Upward Ambition Ch. 08

Just as I think I might be able to weather this, he swallows me down to the root. As his wet, tight throat massages my cock, I start to tremble all over. The strain of keeping myself in check burns deep in all my muscles, but the ache isn't enough to halt the pleasure that is rapidly building to a crescendo.

"Please," I beg. "I can't--I can't stop--please."

He draws back to the head. His eyes meet mine, glinting bright with his own desire, and I think he's going to pull off and tell me I can come. Instead, he deepthroats me again. I cry out like he's wounded me, but the only attack is the euphoric onslaught as he pistons up and down, no hint of a gag reflex, no hint of slowing down. He's sucking me off, but he's still the one who is undeniably in control.

I open my mouth to plead again, but no sound comes out. I'm barreling toward orgasm with no way to slow down. In desperation, my hands fly down to push him off, because surely the punishment of coming--and into his mouth--would be worse than the punishment for breaking position.

Before I can touch him, his own hands shoot up and lock around my wrists in an iron grip, imprisoning them at my sides. I cry out again, this time with the force of my release. My hips buck as I spurt into the warmth of his cruel, cruel mouth. Bliss washes over me, and tears pool in my eyes.

Slowly, he pulls away from my spent cock. Aftershocks of pleasure quake through me but are chased by the first slivers of fear, burrowing into my skin. He crawls back up my body, keeping my wrists in his grasp until he returns them to their position above my head. Then he clamps a hand around my jaw and pries my mouth open. I think he's going to kiss me again, but instead he spits my own cum into my mouth.

I sputter a little but manage to swallow. His smirk fills my vision.

"You did that on purpose," I accuse in a thick voice as tears spill down my temples.

"I can't be blamed for your lack of self-control, whore." He swings his leg over me to slide off the bed. My chest hitches repeatedly with tiny, suppressed sobs, while he digs around for something in the bedside drawer. When I see what he's retrieved, I shake my head pleadingly, even though I know it's no use. His wolfish grin is the last thing I see before he secures the blindfold over my eyes and plunges me into darkness.

Almost immediately, my other senses go into overdrive, hopped up on adrenaline and dreadful anticipation. I strain to listen past my own pounding pulse, but I can't hear him at all. On the plush carpet, I know his footfalls will be silent. He could be anywhere now, doing anything.

Somewhere, in the furthest recesses of my mind, I register that I'm not actually chained to this bed by anything but his word. I could get up at any point and run out of here.

But I won't.

"For your punishment, you won't get the privilege of restraints," he says.

I'm not entirely sure what he means, referring to restraints as a "privilege." But it's obvious now that knowing I won't just get up and run, knowing I'm so completely under his control, is the main source of his pleasure tonight.

Part of me wishes sorely to disappoint him, but I know that's not going to happen. Where would I even go? I have no phone, no car. Could I even get out of the house or would the fancy security system have it locked up tight? I wouldn't be surprised if Derek even had hounds somewhere he could unleash to hunt me down.

I'm aware that my thoughts are ranging toward the hysterical. I try to calm myself down, but it proves impossible, when I don't know what form my punishment is going to take. Did he get the idea for the blindfold from Danny's show, I wonder? Did he enjoy watching the boy dangle in suspense as to whether the next second would bring a flogger on his tits, or a cock in his pussy, or a cane on his ass?

Is he going to cane me?

I hold my breath, listening frantically for any sound, positive that at any moment I'll hear the whistle of the cane coming down on me. Still, there is nothing. My blindfold is already damp with my tears.

"Please," I whisper. I feel like I've used that word more times during my tenure as Derek's assistant than in the rest of my life combined. "I'm sorry. I'll do better. You don't have to--"

I don't get to finish my pointless pleas before he shoves something into my mouth. I taste leather and sweat and the saltiness of pre-cum. My thong. I let out a muffled sound of despair through the gag.

"You will do better, Jack," he says. He pats my cheek, and I flinch at the contact, coming as it does out of darkness. "That's what the punishment is for. To teach you."

No, it's not, I think bitterly. It's so you can get your rocks off on my pain, you sick fuck.

I guess being gagged, when there's no hope of accidentally speaking my thoughts aloud, gives me more freedom in my own head to hate him.

