Upward Ambition Ch. 10

(Author's note: Hello, I'm still here! I wish I could promise to be speedier with these updates, but time flies when you're working two jobs, unfortunately. I will say that I am determined to finish this story...eventually. Along with my usual note that what follows is fantasy and you shouldn't base any real-life sexual encounters on anything you read here, I also want to note that this chapter falls back more squarely into "non-con" territory. So if that's not your thing, you should give this a miss.)

I manage to drag myself out of the shower and dry off. I desperately want to rinse out my mouth with mouthwash, but I have a feeling that Derek wouldn't approve of me ridding myself of the taste of his spunk so soon. He'd probably deposit another load on my tongue, just to make a point.

When I leave the bathroom, I find the clothes I was stripped of the night before folded neatly on the foot of the bed, along with my shoes, wallet, and keys. Courtesy of Groves no doubt. Based on how he reacted to finding me in Derek's bed, knowing I was in his shower probably made the old butler apoplectic.

I get dressed quickly. It's a relief to feel like a normal human again.

Derek emerges from the closet, sleek as always in all black. He gives me a cool once-over as he secures his second cufflink. He is clearly unimpressed, which seems unfair. There's not a single person in the entire company who would pass muster next to him. Especially considering one of his suits probably costs more than most employees make in a month.

"Come here," he says, before disappearing back into the closet.

I steel myself and follow him, not sure what to expect. He pulls open a drawer in the bureau, revealing rows of rolled neckties, each in their own little cubby. Jesus, is there any part of his life that's not meticulously, painstakingly organized?

Derek peruses for a while before selecting a silk tie the color of dark chocolate and handing it to me. Admittedly it complements my pale green shirt perfectly, but the thought of being responsible for one of his ridiculously overpriced designer neckties makes me feel a little sick to my stomach. I know better than to think that I have a say in the matter. I slide it under my collar, and even though my hands are shaking slightly, I manage to make a respectable knot.

I guess Derek disagrees, because I haven't even tightened it all the way before he grabs it and pulls it loose again.

"For fuck's sake," he mutters. He jerks me closer and starts tying a much more elaborate knot than I've ever managed before.

"Are you really firing Kevin today?" I ask, trying to distract myself both from how useless I feel and how near he suddenly is. My cheeks are warming up. Goddammit, why am I reacting like a hormonal teenager? Literally ten minutes ago he was choking me ruthlessly on his cock.

His lips twitch in an almost-smile.

"I finally figured out what he was holding over my father. Some overseas tax fraud bullshit that my father was neck deep in. My attorneys made a deal with the government and negotiated a very reasonable payment plan for the back taxes. The paperwork went through this morning. Grant doesn't have any leverage left. I even found a loophole in his contract that will let me fire him without severance. He's done."

He adjusts the necktie until it's snug against the hollow of my throat.

"What about everything else?" I ask.

"Everything else?"

"He saw us last night at the party. Aren't you afraid he'll tell someone?"

Derek chuckles. He hasn't yet released the tie.

"He knows better than to talk about anything that happens at one of Gina's events. She makes everyone sign their lives away in non-disclosure agreements."

"Oh," I say, then something occurs to me. "I didn't sign anything."

"Yes, you did. It was in the packet with the new employment agreement you signed."

I vaguely remember receiving the documents on Derek's first official day as CEO. He told me it was just a renewal of my old agreement, and nothing had changed. I skimmed the first paragraph or so and then signed on all the dotted lines. There were a lot of pages. I have no doubt that one of them was indeed an NDA barring me from spilling the secrets of any sex parties hosted by the city's elite. Probably on pain of death.

But that also means that Derek knew from his very first day as my boss that he was going to take me to one of those events. The thought is simultaneously terrifying and strangely flattering. I recall that first night in his office, when all of this started. He told me that he'd known from the moment he met me that it wouldn't be long before he had me bent over his desk.

The fact that I am now more flattered than disturbed is disturbing in itself.

"You should really read contracts before you sign them, Jack," he says with a hint of amusement.

"How stupid of me to trust my boss."

