Upward Ambition Ch. 01

"Please," I manage, in a cross between a hiccup and a sob. "Please let me come, Mr. Harrow."

I feel his cock jump at that, and I'm perversely pleased with myself. Which is ridiculous. It's not like I have anything to be proud of, bent over a desk, crying and begging to come while another man handles my junk.

"I don't think so," says Derek. "You haven't earned it yet."

He steps back, and at the sudden loss of his weight, I find myself so off balance that I nearly collapse. I'm so fucking close. I know if I stroke myself even once, I'll come like a geyser. But the thought of more punishment keeps me in position, legs spread, forearms planted, palms down on the desk. Derek hasn't told me I can move yet.

He strolls around the desk and sinks into his chair, the picture of relaxation.

"Look at me," he says. Trembling, I raise my head. As I meet his eyes, I'm achingly aware of the hot tears drying on my cheeks. He's still wearing that smirk, and scalding humiliation washes down my back. Derek leans back in his chair. "Get on your hands and knees and come here."

My cock twitches. I barely have time to register what's happening before my knees hit the ground. After a month of following Derek's orders, it seems my brain has gotten stuck in a pattern of obedience. At least I hope so. The alternative is that I'm genuinely getting off on all this, and I'm not sure I can stand the thought of that.

I crawl around the desk. The movement sends ripples of discomfort across my buttocks. Even through my trousers and boxers, I'm certain there are going to be bruises. When I reach Derek's feet, I stop and kneel up, but he grabs my tie and yanks me forward, until I'm trapped between his legs.

The bulge in his pants is inches away from my face. I try to lean away, but his grip on my tie is unyielding. He slides his free hand around the back of my head. With his fingers twining in my hair, he jerks my head back so that I have no choice but to look him in the face. His bright grey eyes bore into mine.

"You ever suck cock before?" he asks, his voice much less smooth than it was before. His pupils are blown wide with arousal.

With his grip on me, I can't shake my head. I'm quivering all over as I lick my dry lips. His nostrils flare as he watches me.

"N-no," I manage.

"That's a shame." He releases my tie and rams two fingers into my mouth. I sputter, my instinct being to bite down, but his cruel grip on my hair reminds me that might not be the best idea. "You've got a mouth made to be stuffed with cock. But I don't mind being your first."

His words heat my blood as his fingers invade my mouth. He seems amused by my wide-eyed bewilderment that this is happening to me. That I'm kneeling here and letting it happen. I know I could push him off and run for the door, but something about his grip and his gaze keeps me pinned to the spot. Helpless to save myself.

"You're a little slut, aren't you," he says, with a low laugh. He removes his fingers, which are slick with my spit, then reaches down to circle them around my penis. "Look how hard you are, just from a whipping and the thought of sucking me off."

He pumps his hand once, twice. I groan, trying to pull away from him even as my hips move of their own accord, desperate for a release. He keeps me firmly in place and slaps me across the cheek.

"I haven't given you permission to come yet, little slut."

I blink at him, lost in a haze of arousal. He slaps me again, harder, and I come back to my senses. Barely. My cheek is stinging, and more tears are building in my eyes. I just want to crawl away. I just want to curl up in a ball and weep. I just want to come.

"Please," I beg, tears streaming down my face. I'm a fucking mess. "Please."

"I told you," he says, wiping his fingers on my shirt. "You have to earn it first."

I'm so beyond dignity at this point. I hesitate for only a second before I start undoing his trousers. I free his penis, which is fully erect and impressive both in length and girth. I lean forward. I can't believe I'm about to do this.

Derek jerks my head back, and I gasp in surprise. My gaze flicks questioningly from his bulging member to his eyes.

"Good sluts ask nicely for the privilege of cock," he says, with a mirthless smile. "Are you a good slut, Jack?"

My eyes trail downward again. I don't want to wrap my lips around that bulbous head. I don't want him ramming that length down my throat. I don't want any of this. But I have a feeling that doesn't matter anymore. I'm here, on my knees in front of Derek Harrow, and it's my job to give him whatever he wants.

