Upward Ambition Ch. 03

(Author's note: this chapter ends on a bit of a cliffhanger, but I promise the next installment is coming very soon! Reminder that non-con and reluctance fantasies are only sexy in fiction. In real life, always make sure you have enthusiastic, unpressured consent. Also, if you don't find non-con/reluctance sexy...maybe you are in the wrong section?)

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The next few weeks pass in a blur of hot humiliation and aching need. I spend most mornings on my knees in Derek's office, practicing my cocksucking skills. Most afternoons I'm bent over his desk or his lap while he punishes me for whatever my latest infraction is. Sometimes he allows me to have my own release. Mostly, he doesn't.

The butt plug and I become even more intimately acquainted. He doesn't make me wear it every day, but on the days he does, he uses the vibration as a dog whistle. I come whenever I'm called, no matter what I'm in the middle of. I know better than to keep him waiting. People start to comment on how well I seem to anticipate when Derek needs me. I'm there before he even has to pick up the phone.

It's not long before I am summoned to the human resources department, where I'm given a nice raise. Not enough to go wild, but enough to start paying down some of my credit card debts. The HR lady asks me how I like working for Derek, and I tell her he's the best boss I've ever had. Somehow I doubt any other answer would be acceptable. There's an even bigger butt plug in his office that he showed me once, although he has yet to inflict it on me. He made me get on my knees and thank him for not shoving it in my hole. As debasing as it was, my gratitude on that front was not feigned in the least.

By this point, I know his cock better than I know my own. I could trace the curves and veins from memory of my tongue alone. I know exactly where to lick and how much pressure to use. He likes when I bury my face in his crotch, slurping on his balls until I'm a sweaty, drooling mess. He loves when I deepthroat him of my own volition. (I haven't completely conquered my gag reflex yet, but I'm getting there.) He loves it more when I try to pull off, but he grips the back of my hair and holds me in place while I cry and choke for air, my nose buried in his pubic hair, my eyes wide and pleading. I whimper and moan while he calls me a filthy, desperate cockslut. Usually he makes me swallow, but every once in a while he likes to shoot his load all over my face, so that I have to find a way to the restroom to clean myself off without anyone seeing.

One day, after a particularly grueling shareholder meeting, he has me on my knees under his desk, sucking him off while he finishes some paperwork. I'm not sure how long it's been—close to half an hour at least. His impeccable self-control extends to every aspect of his person, and he enjoys drawing my humiliation out as long as possible.

There's a knock on the door. I slide my mouth off his shaft with a pop, expecting him to let me up. Instead he smacks my cheek and drags my face back down to his crotch.

"Did I tell you to stop?" he asks crossly. Then he calls out: "Come in."

The door creaks open. I don't know what else to do. I wrap my lips around his head and suckle as quietly as I can. Derek's desk is massive and solid. From the front side, you can't see underneath. Theoretically, the only way someone could see what's happening in Derek's lap is if they came around to the other side. Theoretically.

"Well that was a shitshow. Fucking shareholders." I recognize the voice as Kevin Grant, the CFO. There's a creak of leather as he sinks into one of the chairs across from the desk.

I relax marginally and slowly, carefully, take more of Derek's shaft into my mouth. The last thing I want to do is trigger my gag reflex, but I know there will be hell to pay if I slack off on my duties—regardless of who's in the room with us.

"You told me the mid-year earnings were as expected," Derek says. His tone is mild, but there's an undercurrent of danger that I recognize immediately. A shiver runs down my back. He is not happy, and that doesn't bode well for anyone—but least of all me.

"And expectations were shit. What am I supposed to do about it?"

"Your job, one would hope."

Kevin laughs and says something about not being able to turn lead into gold. I lose focus on the conversation as I return my attentions to my boss's cock. I don't dare attempt to deepthroat him right now, but I nurse the first few inches as thoroughly as I can, until finally he grabs a handful of my hair and yanks me off. I bite back a yelp and look up beseechingly, but Derek's gaze is fixated on Kevin. He does widen his legs, ever so slightly, and I take my cue to dip down and tongue his sac. I mouth his balls, first one, then the other, keeping my breathing as slow and quiet as humanly possible. I'm stewing in the moist warmth of his musk and my own sweat, but I stay on task.