And yet still, still, I just lie there and take it. Guess I'm a sick fuck too.

I hear a sharp scratch of sound, but I can't quite place it, at least until I hear the tiny whoosh and smell a whisp of smoke. He just lit a match. I squirm, horrified at the thought of fire entering the equation now. I hear a small hiss of flame--catching a wick, I think--and I relax marginally. He's lighting a candle. He blows out the match and the smell of smoke briefly intensifies, before fading away. I'd never realized before how much my other senses could fill in, when my eyes were out of commission.

The thought of Derek lighting a candle to set the mood before he clamps me or canes me or whatever else he's planning on doing makes another hysterical laugh bubble in my chest, but I manage to swallow it down.

"You know," he says, almost thoughtfully, as he trails a finger down my sternum, "maybe I should have left that dildo in your ass. You're much better behaved when your little boy pussy is stuffed full."

I offer a muffled disagreement that he ignores, unsurprisingly.

"You enjoy having your ass spanked too much for it to be a real punishment. Maybe I should have taken Mr. Foley up on his offer. I still have his business card here."

It takes me a couple seconds of hazy searching through my memory to place the name. Mr. Foley, the perverted old man at the charity fundraiser who so relished the idea of fisting me like a puppet. I recall the sensation of his clammy hand rubbing my back and shiver.

Derek's hand, warm and possessive, trails down my body to my inner thigh, where the freshly shaved skin explodes into goosebumps at his touch.

"I could sit back and relax with a drink while he has his way with you," Derek goes on, his voice barely a murmur above my heart pounding in my ears. "While he fills your soft, pink mouth with his wrinkly old balls, while he stretches your tight little pussy with his bony fingers, while he defiles every inch of your smooth young skin with his sagging impotence. Is that the sort of punishment you need, Jack?"

I shake my head in a mute, desperate no, even though I'm fairly certain he's just using the filthy talk to torment me while he gets off. While he was speaking, his one hand never stopped its luxurious journey along my inner thigh, over my trembling pelvis, and across my seizing abdominal muscles, but from the blackness of the blindfold I heard the distinct sound of a zipper and the rhythmic fap, fap, fap of him masturbating. He said before that he didn't like to share his toys, and that tracks 100% with everything I know about him. Selfish, arrogant, cynical only child with enough control and daddy issues to keep a team of therapists employed for life.

At work, he pretends to be uninterested in my existence, except when he wants to punish me or use me to get his rocks off, but I haven't forgotten that this entire night was sparked by him witnessing my harmless flirting with Penny. Perhaps jealousy is too strong a word, but he was far from uninterested. It was him who had shown up at my door. Not the other way around.

I cling to that tiny measure of power, irrelevant as it feels at the moment, as I lay here with my wrists bound by nothing overhead, blindfolded, and gagged with my own thong, while Derek uses my helpless submission as his personal porno.

"Or maybe I'll ask Gina to pencil you in for a special session," he says, his voice growing ragged with increasing arousal. Fap, fap, fap. "She is an artist with Japanese rope bondage, and she does her boys up beautifully in a 69 position for an hour at a time, to see who can make the other cum the most. Then the loser gets strung up with weights stretching his balls while Gina pounds him with a strap-on the size of a man's forearm."

Derek tugs suggestively on my scrotum, then burrows his fingers underneath to trace around my sore pucker. I can't help the muffled moan that escapes at the memory of the monster dildo raping me so thoroughly.

"Is that what you want, slut?" Derek's whiskey-smoke breath tickles my ear. "You want to get your lips around Danny's throbbing little prick and see which of you is the better cocksucker?"

While the thought is infinitely preferable to Mr. Foley's ministrations, I know better than to admit that, and I shake my head again. A ghost of a laugh from Derek.

"Liar. I watched you tonight. You couldn't take your eyes off him up there on that stage, all hot and humiliated and helpless. Did you want to be the one sticking your cock in him or did you want to take his place?"

It's a question that I'm glad I don't have to answer--I'm not even sure if I know the answer. It's obvious by now that Derek is just winding me up, taking his time to delight in my vulnerability. I breath in sharply through my nose as he gives my soft shaft a tender stroke, like he's coaxing a shy animal out to play. Even though I'm exhausted and overstimulated from the last orgasm, my traitorous penis stirs with interest at his touch, earning another dark chuckle from him. My cheeks flare with hot embarrassment, even though you'd think I'd be immune to that by now.

