be taking you to court for slander. I don't like your chances, but by all means..." He gestures toward the door. During this entire speech, his voice has remained perfectly even, his expression perfectly calm.

The full weight of my situation finally hits me. I think I might pass out, but my brain stays stubbornly conscious. Derek straightens and walks toward me. When he stops, he's towering over me, so close I catch a whiff of his aftershave. I don't realize how much I'm trembling until his hand, rock steady, lifts my chin. My breath catches in my throat. My eyes meet his.

"I don't want to destroy you in court, Jack," he says softly. His thumb trails along my jawline, sparking frissons of sensation in its wake. "I will if I have to, but the ways I prefer to destroy you would be infinitely more pleasurable—for both of us."

With his other hand, he palms my crotch. His eyes never leave mine. He gives me a squeeze, and a strangled moan escapes me before I can stop it. Despite myself, despite everything, I'm so turned on right now I can barely stand it. My cock responds eagerly to his touch. Every inch of my skin is bright-hot and burning. I'm leaning into him, like a flower to the sun, like a moth to the flame.

Then, without warning, he steps back. I wobble dangerously—my legs suddenly feel like jelly. Derek leans back against his desk, as unbothered as if we were just discussing quarterly earnings. I hate him so much right now. I hate him, and yet I have no choice but to stay.

Maybe he sees that I've accepted my fate, because the corner of his mouth twitches in a smirk. Motherfucking bastard.

"Take off your pants," he says. "Underwear too. Then bend over." He pats the desktop and straightens.

Numbly, I do as I'm told. I don't know if I can take another whipping, especially on my bare ass. But it's not like I have a choice in the matter. While I'm undressing my bottom half, Derek goes to one of the bookshelves and retrieves a black lacquered box that's a little smaller than a shoebox.

I rest my palms and forearms on the desk in the familiar, humiliating position. The cool mahogany raises goosebumps on my febrile skin. Derek sets the box on the desk right in front of my face, so that I have a perfect view when he opens it. There are only two items inside. The first I recognize immediately as a bottle of lube. The second takes me a few more seconds to place, and when I do, my heart drops into my stomach. A butt plug.

"Spread your legs," Derek says, and when I don't immediately comply, he smacks my ass hard. "Now."

I yelp and widen my stance, unable to take my eyes off the bright pink silicone plug. It's not massive, but it's not tiny either. Both my lungs and asshole seize up in instinctive terror, as Derek picks up the lube bottle and disappears behind me. I hear a squirting sound, and a couple seconds later, the cold, wet sensation as Derek slides a finger in between my crack.

I manage to stay still while his finger circles my pucker in light, teasing strokes. But at the first hint of intrusion I can't stop myself from crying out. I try to straighten up, but Derek is faster than me. His hand in between my shoulder blades slams me back onto the desk. His feet are planted between my ankles, preventing me from closing my legs. I let out a whimper.

His finger penetrates my hole, only to the first knuckle, but I still feel unbearably violated. I jerk involuntarily when it reaches the second knuckle. Derek only presses harder on my back, keeping me down.

"It will hurt less if you relax." He doesn't sound like he particularly cares one way or the other. The ways I prefer to destroy you would be infinitely more pleasurable.

I try to relax—I do. But it's easier said than done, especially when he slides his finger in the rest of the way and begins to swirl it around. It's not quite painful yet, but it's such an alien, uncomfortable feeling that I can't help but squirm. Abruptly, the finger pulls out. The relief is short-lived, because he spanks me again, so hard that tears spring to my eyes.

"Stay. Still."

"I can't," I whine.

"What was that?" He delivers more blows, each more painful than the last.

"Sorry—I'm sorry!" I gasp out. "I'm sorry, sir. I'll stay still."

He doesn't reply, but I hear the squirt of more lube and suddenly there are two fingers rammed up my ass. I bite back a scream, barely. My hands curl into fists, nails digging into my palms in a desperate attempt to distract myself. Sparks of pain erupt around my hole as Derek scissors his fingers, stretching it. When he adds a third finger, I have to bite down on my own knuckles to keep myself still.

For a while I know nothing but misery, and then his fingers press against a spot inside me that is like a shot of pure ecstasy through my veins. I jerk wildly again, this time from pleasure instead pain. I can practically hear Derek smirking behind me as he, quite intentionally, massages that same spot. I let out a sound between a moan and a sob, unable to stop my body from writhing. The sudden bliss is somehow intensified by the accompanying pain, rather than dulled by it. My cock, which had been inexplicably at half-mast during this entire ordeal, is now straining up against my belly, aching for release.

"I hope you remember the rules, Jack," Derek says in silky tones, as he continues to assault me with pleasure. "Sluts must ask permission to come."

"Please," I whimper, beyond all dignity. It's taking every ounce of willpower I possess keep my hands on the desk and off my cock. "Please let me come, Mr. Harrow."

"No." He withdraws his fingers, and I sob at the loss. I've lost my fucking mind. How does he keep doing this to me? I'm so caught up in my own stymied desire that I don't even notice when he picks up the butt plug.

But when the cold, unyielding shape—so much larger than a finger—presses against my hole, it's impossible to miss. Oh god, no.

"It's a pity you had to waste so much time this morning," Derek says, rubbing the plug against my pucker, giving me a full idea of its girth. "This would have been much easier for you, with more time to prepare."

He does not waste anymore time. He rams the plug in to the hilt. My vision goes white as the pain explodes through me. I don't think that any amount of time could have prepared me for that. The butt plug may not be overly large, but it's still a violation of epic proportions. When I come back to my senses, my eyes are blurred with tears, and my throat is raw from a scream. It takes me a second to realize that the reason I'm having trouble breathing is that Derek's hand is clamped over my mouth, muting my cries.

He is leaned close to my face, shushing me softly. His other hand is rubbing soothing circles on my back.

"Good boy," he says into my ear. "You're such a good little cockslut."

He drops his hand, wet with my tears, down to stroke my penis. It had begun to flag, but his touch coaxes an immediate response. I'm shaking so hard that I have no doubt the desk is the only thing keeping me from collapse.

There's a knock on the door.

Derek's hand pauses in its ministrations. I whimper, beyond caring about anything except my aching, weeping cock.

"Don't you dare move," he says, as he straightens. I drop my forehead against the desk and squeeze my eyes shut, trying to regain any measure of control over myself.

I hear Derek open the door, and my eyes spring open. I turn my head, but otherwise don't move. The desk is angled so that if Derek opened the door another few feet, whoever is standing outside will have a perfect view of me bent over the desk, naked from the waist down, dripping tears with a hot pink plug in my ass.

I'm hot all over. My ass—inside and out—is a constant, throbbing ache. I don't dare move.

"Sorry to bother you this early," comes the voice from outside. I recognize it as Penny from accounting. A pretty, petite redhead that I've been flirting with for the past year. Recently, I'd even been making some progress. "Jack's not at his desk, and I just wanted to remind you that I need your monthly expense report before nine to make the deadline."

"No problem." Derek sounds for all the world like she'd just interrupted him in the middle of some inconsequential paperwork. "I'll have Jack deliver them as soon as possible. Or if it's easier, you can come in and wait while I dig them up."

My heart skips a beat. I can't believe what I'm hearing. Derek is still leaning against the door frame, cool as a cucumber, with only a few feet of wood separating him from scandal and me from utter humiliation.

"No, that's fine," Penny says. "Just send Jack my way when you can."

It's not until Derek shuts the door again and turns around that I'm able to breathe.