The conversation seems to be wrapping up. Kevin's chair creaks again as he stands up.

"I'm just saying, if you consolidate some personnel—here and abroad—it would help the bottom line."

"I appreciate your suggestions on how to do my job," Derek says icily. "Maybe if you put half as much effort into doing yours, we won't get our asses handed to us in the next shareholder meeting."

"Okay, okay, I've said my piece." Kevin's tone is conciliatory, and I imagine him holding up his hands in surrender. He's the only one with enough clout in the corporation to go head to head with Derek Harrow, but even he knows better than to push his luck. "By the way, where's that assistant of yours? He was supposed to bring me the Langman file hours ago."

"He's on an errand for me." Derek's fingers slip silkily through my hair as I continue to suckle his balls. "When he gets back, I'll send him your way."

"That one's got a tight little ass on him, doesn't he?"

I freeze. My foggy mind struggles to make sense of what I've just heard. Derek's grip on my hair tightens in painful warning, and I force my lips back into motion.

"Mouth like a whore, too," Kevin goes on, as casually as if he's describing the weather. "I can see why your dad kept him around."

I'm indignant, even as I keep at my hot, eager sucking. Mike Harrow never so much as cast an inappropriate look in my direction. It's his son who's the egomaniacal, perverted control freak.

"I hadn't noticed," Derek says. Kevin scoffs, clearly not buying it. Derek ignores that and continues, his voice perfectly level. "But hands off, Grant. Good help is hard to find."

"Whatever." The door opens. "I'll be waiting for that file. And please at least consider the personnel issue."

Derek waves him off. The door clicks shut. I don't even have time to blink before Derek has taken my head in a steely grip and shoved his cock down my throat. He jerks his hips in a frenzy of pent-up frustration. I steady myself with my hands on his knees, but I know better than to try to push away. He stops when he's fully seated in my mouth. My throat spasms uncontrollably and tears well in my eyes, but I force myself to meet his waiting gaze.

"If you ever let him so much as touch you," he says, his voice quiet but not soft, "I swear to god I will strap you to this desk and beat you senseless. Then I'll fuck you awake and do it all over again. Understand?"

The only reply I can make is a low, anxious whine. I guess that's enough because he starts face-fucking me again, going harder than he ever has before. Fortunately, after such an extended buildup, he doesn't last long before he explodes in my mouth. As I gulp it down, I swear I can taste his pique along with his cum. I have a feeling if I so much as lose a pen today, I'm going to be getting a prelude of that beating anyway.

Once he's finished, I try to pull off, but he won't let me.

"I haven't dismissed you," he says. He leans back in his chair and starts typing again on his keyboard. "Kevin can fucking wait."

And so I stay where I am, stiff-necked with my face buried in his crotch, my throat sore and coated with semen. The only sounds are the click-clack of computer keys and my own labored breathing through my nostrils. He doesn't give me permission to move, so other than the occasional involuntary swallow, I remain perfectly still.

He keeps me on my knees as his cocksleeve for another hour before he finally releases me to get back to work. Kevin Grant scolds me for taking so long with the file, and I can do nothing but stand there and absorb the blame. The whole time I'm thinking about what he'd said about my tight ass and my whorish mouth. When I finally turn to leave, I swear I can feel his leer on my backside. I suppose I should be grateful that he didn't "drop" something on the ground for me to bend over and pick up.

The next day, Derek informs me that he's going to the London office for two weeks. I expect him to tell me I'm coming with him. He has a private jet, and I have no doubt he would love to make the trip with me as his private flight attendant and fucktoy. But I'm surprised to learn that I'll actually be staying at the office to hold down the fort. The thought of two whole weeks without Derek, without being belted or plugged or forced to suck cock, is enough to make me giddy. Maybe I'll spend my evenings at the bar with friends instead of on my knees in Derek's office. Maybe I'll even be able to schedule a date with Penny from accounting.

Before he leaves for the airport, he gives me a company laptop and orders me to keep it at home, turned on, so that I'll see any emails from him immediately. That doesn't entirely dash my hopes at freedom, but I do start to get a sick feeling in my stomach.

Sure enough, that night when I get home and set up the laptop on the cluttered desk in my bedroom, an instant message from Derek pings.