He makes a noncommittal sound. His gaze has zeroed in on my neck, and he leans in to tongue my pulse point. A small moan escapes me, which only encourages him. His grip tightens, twisting the tie until it constricts my windpipe. Great, more breath play.

His lips attack my neck with more vigor. It takes me a couple seconds to realize that he's purposefully giving me a hickey, too high to be covered by my collar. Fucking hell.

I squirm under his mouth, but it's not like I can go anywhere. Suddenly his palm is pressed firmly against my crotch. I would suck in a sharp breath if I was able. My heart pounds against my chest so hard that I'm sure Derek can hear it. The blood stirs in my groin at his touch, but he doesn't move--not to press harder or to pull away.

The suction on my neck is almost painful now. It's definitely going to bruise. The guys in sales will never let me live this down. Derek loosens his grip just enough for me to fill my lungs. The oxygen is a rush of euphoria that makes me feel light all over. My testicles are growing tight, and I realize I'm grinding against Derek's hand. Fuck, how long have I been doing that? I tell myself to stop, but he's restricted my airflow again, and I'm hazy with arousal and lack of oxygen, and it feels so damn good.

His lips break from my neck with a small pop, and he leans in even closer, until his breath tickles my ear.

"After I fire Grant," he whispers, "I'm going to bend you over his desk and fuck you until you see stars."

I would moan if I had any air left in my lungs. My hips snap forward, and the friction of his palm on my dick feels deliriously good. I'm only partially erect, but I know it won't take much to get me all the way there.

When Derek releases the chokehold, I gasp in a deep breath, and the flood of endorphins weakens my knees. Derek ignores my wobbling and draws back to admire his work. He traces the thumb of his free hand around my new hickey. I wince at the sting.

"Incorrigible little slut," he murmurs. He gives my package a quick squeeze, and then, to my chagrin, pulls away completely. "I've got something to help with that."

He goes to the other end of the enormous closet and retrieves a small box from a different chest of drawers. He pulls out a series of silver rings connected by a central strip of black leather. My stomach drops while my balls tighten reflexively. Derek places a hand on the center of my chest and pushes me against the wall. He sets the device on top of the bureau next to my head, like some kind of threat, though I suspect that my fate is inevitable regardless of what I do.

He unbuttons my pants and tugs the zipper down. His palm is still pressed against my chest, where surely he can feel my pounding heart. He pulls my pants and underwear down enough to free my cock and balls. I close my eyes and try not to think about the spicy, familiar scent of his cologne or the feel of his warm breath against the hickey on my neck.

"Touch yourself," he commands. The words have barely left his mouth before I grab my shaft and start stroking. I know he probably wants me to bring myself to the edge just so he can deny me, but right now I don't care.

He tongues the bruise on my neck while I jack off slowly, trying to savor it while I can.

"Hurry up and finish," he says, and a jolt of excitement shoots through me at the realization that I actually get to come. I quicken my efforts before he can change his mind. "And if you make a mess on my floor, you're going to lick up every drop."

I moan. The threat doesn't do anything to dampen my arousal--if anything, it only drives me closer to the edge. My shaft is slick with pre-cum, easing the passage of my hand. Even with total control over my grip and speed, it's not as good as I was expecting--not as good as his mouth, I realize. Oh god, he has completely ruined me. His words from only a couple days ago (it feels like a couple years) come back to me. "By the time I'm through, you won't be able to find your pleasure anywhere else."

Maybe I am already that far gone. And he isn't even through with me yet.

A sound tinged with desolation escapes me, and he goes still, as if he sensed the moment my desire tipped into despair. His breath is cool now against the saliva-damp hickey, and his gaze shifts down to my member, which is suddenly wilting despite my ministrations. I hate how attuned he is to my body, and how attuned my body is to him. His hand wraps around the back of my neck, and something about that helps me breathe easier. When I focus less on my own hand and more on his punishing grip, on the diamond glint in his eyes and the way he worries my bottom lip between his teeth, blood rushes again to my cock.

"This is taking too long," he murmurs into my mouth. "Come, slut. Now."

No one is more surprised than me when I erupt on command, barely managing to catch my sperm in my other hand. Derek has never once betrayed a hint of doubt that I will obey his every order, but I swear even he is surprised by my promptness, considering only seconds ago I was going soft.

