Upward Ambition Ch. 07

There's a rumble of excitement through the crowd, and I look to the stage. A young man, naked and blindfolded, is being led onto the stage by a huge man wearing black leather pants and jacket, unzipped to show off his tanned, muscular chest. The top half of his head and face is covered with a hood like an executioner. The naked slave stumbles a bit at the stage, and the dominant, who must be twice his size, simply heaves the slave over his shoulder like a sack of potatoes and climbs the steps. He puts the boy on his feet in the center of the wooden frame and starts to fasten the restraints on his wrists and ankles.

There's no mistaking the buzz of anticipation in the air. It reaches a crescendo as the dom steps away, giving the room a clear view of the naked boy--Danny, wasn't it?--chained spreadeagle in the frame, still blindfolded and completely helpless. His milky pale skin and his small pink cock and his tender little balls are all utterly vulnerable to the ravenous eyes and lustful appetites of the assembled guests, assuming they are willing to pay. Thanks to the artfully angled mirrors, even his buttocks, round and pert and practically begging to be assaulted, are on full display.

Gina takes the dom's extended hand and climbs onto the stage to face her patrons. She smiles broadly and starts into a spiel thanking everyone for coming. I don't have a chance to listen because at that moment my new enemy returns, bearing a silver tray with a bottle of lube and a monstrous purple dildo, covered in hideous bumps and ridges. I shudder and completely forget my resolve to remain stoic. Fuck, fuck, fuck.

My gaze darts to Derek. Surely he'll take one look at it and realize it's too big, too barbaric, too much.

He considers the proffered tray for a moment, and for a millisecond, I have hope. Then he smiles serenely up at the waiter.

"Perfect."

A sound escapes me. Somewhere between a gasp and a sob. For the first time in a while, I truly begin to count the cost of just getting up and fleeing this twisted fetish playground. It's not like Derek would chase me down and drag me back. I could leave the state, change my name, and start over somewhere new. Would Derek go through the trouble of tracking me down just to sue me?

Even as I tell myself that I can pull it off, that I can make my great escape and never look back, my legs refuse to move. My body refuses to save me.

"Would you care to do the honors?" Derek asks the waiter, who is radiating gleeful malice as he nods.

I remain frozen to the spot, hot tears building up behind my eyeballs, threatening to spill.

"Please," I whisper. I'm not sure if I'm talking to Derek, the waiter, or just the universe in general.

Derek, at any rate, is unmoved by my plea. He yanks on the leash.

"Get up here before I tell Gina to put you in Danny's place."

Honestly, in this moment, that sounds almost preferable. But seeing as my body is too weak with terror to offer much resistance--not to mention the fact that I need to breathe--I'm pulled easily to my feet and made to bend over the arm of the chair, my hands clasping the other arm, my face hovering above Derek's lap.

Gina is still going on about the foundation's annual goals and such, but I can sense more than a few guests' attention has been claimed by this new spectacle.

The waiter kicks my legs wide apart without bothering to ask, as if I'm too stupid to comprehend even a simple command. In this state, I probably am.

"Don't tear him," Derek says simply. "He has work tomorrow."

And I realize that's the only ounce of mercy I can expect from him.

The squelch of the lube bottle. I try to steel myself, but I still jump when the waiter's cool, wet fingers press against my pucker. I swear I hear him snicker. I indulge in a fantasy of turning around and punching his smug face, which soothes me just enough to hold steady while he shoves two fat fingers roughly into me. I guess to Derek this doesn't count as "sharing his toys."

I take deep breaths and focus on relaxing my hole. Derek has used me enough at least that even when there are four fingers stretching me out, I'm able to breathe my way through the slowly expanding pain.

When the fingers are finally gone, I release a sigh of relief, before remembering what comes next. Derek knows me too well, because just as I reflexively start to rise in panic, he grips the collar, keeping me in place. With his other hand, he starts to flick at the teardrop weight dangling from my nipple, first one, then the other. My nubs are blessedly numb, but nonetheless the new sensation makes me squirm.

Something wet and cold and definitely not finger-shaped presses against my anus, and I freeze immediately, my lungs shriveling in my chest. Just as the silicone dildo starts to press against my stretched--but not nearly wide enough--hole, Derek yanks off one of the clamps.