"Please, Mr. Harrow," I say. A tremor runs through my voice as I meet his commanding gaze again. "May I suck your cock?"

His smile widens, and he relaxes back in his chair. He drops his hand from the back of my head.

"Go ahead then. Let's see if that mouth of yours is as useful as it is pretty."

I swallow hard. Somehow this was so much easier when he was holding my head. Now as I bend forward, I know with every painstaking inch I'm doing it of my own volition. My lips gently brush the reddish-purple head of his penis, and I realize with a sudden rush of panic that I don't know what the fuck I'm doing. I had a girlfriend once who didn't mind sucking me off, but it never occurred to me that I should be taking notes.

Hesitantly, I stick out my tongue. I can feel the slit and taste the salty pre-cum. It doesn't taste as bad as I expected, and I give a few more experimental licks. I settle in and try licking a long stripe along the underside. Judging from the slight groan Derek emits, that's a winner. I do it one more time, and then return my focus to the head. Carefully, I wrap my lips around it and start to suckle like a babe on a tit. It's velvety smooth except for the bumps of the veins that wind around it. My efforts seem to be working, and I keep sucking, thinking that if I can get him off like this, I won't have to attempt to go down any further on his massive cock.

But Derek has other plans. He grabs my hair again and pulls me off. With his other hand, he lifts up his penis.

"Now my balls," he says. His breathing has quickened noticeably. "And watch those teeth."

I wet my lips again as he guides my face toward his sac until my nose is buried in his pubic hair. I breathe in his musky, masculine scent as I slowly tongue his huge, heavy balls, first one and then the other.

"Mouth them."

I comply, although I can barely fit one at a time in my mouth. I suckle on them more gently than I did the head, doing my best to keep my teeth from scraping.

"You like that, don't you," he says, stroking the back of my head like I'm a prized pet. Without thinking, I let out a low, anxious whine that I suppose could be construed as a yes. "That's a good cockslut."

I keep suckling until Derek decides he's ready for the main event and pulls me back. Before I can protest, he feeds his length into my mouth. My jaw aches as I try to accommodate his girth. I try to work my tongue around it, sensing that's what I'm supposed to do, but there's not much room to maneuver. Then the head of his cock hits the back of my throat. I gag and try to pull off, but Derek holds me still. As the air vacates my lungs, I plant my hands on his thighs and push. He only wraps my tie around his hand and yanks me back into place.

I gag continually as he rams himself down my throat. His balls slap against my chin, and I realize he's fully seated in my mouth.

"Shhh," he says soothingly, as if he isn't currently choking me on his dick. "You have no idea how pretty you look with your lips stretched around my cock. You're such a good boy, Jack. My perfect cock whore."

The filthy praise settles on me like a warm blanket, even as my throat convulses. From the expression on Derek's face, he likes that a lot. He holds me steady for another thirty seconds, studying my face with ravenous hunger as I choke and wheeze. By this point, my face is a mess of snot and tears. I know I must look disgusting, but if anything it seems to turn him on more. At last, he pulls back until only the head is in my mouth. I cough and sob, trying to suck in as much breath around it as I can. Before I've even remotely recovered, he holds the sides of my head in an iron grip and slams back down to the hilt. There's nothing I can do but kneel there and take it as he face-fucks me into oblivion. Black spots dance in my vision, and my fingernails dig into his thighs in an attempt to keep myself from passing out.

At last, I can tell he's close to orgasm when his thrusts grow shorter and more erratic.

"You're going to swallow every last drop," he says in a guttural voice. "Do you hear me, slut?"

Of course I can't reply, and a couple seconds later his spunk is shooting down my throat and filling my mouth. I swallow the salty warmth as best I can. It feels like it goes on forever, but finally I gulp down the last of it. He leaves his softening member in my mouth and rests one hand on my head as he slumps back in his chair with a satisfied sigh. I'm sobbing from the overwhelming sensations, but still I continue to suckle my boss's limp cock while he idly pets my hair.