"Good boy." His uncharacteristically pleased tone sends a jolt of delayed satisfaction straight to my groin. He grabs my wrist and lifts my spunk-filled hand toward my mouth, and I'm too blissed out to even hesitate as I lap up my own cum. Better than the floor, right?

He releases my neck, and I waver, leaning most of my weight against the wall. He retrieves the metal and leather device from the bureau. Fuck, I'd forgotten about that.

I already have my suspicions of what's in store, but I still wince when he starts to feed my limp manhood through the rings. The largest one ("large" being a relative term here) fits snugly around my scrotum and the root of my shaft, the cold metal kissing my perineum. The rings are increasingly smaller and tighter against my shaft, with the final one flush beneath the head. It's the first time Derek has put a chastity device on me, but I have a feeling this one isn't for beginners. Shocker.

It's uncomfortable, but not painful, at least until he starts fondling my balls. I squirm, oversensitive from my recent orgasm, and he slots his hand over my throat again, applying pressure at the pulse point until my mind goes fuzzy. I'm hopeful that he won't be able to arouse me again so soon, but my traitorous prick has other ideas, as always. It's not long before my aching member is swollen against the confines of the rings, and--pain whore that I am--the ruthless constriction only makes me harder, a feedback loop of pleasure and torment.

I squeeze my hands into tight fists at my sides, trying to remain silent while he amuses himself with my forced chastity.

"I thought we were in a hurry," I manage through gritted teeth.

"We are." Derek gives my tight balls a little slap that makes me yelp and then straightens my tie. "And that's why I'm going to wait until later to punish you for being a smartass."

He grabs his watch from the top of the bureau and leaves the closet. I stare at the doorway for a few seconds before my mind catches up with me. I stuff myself back into my trousers and hurry after him before I can incur even more punishment.

#

In the city, Derek has his driver drop me off at the coffee shop a couple blocks away from the office. I order our usual and emerge from the shop to find that I've been left behind. No surprise there. I hoof it the rest of the way to the office as fast as I can, because I know from experience that if I deliver lukewarm coffee, Derek will just make me go back for another one. Nuking it in a microwave is not good enough for him.

I'm sweating when I arrive, but the coffee is still hot, and I've managed not to spill any on myself--or more importantly, on Derek's tie. My hard-on has lessened slightly, though not all the way, thanks to the ring around my balls. I'm able to mostly ignore it, except for the occasional pause to adjust myself when no one is looking. If there's anything my time with Derek has taught me, it's how to work through any amount of discomfort.

Derek is on the phone in his office. He's relaxed in his chair, tapping a pen absently on the desk while he discusses annual metrics. He completely ignores me when I place his cup in front of him. His ability to compartmentalize is truly astounding.

When I get back to my cubicle, Penny is waiting for me. My ass stings at the sight of her, like a Pavlovian response. I haven't forgotten that it was flirting with her yesterday that pissed Derek off and sparked last night's chain of events.

"Hey," I say as I sit down gingerly. I try to sound friendly but also busy. "How's it going?"

"Hi," she replies. She's fidgeting with the last button on her cardigan. "Good, how are you?"

"Good." So far there's nothing flirtatious about this riveting conversation, so hopefully I can avoid a recurrence of Derek's wrath. "Sorry, I've got a lot to catch up on this morning."

"Okay, can we just talk really quick though? It will only take a second."

"Sure." I take a sip of my coffee, just to have something to do with my hands. I should never have gone on a date with her in the first place. And I definitely shouldn't have kissed her and then set another date for Friday. Breaking it off is going to be so awkward.

She fumbles a little more with the button.

"So, um, I got promoted to Director of Accounting."

"That's amazing," I say. "Congratulations!"

"Thanks." She smiles and pushes a lock of hair behind her ear. Fuck, why does she have to be so gorgeous? "I wasn't expecting it at all. When Derek told me last night, I honestly thought he'd gotten me confused with someone else."

"Derek?" I echoed.

"Yeah. It was crazy. I didn't know the CEO got involved in that kind of stuff."

That's because he doesn't, normally. A picture is starting to form, and I'm not sure I like what I'm seeing.