You're late.

I hadn't been aware I was on a timetable. I consider telling him that, but my self-preservation kicks in.

Sorry sir, I type instead.

I sent you a package. You should have received it by now.

There had been a padded manila envelope with the mail, with a laser-print label and a P.O. Box return address. I'd assumed it was the new earbuds I'd ordered last week—a small reward to celebrate my raise. I open up the package, and instead of earbuds find a bottle of lube and a black silicone butt plug. Or at least, I think that's what it is. It looks like a cross between a plug and a dildo. The shaft is about four inches long, with a ribbed section at the base that expands and contracts almost like a slinky toy. There's a narrow neck and a handle at the bottom, like a plug. It's about the same width as the pink plug, but much longer. My insides are starting to hurt just looking at it.

The computer pings with another message.

Put it in and send me a picture. You have two minutes.

I blink at the screen, wasting almost fifteen seconds while I try to convince myself I must be dreaming. Then I snap out of it and shuck off my pants and underwear. I slick up my fingers with lube and try my best to prepare my asshole for the intrusion, but he's never made me do this myself before, and I can barely convince my fingers to move, much less adequately stretch my tight pucker. I realize I'm running perilously low on time, which I have no doubt was Derek's intention.

With no other option, I lather the plug with lube. I stand up at the end of the bed, spread my legs, and position it against my hole, reasoning that it might be best to let gravity do most of the work. At the last second, I bunch up the hem of my shirt in my mouth to bite on. Then I sit down and impale myself on the dildo.

My scream is muffled by the shirt, but it does nothing to dull the sharp, excruciating pain that rips through my ass and gut. Despite having seen for myself the plug's exact size, I swear it feels a foot longer and thicker than it really is. I'm swallowing down sobs, and it hurts so bad I can barely stand back up, but I'm not finished yet. I angle the laptop screen toward the bed and pull up the camera options. I set a timer to snap a photo, then crawl onto the bed, my plugged, throbbing ass in the air.

There's a shutter snap sound effect, and I quickly drag the saved picture into the chat box. Not a moment too soon. The last minute ends just as I hit send. I wait breathlessly, tears streaming down my cheeks. I know better than to remove the plug yet.

Good boy.

I suck in a breath as warmth suffuses me. Even an ocean away and through a computer screen, Derek Harrow still has me hanging on his approval. Pitiful.

Three little dots show he's typing again.

Get back on the bed but face the screen. The camera is live.

I notice a little red light blinking next to the lens. Good thing I didn't pull out the plug. I crawl back onto the bed and wait on all fours, staring at the screen. My ass is still burning and throbbing around the plug, but my mind feels curiously far away. Like I'm outside myself, watching all this happen.

That doesn't last long.

The plug starts vibrating. That's nothing new. I'm so used to it, I barely notice. But then the dildo jumps inside of me—no it thrusts. I grunt and fall onto my face, scrambling to make sense of what's happening in my ass. Not only is the plug thrusting slowly into me, like someone is fucking me with it, but I swear it's getting...bigger.

Through my bewildered haze, I register the sound of another message alert. I blink to clear my bleary vision and squint at the screen.

Hands and knees. I want to see your face, slut.

Somehow I manage to get back on all fours. I keep my face up, but I can't focus on the screen or anything other than the rhythmic violation happening in my ass. The dildo thrusts repeatedly, while the head expands and deflates at varying intervals. My channel is on fire, and I want nothing more than to rip out the plug. I grip my blankets in my fists to keep them still.

As I slowly begin to pick out a pattern in the dildo's pumping, I realize I'm rocking my hips in conjunction with it. If I get the angle and timing just right, the plug massages directly against my prostate. Pleasure ripples through me, drowning out the pain. My cock is getting hard, and I'm moaning like a whore.

Ping.

I knew you would like it.

I bite my lip and shake my head no, but my denial means nothing while I'm busy groaning and humping the air.

Do you wish it was my cock raping your little boy pussy?

My cock twitches violently, and I gasp. I can't bring myself to answer, but I can't bring myself to shake my head no either. That's not good enough for him.

Say it.

I moan helplessly, rutting my hips like a frantic dog. My mind is a tight, pulsating coil of pain and pleasure and humiliation.

