Upward Ambition Ch. 02

"Looks like you're late for work." He saunters behind his desk and sinks into his chair, the picture of leisure. He meets my gaze without a trace of irony. "I suggest you get dressed and get out of here. I'd hate to have to add tardiness to your disciplinary file."

"But—"

"But what, Jack?" He stares back at me, utterly unmoved. Cold, cold bastard.

I swallow and push myself upright. My knees quiver, but don't buckle.

"Nothing, sir." I retrieve my underwear and pants. I suppose I should be grateful that he's letting me get dressed before kicking me out. I try in vain to ignore my bruised backside, the aching of my hard cock, and the foreign object still rammed up my ass. It's going to be a long day.

"Don't forget the expense report," Derek says mildly, as I'm on my way out the door.

"I won't, sir," I manage through gritted teeth. I head back to my cubicle. Walking with the plug is just as uncomfortable as I'd suspected it would be. I gulp down more water, then pick up a random file to use as a shield over my crotch as I waddle to the restroom. It's early yet, so there aren't very many people around, and thankfully they all still seem half-asleep.

In the men's restroom, I splash cold water over my face, trying desperately to marshal my senses. My cock is still begging me for release. At least that's something I can handle, now that I'm alone. I lock myself in a stall, but before I can get down to business, my phone buzzes in my pocket. It's a message from—who else—Derek Harrow.

If you come without permission, you will not like the consequences.

Motherfucker, how did he know.

I press my forehead against the stall door, almost crying with the frustration. But no matter how hard I try to convince myself that there's no way he could know if I jerked myself off right now, I can't do it. Ironically, the thought of his immense displeasure helps to dampen my arousal, at least a little bit. I wash my face again and take a few minutes to straighten myself out, until at last I just look like someone who's running on too little sleep, rather than someone who's spent the past hour having his ass spanked and stuffed by his boss.

By the time I organize the expense report and head to accounting, I'm no longer erect, and I've even gotten marginally more used to the plug. Enough that I can walk with some degree of normalcy.

Penny is at her desk, cute as always in a baby blue dress with a white cardigan. Her hair is up in a messy bun, with loose tendrils nicely framing her face.

"Hi, Jack," she says with a grin. "You're just in time."

"I live to serve." My voice is only a little stilted as I hand her the report. I do my best to match her smile. Just the sight of her makes me feel more like myself again, and the last thing I want to do is go back to my cubicle, where only a wall separates me from Derek. I lean my hand casually on her desk. "Got any fun plans this weekend?"

"Plans, yes. Fun, no. My friend is moving across town, and I promised her I'd help."

"Maybe we can—" I'm cut off as my lungs suddenly shrivel in my chest. The butt plug is vibrating. It's a good thing I already have a hand on Penny's desk to steady myself, because otherwise I'm pretty sure my knees would've given out.

"Are you okay?" Penny asks, alarmed.

Oh god, can she hear it? Surely not. Panic lances through me. Somehow I manage to convince my hands to grip my head instead of my ass.

"Yeah, just a sudden headache," I manage. "I should get some Tylenol or something."

I stagger away before she can reply. The buzzing inside me intensifies. Fuck, fuck, fuck.

I don't even remember the walk to my cubicle, but somehow I make it there. My whole body is reverberating, and even worse, I'm feeling phantom echoes of the pleasure I'd felt when Derek massaged my prostate. My cock is stirring.

I've barely reached my desk when my phone rings. I answer it automatically.

"There you are," says Derek's voice in my ear. "I need the Deepwell contract. Legal should have given it to you yesterday."

He hangs up before I can reply. The plug has stopped vibrating, and I'm able to catch my breath. I grab the contract from my inbox and go into his office. He's not alone. Jeremy from sales and Kevin Grant, the CFO, are seated in the armchairs across from his desk. They're chatting about baseball when I enter and don't pay me any mind. Jeremy and I started here about the same time, but he's worked his way to head of sales while I'm still delivering contracts and making coffee runs. I don't look at him.

"Hold on," Derek says, as I hand him the contract. He starts digging around in his desk drawer. "I have something for you."

The plug starts vibrating again. I choke on my own spit but manage not to react beyond that. In my periphery, I can tell Jeremy and Kevin are both looking at me curiously now. I keep my eyes on Derek.

"Hmm," he says, closing the drawer. "I must have already given it to you."

He meets my gaze with a smile that is pure, unadulterated smugness.

I hate you, I hate you, I hate you.

"Okay." My voice cracks slightly, and I clear my throat. "Let me know if you need anything else."

"I will," says Derek, leaning back comfortably in his chair and crossing his legs. "Shut the door on your way out."

I obey. It's another ten minutes before the buzzing stops again, and by then my cock is weeping pre-cum and I've taken to stabbing myself in the thigh with a paperclip to distract myself. The day passes at an agonizing pace. I'm not sure I manage to get any work done, besides answering the phone when it rings. And of course delivering no less than ten different contracts and reports to Derek next door—all of which could have been emailed. He seemed to enjoy watching me squirm, and—on those occasions when he didn't turn on the vibrator—watching me hover in dreadful anticipation of it.