Breathless as I am, my howl of pain is nearly soundless, filling up my throat until I'm drowning in it. As pain radiates from my left nipple, a new pain explodes in my asshole as the waiter penetrates it with the first inch of the dildo. I gasp for air, trying to find some semblance of equilibrium as I'm assaulted on two fronts. Tears are falling freely now. The dildo invades another inch, stretching me wider than I ever thought possible. Surely it's too much for me to ever recover. A distant part of my brain thinks, That old pervert will be thrilled. Now I can be the perfect fist puppet.

Something like a laugh bubbles in my throat. I must be nearing full-on hysteria.

Derek wrenches the other clamp free, and whatever barrier my mind erected to protect me from the worst of this torture crumbles. My entire body surges with an agony that is somehow both searing hot and ice-cold. Once again, Derek forestalls my reflexive reaction by wrapping his hand around the back of my neck and pushing my face hard into his lap. A scream rips from my throat, but it's effectively muffled in his expensive trousers.

The waiter has not paused his slow assault on my back channel, and as the pain in my nipples fades, my awareness is overwhelmed by the alien sensation of being stuffed fuller than I've ever been in my life. It feels like my intestines are rearranging around the invader. And worse, I can feel every ridge, every bump of the dildo, scraping along every inch of my chute.

A low moan vibrates in my chest but is again muted by Derek's lap. Along with my excruciating awareness of the monster dildo filling me up, I slowly realize that my face is buried in his crotch, my mouth and nose crushed against the familiar hard shape of his cock. My nostrils are filled with the musky, masculine scent of him, and despite everything, my mouth waters. I move my lips experimentally and am rewarded with a satisfying twitch. His hand squeezes tighter on the back of my neck, but I don't know if it's an admonition or encouragement.

The waiter gives the dildo one final, epic push to the hilt. I jolt and scream until I'm well and truly out of air. Only then does Derek allow me to raise my head the slightest bit, just enough to suck in some short, panicked breaths. I realize I've left his lap damp with my spit and tears. I wonder vaguely if he will punish me for that, but I can't bring myself to care.

My ass is throbbing steadily, and I'm convinced my body will forever be molded to the dildo's gruesome shape. I'm slowly coming back to myself. The waiter is gone, thank god. Derek must have waved him off. Even though my entire universe has narrowed to this singular point of pain, the show has gone on. I hear a slapping sound and look blearily to the stage to find that someone has purchased the barehanded spanking for poor Danny.

His mouth forms an O as the dom's meaty hand, which is almost big enough to cup his entire ass, smacks again and again, changing up the placement and angle of each blow. Danny's cock, which is small but proportionate to his skinny, boyish figure, is at half-mast and flopping forward with the thrust of his hips. He is still blindfolded. I guess keeping him in the dark about what comes next is part of the fun.

Derek's hand on the back of my neck is now massaging my corded muscles, and the unexpected gentleness is a whiplash that brings new tears to my eyes.

"Kneel down," he says softly.

My body obeys without any input from my brain, and I give a low moan as the silicone monster cock inside me shifts and rearranges my innards once more. I have to keep my knees spread wide, which only compounds the feeling of helpless exposure. Derek keeps his hold on the back of my neck, fingers sliding beneath the collar, but his grip is so loose it's more like a reminder that he's there than a restraint.

I'm suddenly impossibly exhausted, and I rest my cheek against the chair's arm, letting myself be lulled by the rhythm of Danny's various punishments. The spanking is done and has been followed up with a brutal flogging on his chest, the fronts of his thighs, and occasionally his crotch. He cries out after each hit as the leather tails raise streaks of red across his pale skin. The crowd is fully entertained now, letting out a chorus of approval whenever the dom lands a particularly powerful swing or the tails catch Danny's defenseless little cock and his cries turn into a squeak.

Most people don't buy more than five or ten swings of their instrument of choice. We cycle through a few different ones, occasionally doubling back to the flogger or a good old-fashioned spanking. When someone finally drops the big bucks on a butt-fuck, the guests go wild. You'd think we were at a back-country cock fight rather than an upper-crust charity fundraiser. They, of course, know what's coming when the dom unbuttons his pants and releases his gargantuan penis from its leather prison. (He's fully erect--a true master of his craft, I guess.) But Danny has no idea what's coming until the dom grabs his hips, lines up with his hole, and rams home--all in one liquid motion.

