Upward Ambition Ch. 07

(Author's note: this chapter kind of got away from me, but I figured after all this time, you deserve an extra-long installment. I don't know when the next one will be done, but hopefully quicker than this one. All characters in this story are eighteen or older. All of this is strictly fantasy. In real life, enthusiastic consent and safe sex are non-negotiable.)

Derek lets me finish licking my spunk from his shoe and trousers as he idly strokes my hair. I still have my hands clasped behind my back, and I imagine I can feel the heat of his stare on my skin. The burning of my ass is something I've gotten used to, but my scrotum--sore from his punishment and overstimulated from my massive orgasm--throbs in a distracting rhythm.

Despite the pain and humiliation--oh god, or maybe because of it--I'm glad I didn't kick him out when he gave me the chance. The strange frustration that was pent up inside me since yesterday morning when I left his house has dissipated. He said I was desperate for his attention, which seemed ridiculous on its face, but hadn't that been the exact reason I flirted with Penny in front of him? He'd been ignoring me, and I couldn't stand it. There is something heady and empowering about the weight of his full attention, regardless of how helpless it renders me or how painful it is.

This kind of self-reflection is something I'd rather avoid, but it's not like there's much else to think about when I'm busy sucking my own cum off his shoe.

When I've finished, I sit up, only to find that Derek is scrolling through his phone, as if having me naked at his feet is as boring as a shoeshine for him.

"Go clean yourself up," he says, without looking at me. "And get dressed. We have somewhere to be."

I hesitate too long for his liking, and he kicks my thigh, still engrossed in his phone. I struggle to my feet, resisting the urge to cradle my sore balls. I catch a whiff of the pizza that still sits on the coffee table, rapidly cooling.

"My pizza--" I start.

"What about it?" he asks, finally granting me a glance. From his expression, I glean all I need to know about how the rest of this night is going to go.

"Can I at least put it in the fridge?" I ask, defeated. "Sir."

He gives a careless wave and returns to his phone screen. I'm tempted to try to steal a few bites as I take the box to the refrigerator, but I chicken out at the last second. There might be food where we're going, but I don't have high hopes.

"Oh, I almost forgot," Derek says casually. I shove the fridge door shut and turn around, barely biting back a groan that I'm sure would've earned me a slap. Derek leans down to pick up a paper bag that he must have brought with him, though I hadn't noticed it before. He tosses it, and I fumble a little to catch it.

I peek inside, my heart clenching with terror at what I might find, but instead of some new instrument of torture or humiliation, I find a pack of razors and a bottle of shaving gel.

I look up at him questioningly, even though I already know what he's going to say.

"Shave," he says, and then adds, with a meaningful quirk of his brows, "everywhere below the ears."

I clamp my jaw down on my objection, because it's not like it will make any difference. I head into my bathroom and take a quick shower, treating my tender privates with care but scrubbing the rest of my body pink. I don't have a douche (and wouldn't use one on myself if I did), but I at least make a cursory attempt at cleaning my hole. Despite how often Derek has violated me there, or made me violate myself, it's still an odd, alien feeling. I wonder if I'll ever get used to it.

Then I rip open the pack of razors and start the tedious task of shaving. My face is easy of course, as is my chest, stomach, and underarms. I don't have much hair on my arms, but I shave them anyway, because I'm sure Derek would love to punish me for not being thorough enough--which is also my reasoning as I take the razor to the tops of my feet and my toes. Thankfully I don't have any hair on my back, because there's no way I'd be able to reach.

My legs take longer, and I nick myself a couple times around the bony parts of my ankles and knees, which doesn't bode well for the rest of my task.

It takes some creative yoga posing, but I manage to shave my ass, even between the cheeks. Although there's no one to see me, I'm still red-hot with embarrassment. That just leaves my crotch. I use a new razor and a shit-ton of gel, and I grit my teeth as I work slowly around the curves of my pelvis, all along the root of my cock, and then--most painstakingly of all--my ball sac.

By the time I'm finished, my jaw hurts from how tightly my teeth were clenched, but my private parts are completely hairless--and thankfully intact.