"Anyway," Penny says. "I just wanted to talk to you, because I had a great time last week, but the thing is, now that I'm in an executive position...well, it's not technically against the rules for us to see each other, since you don't report to me, but I just want don't want to give anyone reason to talk, you know?"

Right. She's a director now, and I'm still a lowly assistant. Wouldn't want there to any impropriety. I have to bite back a smile at the irony, even though I don't feel particularly amused. Penny is watching me anxiously, obviously worried I'm going to be a dick about it. With some effort, I shove my feelings down. I decided last night that I couldn't see her again, but actually facing it is a different matter altogether. As long as Penny was a possibility, I could pretend that this thing with Derek--whatever the fuck it was--wasn't going to ruin my life. I liked pretending that after it was over, I could have a normal life with a nice girl.

But of course Derek had to take that from me, along with everything else.

"I totally get it," I say to Penny. I force myself to sound as gracious as possible, because none of this is her fault, and I don't want things to be awkward between us. "I had fun too, but we should just stay friends."

"Yes," she says, radiating relief. "Friends, for sure."

"Congratulations again. You deserve it."

"Thanks, Jack. You know, I heard a position for client services associate just opened up. You'd be perfect for it. I'm sure Derek would give you an amazing reference if you wanted to apply."

I have to gulp down some coffee to keep from laughing.

"Okay," I manage. "Thanks, I'll think about it."

I don't really know what else I can say. I don't want Penny to judge me for a complete lack of ambition, but there's also no way to explain to her why putting in an application for a different position right now would be suicide. I don't have a perverted enough imagination to even guess what Derek would do to me.

I guess Penny senses the new awkwardness, because she starts inching backwards.

"I'll let you get back to work." She gives a little wave and heads off, probably to move into a fancy new office with her name on the door. Just the next step in what will undoubtedly be a stellar professional trajectory. I try my best not to be jealous as I watch her go.

A throat clear catches my attention, and I turn to find Derek leaning against the wall, arms crossed. His expression is one of smug amusement. Motherfucker.

I look around to make sure there's no one within earshot.

"So, if I flirt with the janitor, is he going to suddenly get promoted to sales manager?" I demand in a low voice.

"I don't know what you're talking about," he replies, the smirk never leaving his face. "Are you thinking about leaving me, Jack?"

"What?"

"Client services associate? You want to spend your days getting bitched at by our clients?"

"Why not?" I snap. "I've got plenty of experience in bending over and taking it."

His smile turns razor sharp. He straightens and moves closer, resting his arms on the top edge of my cubicle.

"You're just racking up the smartass remarks today, aren't you," he says in a low voice that sends shivers down my back. "Anything else you'd like to add while you're at it?"

I don't want to be cowed, but I remember what he said about punishment earlier, and I absolutely am. I drop my gaze and shift in my chair. The rings on my dick are beyond uncomfortable. I don't want to think about how much worse he can make it for me, with very little effort on his part.

"Sorry, sir," I mutter, even though I know there's no hope that my punishment will be averted or even reduced.

"Grant will be here soon," Derek says. "Hold my calls and make sure we're not disturbed."

He walks away before I can reply, but for once I'm not annoyed by his rudeness. I'm actually slightly cheered. At least one good thing will come out of today.

With Derek back in his office, I'm finally able to log into my computer and start sorting through emails. About ten minutes later, Kevin Grant strolls up, his hands in his pockets and a shit-eating grin on his face. He clearly has no idea what's about to happen, which helps me to return the smile.

"Good morning," he says. "It was nice to see you last night. I trust you enjoyed yourself?"

My smile stiffens as I remember the humiliating state in which he saw me last. Leash, leather thong, and nipple clamps aren't exactly business casual attire. Of course he had to bring up the night before, instead of allowing me to retain the tiniest smidge of dignity, like any decent person would do.

"I found it a little dull, to be honest," I say with a careless flick of my pen. I am determined not to let my embarrassment show. "Derek is expecting you. You don't want to keep him waiting."

It's his turn to grimace through his smile. I know he must hate the insinuation that he's at Derek's beck and call. At least that's something he won't have to worry about after today.