Danny squeals like a stuck pig, much to the crowd's delight. His face is contorted with either pleasure or pain--maybe both--as the dom pounds into him again and again, shaking his whole body like a rag doll.

I'd like to think I'm above all this, somehow, but to my horror I am aware of my dick stirring to attention as the show goes on. It doesn't help that I've discovered, quite on accident, that if I twist my hips just slightly, the dildo rubs tantalizingly against my prostrate.

"Enjoying yourself?" Derek asks in an undertone. Goddammit, how does he always know?

"No," I reply, with a touch of petulance.

"Mmm," he murmurs neutrally, but I can tell from his faint smile that he knows better. He picks up his pen and taps it against the notecard. "Maybe some charity will cheer you up. What do you think? What would you hope was coming next, if it was you up there?"

He traces the tip of the pen along the edge of my jaw, and I shiver. I'm not sure if it's from the featherlight sensation or the thought of being the one strapped up there, helpless and vulnerable, subject to the lurid whims of the mob. Or maybe it's from the burn of his steady gaze on my face.

I take a slow, deep breath, trying to bring myself under control.

"How about an orgasm?" I say dryly.

I expect him to laugh at the absurdity or punish me for being a smartass, but he only taps the pen a few more times on the notecard in thought, and then makes his selection and signs his name at the bottom. I catch a glimpse of the menu as he hands it off to a passing waiter. "Orgasm" is the last option on the list. The price is $10,000.

I sputter in shock. All I can think is that amount of money would cover nearly a year's worth of my rent, and he just signed it away without a second thought.

"Are you insane?" I whisper.

"What was that, Jack?" His tone is deceptively light, as he trails the pen along my cheekbone. I'm not fooled.

"I mean, thank you, Mr. Harrow."

He smirks at me.

"How's your little boy pussy? Not so tight anymore?"

I cringe at the edge of mockery to the words but tell myself not to take the bait.

"Fine, sir," I say, trying to inject subservience into my voice. I guess it works. At any rate, he doesn't scold me or stab me with the pen.

On the stage, the dom is finishing up the latest paddling that has been purchased for Danny. In the mirror, it's clear that Danny's buttocks are bright red, practically glowing. There are tears streaking down his face from behind the blindfold and his narrow chest is heaving.

The dom replaces the paddle and accepts Derek's card from the waiter. He reads it and nods, his expression undecipherable thanks to his mask.

Danny flinches and yelps at the sudden touch to his abused cock, no doubt expecting something terrible. He sags in his restraints, perhaps overcome with relief, as the dom merely strokes him, slowly at first, then faster, then slowing down again, drawing it out for the audience's entertainment.

Danny pumps his hips wantonly into the hand, letting out a little cry of despair when it disappears. But the dom is only moving down to his tight ball sac, bouncing them playfully between his fingers. Guests laugh at the sounds Danny is making. He's moaning like a bitch in heat, occasionally interspersed with sweet, pleading little syllables--not quite words.

My own cock is definitely rising to the occasion, much to my dismay, because as Danny is finally allowed to thrust into the dom's hand and explode in blissful release, I know there is no such release coming for me.

I glance sideways at Derek. He's watching the $10,000 display, but with a faraway look in his eye, like his mind is miles away. There's a faint line of a frown etched between his dark brows.

Danny has barely come down from the high of his orgasm when he's subjected to the next menu item. The dom unbuckles his wrist restraints, letting Danny fall to his knees with a soft groan. His ankles are still stretched wide on either side of the frame, so the position is awkward, not that his comfort matters. The dom tangles his fingers into Danny's hair and guides his mouth forward. As soon as Danny's lips brush against the fleshy cock, he obediently opens wide and slurps the mushroom head into his mouth, his cheeks bulging and hollowing as he does his best to suck. After a few seconds, he lifts his trembling hands and strokes at the shaft. For a while, the dom is content to let him do his work, but then he fists Danny's hair and forces the boy deeper onto his member. Danny lasts a couple seconds before he starts to gag. The dom lets him up for the gasp of air, but then immediately feeds his length back down the boy's throat.

Danny gags again, but the dom keeps pushing. It seems impossible for Danny to take the whole thing, but soon his nose is pressed into the dom's pubic hair with the huge, dangling balls slapping against his chin. The bulging shape of the shaft is visible inside his slim throat.