I dry myself off and rub my hair vigorously with the towel. I dig around under the sink and find a dusty old bottle of baby oil, which I apply liberally all over, in hopes of avoiding razor burn. And I'd be lying if I said I'm not also thinking about Derek's hands on me, fingers gliding sensually across all that newly smooth skin. The thought brings a shiver with it that has nothing to do with my damp hair.

As a last thought before I leave the safety of the bathroom, I brush my teeth, even though I'm sure Derek will be filling my mouth with something before the night's through.

I have no idea where we could be going on a Monday night, and I don't bother asking, because if Derek wanted me to know, he would have told me. In my bedroom, I vacillate between clothing choices for a few minutes before deciding on the khakis and pale green collared shirt I was going to wear to work tomorrow, though I leave off the tie. No need to make myself more uncomfortable than necessary.

Back in the living room, Derek barely glances at me before pocketing his phone and heading out the door. I guess my shaving job doesn't warrant inspection. I grab my wallet and keys from the coffee table and follow him. His shiny black sedan and driver are waiting for us across the street from my apartment building, looking utterly out of place in the somewhat seedy neighborhood. Derek doesn't seem to notice or care about the stares we garner from passersby and through cracked blinds as the driver rushes to open the rear passenger door for us. I slide in quickly behind Derek, keeping my head down and hoping no one recognizes me. The last thing I need is to be mugged on the way home some night because one of my less-savory neighbors thinks I'm secretly rich.

By the time the car lurches into motion, Derek is already back on his phone. I would pull out mine to pretend to be busy as well, but I realize I left it at home on the kitchen counter. Great.

"Hasn't anyone ever told you that's rude?" I ask, after a few minutes of silence.

"Still haven't gotten enough attention tonight?" he asks with a smirk. "Needy little thing, aren't you."

My cheeks flush, but before I can come up with a response, he leans down and grabs a leather briefcase from beneath the driver seat. He withdraws a small parcel wrapped with red tissue paper and tosses it into my lap. I blink down at it in surprise.

"For me?"

Derek nods, his slow-spreading smile sending a familiar chill down my spine. I unwrap the paper and lift the item inside. I feel my cheeks flush from pink to scarlet. It's a black leather thong.

"You shouldn't have," I say dryly.

"Put it on."

"What? Now?" I look around nervously. The windows are heavily tinted, and there's a privacy screen separating us from the driver, which is a relief, though I don't know how much of our conversation he can hear.

"Do you want me to lower the screen so he can watch?" Derek asked, his finger hovering over a button on the door.

"No!"

"Then do as you're told."

I bite my lip in consternation, but my fingers are already moving to undo my khakis. Derek slings his arm over the seat back and props his right ankle on his left knee, perfectly at his leisure. He looks to be enjoying himself.

"Might as well take off the rest of your clothes while you're at it," he says, still wearing his wolfish grin. "You won't be needing them where we're going."

Well, fuck. I haven't been paying attention to our route, but I know we're headed in the opposite direction of his house.

"Where is that?" I ask, on the off chance he might take pity on me. He only shakes his head, his dark, hungry gaze trailing along my body as I toe off my shoes and socks and wriggle out of my pants and underwear. Stubbornly, I leave my shirt on until after I've pulled on the thong, granting my dick the maximum amount of privacy. Newly hairless, I feel unbearably exposed.

I'm more than a little awkward and undignified as I adjust my junk in the tight leather pouch. I can feel the string in the back riding into my ass crack. I've never worn a thong before, and it's probably obvious, considering my entire body is currently flushed with hot embarrassment.

I cross my arms protectively over my chest as Derek reaches over and fondles my package gently. I try not to squirm as my cock--which had been half-hard since the moment he told me to strip--immediately responds to his touch, straining against the leather. With gritted effort, I manage to keep myself from thrusting into his hand, so at least I maintain that tiny bit of dignity.

But Derek is quick to strip me of that too as he reaches again into the briefcase and pulls out my old nemesis, the black leather collar. I expect him to make me put it on as well, but he curls his fingers over my inner thigh and forces me to slide closer to him. I swallow hard as he buckles it around my throat, his fingers raising goosebumps on my skin everywhere they touch.

"Almost perfect," he murmurs, brushing his thumb along my jawline.

He retrieves one more item from the briefcase. A small velvet box. I'm wondering if he actually bought me a real present--like a watch--when he pops it open. On a little bed of satin rests two silver clamps. He lifts one, and I see that it has a small leather bauble dangling from it.