By the time the end of the day arrives, I'm a throbbing wreck. I'm fairly certain that even a passing breeze on my crotch would have me coming like a geyser. I'm just closing out my email and locking my computer when my phone rings. Derek.

"Get in here," he says, and hangs up. Always the charmer.

I go into his office. It's empty except for Derek. He's in the process of shrugging off his suit jacket and loosening his tie.

"Shut the door and lock it," he says, without looking at me. He drops onto his sofa, in much the same attitude as I'd first found him this morning.

I lock the door, not sure if I should take that for a good sign or bad. I turn back to face him. He's watching me now, with ravenous eyes in an otherwise empty expression.

"Would you like to come, slut?" he asks in a mild tone.

I quiver at the words.

"Yes sir."

"Then get over here and earn it."

I don't even hesitate. I cross the room and drop to my knees in front of him. He catches my chin in his fingers and tilts it up until I meet his eye.

"You've wasted enough of my time today," he says, unsmiling. "I'll give you until the end of the workday to earn your orgasm. Otherwise, there will be consequences."

I glance at the clock. It's 4:53 p.m.. Seven minutes left.

He drops my chin, and I lunge forward to undo his belt and trousers. I free his cock and lean forward, but he grabs my hair and yanks me painfully short.

"Aren't you forgetting something?"

Delirious as I am with anticipation of him once again filling my mouth, as well as my own urgent need, it takes me a few seconds to realize what he means. Good sluts ask nicely for the privilege of cock.

"Mr. Harrow, may I please suck your cock?"

His lips curl into a smile that's equal parts cruel and satisfied. He releases my head and leans back.

"Six minutes," he says.

I dive forward like an eager whore. He's only semi-erect, which seems unfair, but it's not like I can complain. I move first to his balls, licking and sucking (and careful of my teeth) until his penis is fully hard. I lick the entire length of it, taking note of the soft groan he emits as I do so. I wrap my lips around the bulbous head and start to suckle it, working with my tongue as best I can. Then I lick the underside of the shaft again.

I'm conscious of minutes ticking by, and my pace grows more frenzied. I lap at his sac like a thirsty dog, then use my hand to continue fondling his balls, while I cover his shaft in hot, sucking kisses. Even as I worship his cock with devotion and desperation, I know it's not enough.

It would be so much easier if he would grab my head like he had the night before and ram his cock down my throat himself. But I know he's not going to make it easy for me. I'm running out of time.

I plant my hands on his thighs, bracing myself as I go down on him. My first attempt is aborted prematurely by my accursed gag reflex, but I recover quickly and try again. This time I manage to get most of him in my mouth, even as my throat spasms and tears flood my eyes. I force myself up and down as fast as I can, though it's nowhere near the jackhammer rhythm he used last time. It's not long before I'm a gagging mess again, swallowing repeatedly to ease his passage and hoping that the stimulation is enough to get him off, because he's too big for me to make use of my tongue. How much time is left?

I can feel the strain in his muscles where I grip his thighs. I realize that his chest is heaving with quickened breaths. So close. I go down as far as I can, so that my nose is almost buried in his dark pubic hair, and raise my eyes. Our gazes lock. My vision is blurred by tears, but I don't look away. I keep sucking. A sound like a whimper escapes me.

That's when he grabs my head, slams me to the hilt, and shoots his load down my throat. I gulp down the cum, trying not to gag. I don't know what would happen if I heaved his own cum back into his lap, but I know that I definitely don't want to find out. At last he pulls out. Some semen spills onto my lips and dribbles down my chin. I wipe it with my hand and suck it off my fingers while he watches, his pupils blown so wide that his eyes are nearly black.

I look at the clock. 4:59 p.m..

Wordlessly, he pulls me up and maneuvers me back over his lap. I'm tense all over, waiting for a blow to land, but he only rubs my back in long, gentling strokes. He shifts me forward enough to undo my trousers and slip out my cock. I'm almost crying with relief by the time he wraps his fingers around it and begins to pump it slowly.

"What are you?"

My head is so hazy with desire and need, I can barely make sense of what he's saying. Suddenly the butt plug begins to vibrate again, much stronger than before. I gulp for air as he strokes me faster. The heel of his other hand presses against the base of the plug, grinding it deeper into my ass. He moves it around until it hits my prostate and I writhe against him in pleasure.

"What are you?" he demands again.

"I'm your cockslut," I gasp out.

With only a few more pumps, he brings me expertly to orgasm. I'm alight with ecstasy as I spurt into his hand, and the bliss is so complete that I don't protest when he brings his sticky fingers to my mouth.

"My good little cockslut," he says, petting the back of my head as I suck my own spunk off his hand.

I hate him so much, but I'm so beyond caring.