Upward Ambition Ch. 08

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Jack endures a new punishment.
9k words
4.81
16.8k
13

Part 8 of the 10 part series

Updated 09/14/2023
Created 06/19/2020
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wirtydord
wirtydord
132 Followers

(Author's note: Sorry about the long wait! I'm still here and still want to finish this story. I've just got life stuff to deal with in the meantime. Thanks for reading and for your encouraging comments! As always, what follows is purely for the purpose of fantasy. Seriously, don't model any real relationships on these two. In real life, enthusiastic, uncoerced consent is absolutely vital.)

#

I wake up in the backseat of Derek's car, curled up with my head in his lap. I shiver at the sensation of his fingers in my hair, stroking softly. For a long while, I'm scared to move and disrupt the rare moment of peace. I'm not sure what time it is, but considering the drive to the party was only about half an hour from my apartment, I'm guessing he's not just going to drop me off at home for a good night's sleep. Fuck, how is it only Monday night? (Who the hell does a charity fundraiser on a Monday? I guess people rich enough that it doesn't matter if they sleep in.)

Slowly, I roll onto my back, blinking blearily up at him. He's resting with his hand on his neck, his elbow propped against the window. He stares out pensively, the flash of moonlight through trees illuminating his features in streaks of silver. I think about his indecipherable expression during Danny's caning. I wish I could know what was going on in his head, but I'm as in the dark now as I've ever been.

The car turns, and the wheels rumble from one surface to another. I'm already pretty sure I know where we're going, so I'm not surprised when the car rolls to a stop a few minutes later and I sit up to find the stately façade of the Harrow mansion, artfully lit with exterior lights like a movie set. My heart begins to beat a little faster--from anxiety or anticipation, I'm not sure.

The driver opens the door, and Derek slides out wordlessly. He's still got my leash in hand, so I'm forced to scramble out behind him before I get dragged out by my neck. The smooth grey flagstones of the circular driveway are swept clean, but it doesn't make me feel any better as I drop to my hands and knees for the journey up the broad front steps into the main foyer. One of the grand double doors creaks open at our approach, and the butler steps out with a nasally greeting--for Derek, at least. I am pointedly ignored.

"Groves," Derek says, by way of greeting. He hands off my leash to the butler like I'm the fucking family dog and says something to him in low tones that I can't make out. Then he disappears into the dim interior of the house.

Still without addressing me, Groves leads the way inside, taking the time to shut and lock the door behind us, then tap something into the security system screen on the wall. For the first time, I'm struck by how helpless I truly am out here. No car, no cell phone, no clothes. No way to even leave the house without alerting everyone.

I don't get time to think on it further as Groves heads, stiff-backed, to the front stairway. I climb up after him, hating how natural it feels on my hands and knees. How long until I'm brainwashed into crawling into work one morning?

After the stone driveway and hardwood floors, I'm grateful for the thick shag rug running the length of the corridor. The house is so stupidly oversized--and I'm so tired--it feels like we walk/crawl for a mile before Groves finally stops to push open a pair of mahogany double doors. This isn't the same guestroom I was in over the weekend, and the butterflies in my chest turn to wasps as the butler flips on a couple light switches. Illuminated is a bedroom that is easily twice the size of my entire apartment, tastefully decorated in shades of gray and midnight blue. There is a California-king-sized four-poster bed, along with several tall bookshelves and a seating area with leather armchairs and ottomans around a slate-stone fireplace.

I don't have much time to gawk while Groves crosses the room to another door and pushes it open, revealing a bathroom of a size that is proportionate to the room, but still entirely too large for any normal human.

"Mr. Harrow has given you leave to use the facilities," Groves says in a pinched, disapproving tone, as if his master had suggested they let a random hobo move into the powder room and stay a while. He leans down to unclip the leash.

"How generous of him," I say dryly.

Groves titters and refuses to meet my eye as I stand up and shut myself inside the palatial bathroom. There's a glass walk-in shower, with a stone bench and rainfall showerhead like in a spa. In the other corner is a jacuzzi tub big enough to fit three people at least. I'm surprised the toilet doesn't talk to me as I open the lid and relieve myself. I flush and pause to examine myself in the mirror. I look about as terrible as I expected. My hair's a mess, and my eyes are puffy and tinged underneath with dark circles. There are two sinks, but only one has a toothbrush in a holder, along with a comb, an electric razor, an open bottle of shaving cream, and a hand towel that looked like it had been tossed there in the moment, not neatly folded for the use of a guest.