I expect him to climax at any second or remove my gag so that I can finish the job for him, but he seems to have abandoned his own pleasure for now, no doubt to focus more entirely on my pain. He leaves my cock alone and pats my crossed wrists instead.

"If you move, this will be much worse for you," he says. I respond with a sound that's meant to be an acknowledgement but instead comes out like a pathetic whimper. I guess some naïve part of me hoped that the threats of degradation were my punishment, but that was obviously just the preamble for the real show.

I hold my breath, trying to listen for the sound of him retrieving a belt or cane, but he doesn't leave my side. I hear a slight scraping sound, like glass on wood, then silence for a few terrible seconds. Then a drop of pure, molten pain hits the center of my stomach. The burning sensation explodes through my nerve endings in one, white-hot second, and then it cools. I'm heaving jagged breaths through my nose and every muscle in my body is taut with primal panic, but I've somehow managed to keep my arms in place over my head.

The wax from the candle, my jumbled brain manages to deduce. He's dripping hot wax on me.

No sooner does the thought crystallize than another searing droplet hits my unprotected skin, this time on my thigh. I barely have time to adjust to the shock of it before another drop of liquid fire lands squarely on my belly button. I cry into the gag, more to release my pent-up energy than anything, as I struggle to keep myself still beneath the onslaught, to keep my hands pressed into the mattress above my head. I understand now what he meant by restraints being a privilege. The strain of keeping my own body in check is almost more agonizing than the hot wax peppering my skin. I never thought I'd wish to be strapped down, but right now it would be a mercy.

Derek remains merciless as ever as he continues my punishment. There's no pattern or rhythm to the excruciating splashes of pain. They assault me from the darkness, sometimes half a dozen in succession, up my inner arm or down my torso, or sometimes with long, unbearable stretches of time between them, wherein I squirm and whimper, trying to prepare myself for where the next one might land.

The first one to land on my nipple draws a shriek from me, and I choke on my own spit. I brace myself, expecting the other nipple to be the next target, but instead I'm surprised by a sting in my armpit, which is somehow equally sensitive. Derek never says a word, but I can imagine the cruel curve of his lips, the ruthless gleam in his gray eyes while he contemplates the next spot.

After a while, I'm finally able to adjust to the pain, and other than a small jolt whenever he hits a new, untouched area of skin, I am able to keep my composure. Stupid of me to think that means the punishment will come to an end soon.

When the first drop stings the thin skin just above the base of my shaft, my entire body seizes up with a fresh, dawning horror. I swear I can hear his smirk as another drop lands beside the first and my chest starts to heave with dreadful anticipation.

The next stab of pain is in the crook of my elbow and then on my collarbone, and I start to relax. That's when he pours a line of scalding wax on my cock from root to head.

I howl into the leather, my fists clenching so violently in an attempt to hold my position that I think my fingernails must have drawn blood from my palms. The wax dries quickly, leaving behind only a phantom heat on my poor penis, and I think the worst must be over. Then, very carefully and deliberately, Derek lifts my abused shaft away, exposing my ball sac.

I start to sob before the wax even lands. My vision behind my closed eyelids blooms red with anguish at the tiniest dribble of white-hot liquid on the hyper-delicate skin of my scrotum. I beg him to stop, but between my tears and the gag, my words are nothing but shapeless blubbering. I guess now that he's reached the main event, he sees no reason to tease me further, and with slow, brutal precision he covers every inch of my balls with hot wax.

I scream into the soaked leather because there's nothing else I can do. It never occurs to me to lower my arms and shield myself or push him away--that's how entirely he has me under his control.

While the wax on my sac rapidly cools, he begins to stroke my cock with gentle urgency. This time, to my bleary satisfaction, it does not respond to his touch and remains limp. There, you sick fuck, I think with strange jubilation. I'm not as much of a pain whore as you thought.