"Play with your nipples," he says, his voice low and tinged with arousal. He grips the back of my neck below the collar, not painfully, but tight enough to remind me who's in charge. "Get them nice and hard."

I don't want to play with my nipples. And I definitely don't want to wear those clamps. But Derek has already dragged me so far down the path of things I don't want to do that I'm sure I can ever find my way back to "no."

I begin to rub both nipples between thumbs and forefingers. Despite myself, sparks of stimulation race straight down to my cock and balls. My breathing quickens as Derek leans in close. His lips work up the side of my neck with slow, deliberate care. I squeeze my nipples harder on instinct. My breath hitches as his tongue slides along the shell of my ear. He bites down on my earlobe, and I let out a helpless moan.

I'm so caught up in the sensation that I barely notice when Derek brushes my left hand away. I definitely notice when he snaps the clamp onto my nipple. I jerk and yelp, reaching automatically for the offending clamp, but Derek's hand closes over my wrist in an iron grip. He tsks me softly and lowers my hand down to my lap. I dig my fingernails into my thigh to stop myself from trying to yank off the clamp again.

Instead of attaching the second clamp, Derek presses it into my other hand. I whimper even as I wrap my fingers around it obediently. I take a deep breath to steel myself. My hand is trembling so much it takes me several seconds to position the little rubber lips around my nipple. The fact that Derek is still flicking his tongue against my ear makes it even more difficult to concentrate.

I release a hiss of pain when I finally manage to attach it. My other nipple is already starting to go numb, which is a relief, even though I know the real pain comes whenever Derek decides to yank it off. To make things worse, the leather baubles are weighted like fishing sinkers, creating a constant tugging sensation.

"You didn't thank me for your gifts, Jack," Derek whispers into my ear. "Hasn't anyone ever told you that's rude?"

I close my eyes, resisting the sudden, overwhelming urge to tell him to fuck off.

"Thank you, sir," I manage.

"Mmm, almost convincing." He hooks his finger in the back of my collar and drags me over his lap.

"Wait," I sputter, flailing a little over his thighs. "What did I do?"

"Nothing." He strokes my back in a gentling motion, and I settle reluctantly. He runs his hand over the curve of my butt, thumb hooked beneath the string before he lets it snap back into my crack. "But it seems like a waste to have this ass on display without a bit of color, and you've already lost the lovely shade from earlier."

I groan into the seat as his hand smacks down. In fairness, the spanking is less severe than my punishment from earlier, and he leaves my balls alone in their leather pouch. Somehow, that's almost worse, because the moderate sting, coupled with the awareness of his erection against my side, makes me so hard that my squirming has nothing to do with trying to escape the spanking. God, I really am a pain whore.

I'm saved from my humiliation--or at least this particular one--when the car rolls to a stop. Derek lets me kneel up, and I see that we are in some kind of parking structure, next to shiny elevator doors.

"Are you going to be a good boy tonight?" he asks, flicking one of the baubles hanging from my nipples and making me wince.

"Do I have a choice?"

He smiles, not quite kindly, as the chauffeur opens the door. I'm careful not to make eye contact with the driver as I climb out behind Derek, but a quick glance at the man's face confirms that his expression is as stoic and uncaring as the butler's was. I wonder how much money these men make just to keep their mouths shut and their eyes averted, and I wish I'd managed to land in one of their positions instead of my current one. The pay is undoubtedly better.

Once the elevator doors close on us, Derek pulls the leash from inside his jacket and clips it onto my collar.

"Hands and knees," he says. "You'll be crawling for the rest of the night."

"Are you serious?" I ask, even though I'm already sinking to my knees on the cold floor of the elevator. The floor numbers are rising steadily. Tenth floor. Eleventh floor. Twelfth floor.

"Don't worry. You won't be alone." I can hear his smirk rather than see it. It doesn't make me feel better.

"Can I at least know where we're going?" I mumble.

"Charity fundraiser."

I assume he's being facetious, but before I can reply, the elevator dings to a stop at the penthouse. The doors open, revealing--to my shock--what indeed appears to be a fundraiser. There are men in expensive suits and women in glittering cocktail dresses. Waiters hover around with trays of champagne flutes and hors d'oeuvres. The only difference between the scene before me and any other one-percenter party from the society pages is the number of half-naked (and in some cases, completely naked) people on their hands and knees.