I stare for a long moment before it finally hits me. I'm in the master suite. Derek's suite. This is his bathroom, not some empty, unused guest space in a house full of them.

I wash my hands, unable to stop myself from studying every detail from the brand of soap to the softness of the towel, as if it somehow matters. More than anything, I want to start opening drawers and cabinets, to uncover any secrets that might be hidden in this inner sanctum, but Groves is waiting, no doubt with a sharp ear at the door. And I wouldn't put it past Derek to have security cameras in here too, for the express purpose of spying on his overnight guests.

Does he have overnight guests though? I've booked hotel rooms before for his dates, always a luxury suite in a five-star establishment. It never really seemed like he had interest in bringing them home for a quiet night in. And besides, I'd never known him to go out with the same woman more than a couple times.

I shake the idiotic thought from my head. There's nothing special about me. Him allowing me into his bedroom isn't some special show of trust or affection. I'm still in a leather thong and dog collar for fuck's sake.

You're my fucktoy, to do with as I please, he told me, only two nights ago. I can't let myself forget that.

I open the bathroom door and nearly jump out of my skin to find myself face-to-face with Groves. He is holding up the clip of the leash expectantly. Right. Silly me to think we were done with that for the night.

He fastens it to the collar, and with a sigh, I drop back to my knees. It seems an entirely futile exercise, considering we only go so far as the bed. He has me kneel at the bottom left corner, where he very theatrically ties the leash around the wooden post, as if I really were an untrained dog. I stare with some incredulity as he leaves the room, the door closing with a click behind him.

It's a whole new brand of humiliation, to be kneeling here as if I lack the ability to simply stand up and untie myself--or remove the collar altogether.

And yet...I don't.

I kneel obediently and wait, even as fury--at myself, at Derek, at fucking Groves--simmers caustically in my chest.

To distract myself, I scan the contents of the room, hoping to at least glean some insight into my boss's private life. To my dismay, Derek's bedroom is as impersonal as he is. The books are all stuffy-sounding business titles, probably leftover from his college days or inherited from his father, and a few language books. I already know he is fluent in Mandarin, Japanese, and French, and he knows enough Spanish, Italian, and German to get through a business luncheon. I took some Spanish in college to satisfy a language requirement, but I didn't remember more than Me llamo Jack and Donde esta la biblioteca?

I don't need to see his bookshelf to be reminded how accomplished he is. Feeling vastly inferior to Derek Harrow in every possible way is one of the few things that comes naturally to me.

One other object in the room catches my eye--a picture frame on the nightstand. I squint for a better look, not daring to move from my spot. It's a woman. At first, I think it might be the ex-fiancée he told me about--maybe he's still hung up on her? But no, the more I look, the more I can see in the cut of her hair and the fashion of her clothes that this is a photo from a couple decades past at least. The photo was snapped mid-laugh, and her bright eyes are angled down and away from the camera. I follow the line of her gaze and realize that the shape at the bottom corner of the photo is a little boy. She's holding his hand between them, but the rest of him is blurred slightly, like he was in motion when the shot was taken. The soft features are hazy, but from the shock of dark hair and the light eyes, I have no doubt it's Derek.

I know Mike Harrow's wife died almost thirty years ago in a car accident, but this is the first time I'm able to wrap my mind around the fact that she was also Derek's mother. That he was a little boy once, gripping his mother's hand and unable to stand still for a snapshot. He would have still been a little boy when she died--maybe not much older than that picture.

Despite myself, the fury in my chest has begun to give way to an aching sympathy that I know Derek would utterly despise. He isn't the type to appreciate pity in any form, however justified.

The door opens, and I jerk my gaze away from the photo, trying my best to regain a neutral expression. Derek enters without any acknowledgement of my presence. He's carrying a glass tumbler with a couple fingers of amber liquid, probably another whiskey. He sets it on the bedside table--I can't help but notice that he smoothly turns the picture frame facedown at the same time--and then disappears into a door next to the bathroom. When the light flickers on, I see that it is a closet, just as oversized as every other room in this place.