As if reading my mind, he tweaks one of my sore nipples through its wax coating. My cock jumps as if on a string. Still rolling my sensitive nub between thumb and forefinger, he takes the head of my penis into the slick warmth of his mouth and suckles with a masterful skill that sends blood surging into my shaft. My tortured balls begin to tighten, very much against my will. I'm terrified that he's going to force me to come again so he can start the punishment all over, but he releases me well before it reaches that point.

Derek turns his attention back to my scrotum, peeling away the dried wax with excruciating patience. He reminds me of a careless child, peeling the wings off flies to satisfy his morbid curiosity about the anatomy of weaker creatures. His extended silence has become a punishment in its own right, barring me from even the most surface level of his thoughts.

The cool air bathing my scalded skin is both gratifying and uncomfortable. My mostly hard cock does not flag, much to Derek's delight I'm sure, as he gives it a humiliating little pat.

"Have you learned your lesson yet, Jack?" he asks, and the sound of his voice is like a light in the darkness.

I nod vehemently and let out a desperate whimper, half because I can't help it and half because I know how much he likes it.

"And what lesson is that?" He pulls the thong from my mouth.

The sudden freedom to speak after being trapped in my own head for so long shocks me, and my mind freezes so entirely I'm not sure I can even remember my own birthday.

"Hmm, that's what I thought," Derek says, unimpressed. He shoves the damp wad of leather back into my mouth.

"Wait!" I beg, but it's garbled by the gag.

With my hard cock now conveniently risen against my belly, Derek has easy access to my balls for another round of wax. It's worse the second time, scalding my already scalded skin, and I wonder if I'm going to have to go to the hospital after this and explain to a judgmental nurse how exactly I burned a layer of skin off my scrotum.

I'm crying so hard by the time he rips out the gag again that I can barely choke out the words, but I'm fueled by panic and desperation.

"Good sluts don't come without permission," I blubber in a mucus-thick voice, before he can even repeat the question. "I was a bad slut, but I'll be good. I promise, I'll be good."

A year ago, I never could have even imagined those words passing my lips, but right now I mean them with every fiber of my being.

He is quiet for a long moment, considering. I want to hold my breath, but I'm hiccupping with sobs. At last, I hear him blow and smell the telltale whiff of smoke in the air as the candle goes out. My body melts into the mattress in relief.

He pulls the blindfold off my face, and I blink rapidly. At some point he turned off the overhead light, leaving us only in the warm yellow glow of the bedside lamp, but it's still momentarily blinding to me.

I'm too frightened to look down at the wax-splattered Jackson Pollock canvas that is my body, and he hasn't given me permission to move my arms, so all I can do is stare at him in meek surrender. His trousers are slung lower than before, his magnificent cock rising free from his black boxers. He hasn't come in all this time, as always the epitome of self-control.

"Roll onto your stomach," he orders, pushing down his pants and undergarments and stepping free of them, so that for a glorious moment I am able to drink in the full, naked beauty of him, the defined ridges and shadows of his toned muscles, the nest of dark pubic hair from which his girthy length protrudes proudly, the powerful weight of his balls--so different from my own soft body, now hairless as a boy's, my own modest member and reddened, thoroughly chastised balls. Derek Harrow is the peak of masculinity. Everything I am not.

I shake myself free from my own lascivious reverie and obey his command. I hiss through my teeth at the friction of the coverlet on my tenderized skin. I keep my hands in place above my head, content to wait quietly for his next command--until he climbs onto the bed between my legs, pushing them roughly apart, and suddenly my sore, abused asshole is on full display.

My hard-earned lesson about being a good slut flies out of my head, replaced by the awful notion of his giant cock pounding into my stretched and aching pussy. I thought for sure he would leave it alone, after the trauma of the monster dildo followed by the fucking at the charity fundraiser. It's too much. I can't take it.

"Wait, please, not there," I plead, trying to close my legs and tuck them beneath me. I keep my arms still, but crane my neck to look over my shoulder, certain that he'll be able to see in my expression how unreasonable it is to expect this of me, after all I've been through tonight. "I'm too sore. Let me suck you instead. I'll do anything else. Just not there, not tonight, please."

His eyes are narrowed slightly as he studies me, and for a brief second, I think I've convinced him. He does not force my legs back open and instead slides forward to straddle my waist, pushing my head down into the pillow. I can feel the warm weight of his balls against the small of my back.