What the fuck?

I'm so entranced by the sight that I don't notice Derek has moved until the tug of the leash gags me. I scurry after him, the nipple clamps swaying uncomfortably with my movements. My kneecaps bang painfully on the polished hardwood floor, and I breathe a sigh of relief when we make it onto a plush maroon rug.

Derek accepts a glass of champagne from a passing waiter. I dart a furtive glance around the room. We're in a large open foyer, with crystal chandeliers and several pieces of understated but clearly designer furniture. My eyes snag on a woman stretched out on a chaise lounge, her pale green silk dress pushed up around her hips. A muscular man, nude except for a pair of lacy panties, is hunched between her legs, eating her out with the vigor of a starving person at a buffet. The woman's head is thrown back in wild abandon, one arm flung over her eyes, her glossy curls half-fallen out of her fancy updo. A couple of people nearby are enjoying the scene as they sip their drinks, but with the air of connoisseurs partaking of fine art, not voyeurs at a peep show.

Elsewhere, I see a blonde woman in a leather bondage harness on her hands and knees. She presses her face down to the floor and sticks her round ass up in the air as a woman in black leather lingerie and a huge strap-on dildo mounts her. Two men in suits look on appreciatively. One of them is gripping a leather flogger that swings idly at his side, though he looks poised to use it at any moment. The blonde moans as loudly as a porn star as she's pounded from behind, but the sound is only one of dozens in the room's cacophony of sex acts.

To my left, startlingly near, a twink in nothing but a pink collar and matching fuzzy cat ears is sucking sloppily on his master's dick while the man chats with a woman in a red cocktail dress. I hear a couple snatches of the conversation; it seems they are discussing "quarterly revenues" and "outstanding profit margins." Other than his gentle, proprietary stroking of the twink's hair, the man pays him absolutely no attention.

"Who are these people?" I mutter. I didn't really intend to say it aloud, but too late now.

"They are your betters," Derek said. "And to make sure you don't forget it, you're going to kiss the feet of every person I speak to."

Fuck. I swallow down a protest. Derek's not exactly a social butterfly. Maybe it won't even come up.

Of course, no sooner do I think that, than a woman walks over, teetering on ridiculously high stilettos.

"Derek, darling," she says, leaning in to kiss both his cheeks in the European fashion. "I hoped you would stop by."

"Nice to see you, Gina. It's been a while."

"It really has." She has a posh British accent and is wearing a shimmery, body-hugging dress that shows off her impressive curves. In my previous life, I would have definitely embarrassed myself by staring. Now, I get to embarrass myself by shuffling forward and pressing a kiss to each of her shiny, pointy toes.

She catches me under the chin with one foot and tilts it up, forcing me to turn my face upward. I manage to meet her eyes for half a second before dropping my gaze.

"This one's new," she says conversationally.

"Yes." Derek gives my leash a tug, forcing me to sit back on my heels.

"Cute." She twirls one perfectly manicured finger. "Let me see that ass."

I gape up at her for just a moment too long, and Derek gives the leash a brutal yank that makes me gag and cough. Helpless, I turn around and bend over, arching my back to give her a good view of my reddened cheeks. I wince as she prods the tender skin with one of her toes.

"Beautiful color," she remarks.

"He gives me enough occasion for it," Derek replies, letting me sit back up.

"Oh does he?" she asks with a dainty little laugh. "My boy Sammy is much the same. He was an absolute little shit today, so he won't be joining the party. I've had him strapped into the paddling machine for the past three hours, and that's where he's going to stay."

"Paddling machine?" Derek echoes, with a piqued curiosity that didn't bode well at all.

"It's positively a lifesaver," she says, bobbing her head enthusiastically. "Between the foundation and my other obligations, I don't always have the time or energy to devote to punishments that I'd like. You can change out the types of paddles and adjust the speed and rhythm." She gives my butt another solid poke with her shoe. "You're welcome to bring this one by anytime he needs a good session."

I gulp in the silence that follows, as Derek clearly considers the offer. My ass is already burning at the thought.

"Jack would enjoy himself too much," he says, with a touch of dark humor. "He's an incorrigible little pain whore."