It is odd, watching him move automatically through his routines, shrugging off his suit jacket and placing it on a hanger, removing his tie and his belt, toeing off his shoes and socks and tossing his cufflinks into a little glass bowl on the chest of drawers. Coming so soon on the heels of the bizarre charity fundraiser, the mundane domesticity of it is whiplash. I'm not sure if I want to laugh or cry.

"I don't think Groves likes me very much," I say. My voice sounds too loud in the silence.

He shoots me a sidelong glance, and for a moment I wonder if I'm about to be punished, even though he never told me not to speak. Then he smirks and goes back to unbuttoning his shirt.

"Groves doesn't care about anything but the estate and the family name. If my father had disinherited me, Groves wouldn't like me either, but since the old man never got around to it, he stays on to vouchsafe the Harrow legacy."

I'm not sure I'll ever understand the peculiarities of old money--who cares about things like "legacy" in this day and age? And I definitely don't get why a man who isn't even part of that money feels the need to dedicate his life to preserving the family's status and reputation. But the snooty butler's motivations are hardly my concern.

Derek emerges bare-chested from the closet, his trousers riding low on his hipbones, underlining the perfection of his swimmer's physique. I tell myself to stop staring, but it seems idiotic at this point to pretend that I have zero attraction to him, when a couple hours ago I eagerly swallowed down his cock of my own volition.

He doesn't notice my rudeness, or maybe he's just used to people staring. A devilishly handsome, spectacularly arrogant multi-millionaire doesn't exactly move through any circles unobtrusively. He reaches down and unbuckles the collar. Though it wasn't too tight, I can't help but breathe easier.

"Get on the bed," he says, and the low timbre of his voice sends a surge of need straight to my groin.

I climb onto the bed, trying not to look too excited about it. It's not like private sessions with Derek are ever fun, but thinking back on the mind-blowing orgasms I've experienced at his hands, I can't pretend like I don't get anything out of it.

I lay down on my back, not sure how he wants me. My chest is rising and falling rapidly, and my pulse rings in my ears. I try in vain to calm my breathing. Derek walks to the bedside table and takes a sip from his whiskey, the essence of nonchalance, as if he doesn't have a naked subordinate stretched on a bed (his own bed), trembling like a leaf.

Still holding the glass in his left hand, he sits on the edge of the mattress, his keen eyes trailing along my body like red-hot brands. I'm suddenly conscious of how soft and untoned my own body is, how the muscles I built running track in high school and college have shriveled with disuse and too many frozen dinners. I try to push the thought from my mind, along with the urge to curl into a ball. Derek trails a finger up my arm, raising goosebumps in its wake. Judging from the feverish heat of his gaze and the growing hardness in his pants, Derek is not thinking of my body in the same ungenerous terms. Somehow that turns me on even more, and though I'm helpless under his hands, a strange sense of power blooms inside me.

"You've been a good boy tonight, Jack," he purrs. He runs his thumb across my lips, and without thinking I take the tip of it gently into my mouth, flicking at it with my tongue. "Are you going to keep being good?"

I nod fervently. He gives me a razor-sharp smile and replaces his thumb with his first two fingers, pushing them in deep enough that I nearly gag. I overcome the reflex and start to suck. My slavish humility barely registers with me anymore. Submitting to him has become second nature.

He withdraws his fingers, and I'm afraid he's going to torment my chafed and aching hole some more, but he only smears my own spit across my cheek. He grabs my left wrist and pulls it up to rest it on the pillow above my head, and then he takes my right wrist and crosses it over my left.

"Keep them there," he says. He doesn't add a threat. He doesn't have to.

Still moving with infuriating insouciance, he reaches down, hooks a finger into my thong, and tugs it down. I bite my lip as my half-erect cock pops free. I blush at the smirk he gives me. He yanks the thong the rest of the way down, pulls it off my ankles, and tosses it next to me on the bed. Even though I'm expecting it, I can't suppress a gasp when he encircles his fingers around the head of my cock and gives it an experimental little squeeze.

"Do you like that, slut?" he asks, as his hand moves up and down with just enough pressure to be tantalizing, but not enough to bring me anywhere close to the edge.

I manage a nod.

"Answer me." He gives the tip a vicious pinch, and I squeak.

"Yes, sir!"

"How about this?" He drops his hand lower and fondles my balls, just a little roughly.

"Yes, sir," I whisper, my toes curling.