There's a rare hush in the room, as if everyone is holding their breath with Danny. He lasts for almost a minute--though to him it probably felt like an eternity--before he tries to pull off, to free his air passage. The dom flexes his grip and holds him steady. A gleeful twitter races through the guests. Danny lasts another few seconds before he starts to freak out, pushing at the dom's powerful thighs and making small, panicked noises that reverberate in his chest.

I'm beginning to wonder if he's going to pass out, but I guess the dom knows what he's doing, because he pulls him off abruptly. Danny gasps in wild breaths, a string of saliva trailing from the cockhead to his lips. Only a few heartbeats pass before the dom takes control again, this time launching into a brutal face-fucking section. The crowd expresses its robust approval. The guests have been getting progressively more drunk as the night goes on, and some are even shouting for the dom to fuck that slut harder and stuff that sweet little mouth-pussy good.

I can't help but think back to that first night on my knees in Derek's office, when he gave me my first taste of cock. I remember the horrible, wonderful intensity of his gaze on me afterwards, as I masturbated in a frenzy and came all over myself like a cheap whore.

Finally the dom finishes, pumping his seed down the boy's throat, into his mouth, and then the last couple spurts across his face and chest. The guests cheer like their team just scored a winning point.

My attention has been drawn inexorably back to Derek, whose contemplative frown has deepened while he stares down at the second notecard he was handed. He seems to arrive at some sort of decision and fills out the card with a few pen strokes. He passes it to a waiter before I can see his selection.

I follow the waiter's progress to the stage with some interest. Danny has been locked back into his wrist restraints. He's sagging limply now, an utter mess of sweat, tears, and cum. His entire body is crisscrossed with pink and red marks from the various whips and paddles that he's endured. I wonder how much more he'll be forced to take. I wonder how much more he can take.

Derek's second card has been handed off to the dom, who reads it and then heads to the table to grab whatever instrument of torture had been purchased. When I see what it is, my heart skips a beat. A cane.

My gaze snaps to Derek. I don't know what I'm expecting to find on his face, but I find nothing at all. His eyes are on the stage, but his expression is blank as stone. He's completely still, other than the tap, tap, tapping of his fingers on the arm of the chair.

I watch as the dom takes the cane and, surprisingly, runs it gently across Danny's back. The boy's spine arches at the contact, and I can tell from the guttural moan he emits that he knows exactly what's coming next. At first I think the dom was taking pity on him by ruining the surprise, but then I realize it's merely a new way to tease him. Danny is hyper-focused, every muscle tense, as he waits for the first blow. The dom swings the cane, letting it whistle through the air before stopping just short of Danny's buttocks. The crowd laughs as Danny yelps and jerks in anticipation for a hit that doesn't come. The dom toys with him for a bit longer, before finally landing the first snapping blow. Danny howls.

I look back at Derek, but his stony exterior remains uncracked, even as Danny wails with each staccato strike on his ass and thighs. I remember the low murmur of his voice in my ear when he told me that his father had used a cane on him when he was a kid. Whenever he thought I deserved it--which was more often than not.

That wasn't even the worst of his father's sins that he told me that night. But it sticks in my head just the same, summoned by the cracking of the cane against Danny's tender young body. I can hear him begging now, stuttering pleas for it to stop--it's the first time he's broken all night.

I wonder how many blows Derek bought. The dom shows no signs of slowing down. Even the crowd has fallen silent, as if entranced by the raw reality of the boy's pain.

"Cr--cricket!" Danny screams suddenly.

I wonder if I misheard him. The dom stops mid-swing and lowers the cane. Danny hangs by his wrists, his chin against his heaving chest, his sobs coming in shuddering waves. There's a sudden flurry of activity. The dom unbuckles his restraints--more carefully than before, catching Danny with one strong arm so that he doesn't fall to the ground. The blindfold is removed. Someone appears with a blanket and bundles him into it. The dom scoops him up, cradling him like a baby, and carries him off the stage.

"Cricket" is a safe word, I realize. He used his safe word.

Gina is headed back to the stage, pausing to give Danny a kiss on the forehead like he's a child and whispering something in his ear, before gesturing for the dom to carry him out of the room. Far from seeming put out, she's beaming with pride.