It's several minutes before he finally pushes me back gently. I sit back on my heels—the pain from my whipping is the last thing on my mind right now—and gasp in short breaths. I swipe my sleeve across my face in an effort to clean away some of the snot and tears. Derek regards me with heavy-lidded eyes, his fingers tapping an absent rhythm on the armrests.

"You may jerk yourself off now," he says.

My stomach twists. In my hazy desire for orgasm, it didn't occurred to me that achieving it might be merely another show for Derek's pleasure. I'm not even sure I can get off with another man watching. As I tentatively wrap my hand around the base of my penis, I realize immediately that, no, another man watching isn't going to be an issue. Or maybe it's just this man in particular.

I start to stroke myself, wondering at the fact that I've kept my hard-on this entire time. My own dick isn't nearly as impressive as Derek's. As in my job and every other aspect of my life, I'm aggressively average.

"Keep looking at me," Derek snaps, when my eyes drop down to my lap. I meet his gaze, flushing with humiliation as I continue to work my own cock. I spread my legs a little wider and use my other hand to fondle my ball sac the way he did. Pleasure is building up rapidly inside of me, like a dam ready to burst. Derek's eyes are glazed with lust, and I realize his own member is hardening again.

"Thank me for punishing you and letting you taste my cock," he says, touching himself.

"Thank you for punishing me," I gasp out, as I pump myself faster and faster. "And for letting me taste your cock."

"Are you my little cockslut?"

"Yes." My whole body throbs with the need for release. I'm so fucking close.

"Yes what?"

"I'm your little cockslut." I climax with those words, spewing all over myself. I slump over, every muscle quivering, defeated by my own pleasure. Tears are still pouring down my face, but now I'm not sure if they're from shame or relief.

"You've made a mess," says Derek. I raise my head to look at him. He's still fingering his cock, but not with any real sense of urgency. He seems utterly at his leisure. "Clean yourself up."

It takes me a few moments to understand what he means. I kneel up again, shocked by my own obsequiousness as I start to lick my own cum off my hand. Something like misery wraps around me as the rational part of my brain looks on in horror, helpless to stop my slavish sucking of my own spunk-covered fingers. When my hand is clean, Derek gestures wordlessly to the floor. I look down to find a few wet stains on the thin carpet. With a hiccupping sob, I bend down and keep licking, tasting nothing but carpet fibers and the faint hint of salt until finally the damp spots are more saliva than semen.

I'm trembling when I straighten back up. I can't bring myself to look at my boss. The true measure of my humiliation has finally begun to settle in, and every inch of me is aflame.

Derek stands and tucks himself back in. He zips up his pants, replaces his belt, and smooths a hand through his hair. Just like that, he's back to his impeccable state. He walks past me, patting my head as he goes.

"You may go," he tells me. "I'm glad we were able to come to an understanding."

An understanding?

With agonizing effort, I manage to make it to my feet. My knees are so weak, I have to lean against the desk while I arrange my clothes. My pants and shirt are both splattered with my pale, sticky semen. I'll have to button up my coat and keep my shoulder bag across my thighs when I leave the building. Thank god my cubicle is right next to Derek's office.

I trudge toward the door, my eyes downcast.

"Oh, and Jack?" says Derek, as I open it.

I steel myself and turn to look at him. He's sitting again on the edge of his desk, where not too long ago I'd bent over while he belted me. Fuck, I'm never going to be able to come into this office again without remembering this night, am I? Is that what he wanted all along?

"Yes sir?" I ask, with forced lightness.

"Be here an hour early tomorrow. I think I'll have use for you again." His eyes spark with a wicked glint as his lips curve into a predatory smile.

"Yes sir." My voice is barely a whisper now. I leave, pulling the door shut behind me. Maybe I should have gone with Plan B after all.