"And this?" He releases my balls and takes my left nipples between his thumb and forefinger. Before I can brace myself, he twists ruthlessly.

My hand flies down, and though I stop myself before I grab his wrist and slam my hand back into place above my head, I know it's too late. I also know, from his wicked grin, that he was expecting that. But to my shock, there is no swift punishment.

"That's the only freebie you get," he says. He pinches my nipple again, and this time I hold my position. "That's better."

"Thank you, Mr. Harrow," I manage.

"Don't thank me yet. The night is far from over for you." He sets his glass tumbler down on the center of my chest, not bothering to warn me what will happen if I let it spill. I redouble my efforts to calm my erratic breaths.

He swings his leg over my waist to straddle me, though he's careful not to give me the satisfaction of even brushing against my shaft. His face is a shadowy silhouette above me, haloed by the bedroom light, but I can still make out the mischievous twist of his mouth and the dark gems of his pupils, dilated with arousal. He plants his hands on either side of my head and leans down. He traces his tongue along the bite mark he left on the curve where my neck meets my shoulder, and I wince at the twinge of pain, though it does nothing to kill my erection. You're nothing but a little pain whore, aren't you?

His lips hover near my ear, breath warm.

"I can do anything I want to you, can't I?" he whispers, so close that I can feel the tickle of his lips against the shell of my ear. "Anything at all, and you'll just lie there and take it."

I'm not sure if it's a question or not, but I nod, just in case. I can't quite summon my voice.

I'm expecting pain, but instead he brings his lips to mine, joining them in a kiss that is both passionate and hungry. His tongue slides into my mouth, coating every inch of it, like he's trying to make sure I can taste nothing but him. A tenuous moan rises in my throat. I feel like he's devouring my voice, my breath, my very essence.

Just as I'm thinking I could happily stay here forever, he pulls away. I swallow down a disappointed sigh. His eyes gleam as he takes a sip of his whiskey, then returns the glass to my chest. He runs his thumbs over my nipples, and I brace myself for pain, but again, he surprises me. He softly tweaks my sensitive nubs, first rolling them gently beneath the pads of his fingers, then licking them each in turn as if they were sweet little hard candies.

My back tries to arch with the delicious sensation, very nearly tipping over the whiskey glass before I manage to flatten myself.

He smiles like the cat that got the cream. I bite back the urge to tell him to fuck off.

He trails both hands down my chest, fingers playing along my ribs. I'm not overly ticklish, but I still have to fight to keep from squirming. My breaths come in shaky gasps. He lowers his mouth once more, and I ready myself for teeth, but it's his tongue again, slow and exploratory. It's like he's mapping my body through touch and tongue alone. It is possessive. Proprietary. And unbelievably erotic.

He dips his tongue into my navel, and I feel it in the core of me. I want to touch him back, run my fingers through his hair, taste the salt of his sweat and masculine musk on my own tongue. I squeeze my hands into fists, struggling against the invisible bonds he created with only the power of his command.

He takes up his glass again, and I gasp at the sudden flood of cold on my genitals as he dumps the last of the contents over my crotch. Before I can even wrap my head around that, he's already dropped his mouth to the hollows of my pelvic bones where a tiny bit of amber liquid has pooled. He kisses away the moisture then licks his lips. My cock jumps at the mere image.

I'm groaning before his tongue has even touched my shaft. It strains upward like a begging dog as he laves away the alcohol. He dips down to my scrotum next. The whimper that escapes me sounds almost pained. He takes his time replacing every drop of whiskey with his own saliva, until my balls are practically throbbing, ready to explode.

"Please." It comes out as a bare whisper. When he ignores me and starts to mouth my sac, swirling his tongue against each ball in turn, I groan and try again, louder this time: "Please."

He raises his head, just enough to meet my eyes. His breath is a warm susurration across my glistening cock.

"Please, what, Jack?"

"Please, Mr. Harrow, may I come?"

He only smiles, as if to say what do you think, and returns to the task of torturing me with ecstasy. When he wraps his lips around the head of my penis, the rapture of it is excruciating as I strain for self-control. Every particle of my being wants to give into the orgasm that threatens to roll over me. My hands twitch with the desire to grab his head--whether to push him off or further onto my shaft, I'm not sure.

wirtydord
wirtydord
132 Followers