Say it, and I'll let you come.

"I wish it was your cock inside me." The words tumble out of me in a rush. My brain might be stubborn, but my body is desperate for release. "Please let me come, Mr. Harrow. Please."

I'm too far gone. If he says no, I'm not going to be able to stop and god only knows what punishment will await me then. Instead of killing my arousal, the phantom memory of his belt raising welts on my ass sends another surge of need directly into my balls.

You can't touch yourself, but you can come.

The directive doesn't slow me down in the least. I pump my hips into the empty air, relishing the brutal precision of the plug in my ass as it fucks me toward my climax. I cry out and jettison spunk all over my own bed. Even when I'm dry, I keep bucking my pelvis, wringing out every last vestige of bliss from the orgasm.

For a long while, the chat window is silent. There is only the persistent blinking of the tiny red light to tell me that Derek is still there. Is he jerking off right now? The thought of my punctilious and perfectly controlled boss masturbating to my pathetic, horny performance fills me with a strange sense of pride.

At long last, another message.

What are you?

"Your little cockslut," I say.

Good boy.

The light dies and the screen goes dark. A few seconds later, the butt plug goes still. After a long, nervous minute of waiting, I finally reach back and pull it out slowly. My channel is so tender and sore that it almost hurts worse than when it went in. I climb shakily off the bed and tap a few keys on the laptop. It works fine, but the pictures, video files, and chat message history have all been wiped clean. As if it never happened at all.

After that, my dream of two weeks of freedom evaporates pretty quickly. When I'm at home, the laptop with its blinking red light is my taskmaster. Pretty soon I can't even look at my bed without thinking of Derek Harrow and all the ways he's turned me into a sobbing, needy mess with only words on a screen. I'm sure that was his intention.

At work, though business-related correspondence comes through my email as usual, I also receive texts from a blocked number that ensure I never forget for a moment who's pulling my strings. One morning, he makes me bend over the sofa in his office and fuck myself with a dildo until I come—and then I have to clean up the mess I made using only my tongue. Another evening, he has me stark naked and kneeling on top of his desk, blindfolded with a plug in my ass. I must stay there motionless, hands clasped behind my neck, for an hour. It's after-hours and everyone knows he's out of the office, so the chances of anyone coming across me are slim—but that doesn't make me feel any better when he refuses to let me lock the door.

Despite all this, I'm determined to make the most of his absence. Since I have access to his day planner online, I know that he has an early morning meeting on Friday before his return flight, so I figure with London being six hours ahead, I'm safe to ask Penny on a date for Thursday night. Nothing too fancy. We're just going for dinner and drinks, but I'm so excited I spend the day counting down the minutes.

We plan on going right after work, so when I receive a text at 4:50 p.m. I assume it's her. Then I look at my phone and my heart sinks. Blocked number.

I want you naked and plugged on your bed in exactly one hour.

Fuck, fuck, fuck. Doesn't he ever take a night off? Do British hotels not have pay-per-view pornos? He's a drop-dead gorgeous multi-millionaire; it can't be that difficult for him to find someone to help him get his rocks off, even in a foreign country.

I look up to see Penny coming across the office, stunning in an understated green dress and heels. Derek Harrow can fuck himself for all I care.

I can't tonight, I text back quickly. I have important dinner plans.

I grab my coat, and Penny and I are in the elevator when I receive his reply.

It was not a request, Jack.

"Everything okay?" Penny asks, noticing my expression.

"Yeah, no worries." I force my fingers to remain steady as I type my response.

Sorry, I can't.

When the elevator reaches the lobby and the doors ding open, my phone dings again.

Then I hope it's worth the price you'll be paying.

A sense of dread creeps over me, but I refuse to be cowed. It's much easier to be brave when he's not looming over me, gray eyes boring into my soul. I set my phone to silent and tuck it away. I'm going to have a good time tonight if it kills me.

When the next morning comes, I steel myself for word from Derek, but the chat window on the laptop is silent, and there are no messages on my phone. After his meeting he has an eight-hour return flight, so maybe that will give him time to cool off. Besides, it's not like I haven't survived plenty of his punishments before. And the dinner with Penny was definitely worth it. She kissed me after, and we set a second date for next week.