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Ruined Tom Ford Stilettos

Ruined Tom Ford Stilettos

by shinycrazydi
20 min read
4.77 (1500 views)
adultfiction

I'm a 'finance girl' I always have been. Growing up poor seems to go one of two ways, you either remain poor, shackled down by the inherited poverty, the intergenerational destitution, & learn ways to 'get by' & 'make do' until you eventually die, maybe only slightly better (or worse) off than your parents... or you take the second way, it's rare but it happens.

I suppose we were the Idaho flavor of 'white trash' (or as close as you get). I was the middle child, with two older brothers & two younger sisters. There were rumors my eldest brother wasn't fathered by Dad. Perhaps there's some truth in it, he looked nothing like the rest of us. Mom used to say he took after her, but he didn't. Not much. I wished that the rumors were about me, how reassuring it would be to imagine that I only half-belonged to the people around me, who could barely look after themselves & relied too heavily on me to look after the youngest kids.

Mom & Dad were both alcoholics, both big smokers, both always fighting. Mom was 'morbidly obese' (an Indian-American volunteer clinic doctor had told her so before she'd called him the N-word). Dad was a real bastard. Violent & resentful. Prone to conspiracy theories & weeping before he'd pass out. I recently saw a new photo of my youngest sister & it's sad to say, she's the spitting image of Mom now. Red-faced, tired eyes, wearing blouses that were more like loose tents, no attempt at any tailoring. Batwing sleeves to hide sagging upper arms.

Hopefully Lisa doesn't take exactly after Mom. Mom died a few years ago from diabetic complications. Dad phoned, for the first time in years. Not to talk about Mom, or even tell me she'd died, but to demand $30,000 'for the funeral'. I blocked his number. But I directly paid a funeral home in their town for a service & headstone, made sure it was non-refundable, texted Lisa the details so she knew who to call.

I can't remember the exact moment my plan started to formulate, perhaps from birth. I remember the embarrassment, how I didn't want to invite anyone to our house (we were barely covering mortgage payments on it) with its tobacco-stink, the broken furniture & empty fridge, Mom's hoarded old mail-order catalogues stacked against every wall... I was constantly on guard, trying to prevent people from learning who my family was, where I came from. I became a spy, a mimic, trying to learn what seemed like a foreign culture from the other girls in my years, the ones who looked clean, looked like they had money.

I spent so much energy on my appearance, I was constantly dieting, constantly weighing myself. Instead of eating lunch I'd watch YouTube tutorials in the library, using their free internet (ours always seemed to be disconnected) & learn how to make cheap (or shoplifted) makeup look more expensive when I applied it. I'd learn how to do my own nails (less is more, even now with my weekly gels, I prefer a simple oval manicure with either beige, or something from the reds). I found ways to make sure I looked as 'finished' as possible, always checking my reflection, always with a nail file & comb at hand, checking my lipstick. I learned how to walk, how to talk, how to gesture.

When I wasn't perfecting my appearance I was studying, I paid attention in school. I was fastidious. I knew I had to get to college & there was no way my family could afford it. I knew I'd have to apply for financial aid, I'd have to apply for scholarships. Cut to: eight years later & I had my MAcc, I'd been climbing the ladder in the private sector, had changed my last name & I was known to be 'one to watch'. It was a man's world but Hell, I was so driven, & I knew how to use what I had.

What I had was a pragmatic heart (I've been accused of being 'cold' more than once), especially after I'd had my heart broken in my first year & it had almost derailed my academic plans. I had a sharp brain, razor tongue. I had a formidable botox-assisted resting bitch face, an incredible wardrobe with the type of clothes that signal wealth & taste, nothing flashy, nothing gaudy, but nothing that wasn't of the very best, most exclusive, most expensive quality. Even my 'lounging clothes' were finely woven French linens & cashmere pieces.

I had a Peloton & Pilates toned body & the most natural-feeling & subtly full & perky tits money could buy. You wouldn't know they weren't 'real' even if you spent a whole night examining them. My surgeon's a genius. A Goddamn genius. My eating disorder evolved into small meals of leafy greens & agave-sweetened smoothies. I can tell you without looking, the fat, salt & carbohydrate content of 90% of whatever's in your pantry.

My grooming schedule takes up a lot of my assistant's time coordinating, the waxing sessions, the conditioning hair masks & coloring, the mani-pedis, the lip-fillers, my asshole bleaching, spray-tanning (no lines, no streaks), full body scrubs & seaweed wraps... the whole works, I never take a season off. One of the first things I spent money on, real money, was getting a flawless set of high quality veneers. Any imperfection in a person's teeth is a dead giveaway they're tainted poor. Once a week Sephora delivers a new carton of the serums & cosmetics I use daily. The trick is to make it look all natural, effortless. Don't get streaks in your hair, unless they're incredibly subtle. Don't wear a lot of jewelry, wear a few pieces, but make sure it's real, make sure it's expensive. Don't follow trends too easily: old money doesn't do that. You want to look 'timeless'. You want to look like you're above everything else.

Beauty is powerful. Sexual attraction is power. Confidence (especially if you can find some real confidence) is power. Youth is power. (As long as you're not actually that young & you've learned how to use the illusion of it). I had started small, not really understanding how to wield the power to my best advantage. Blowing my Econ professor during his 'open office hours,' or letting him fuck me in the ass to catch up on my course load after my first heartbreaking relationship ended (the boy I'd been seeing left me for my ex best friend).

I started escorting under the name 'Evelyn' in my second year. It had seemed to be an easy way to make money, going on dates that didn't have to end in sex. I soon learned, they all end in sex, no matter what the agency tells you. Men aren't parting with $1,500 for a date that only offers conversation. Within the span of 4 weeks my sexual repertoire accelerated to soaring heights. I'd been taught some of it willingly, some unwillingly, but, I figured, it had still been an education of sorts. At least the experience had been valuable in reiterating how important control is. I worked with that agency for nearly four years, while I completed college & even my first year in the workforce.

Our team was competitive & I was the only woman gunning for one of the few leadership roles in the accounting team. I worked my ASS off. I was without a doubt more qualified for the position than all of the slimy, over-confident grown-frat-boys. My record was outstanding, within my first year there my predictions & nose for investment had returned millions in new profit vectors. I cultivated excellent relationships with clients & investors, I worked well with other departments, I never took a sick day. I proved myself invaluable over the next few years.

But I was being talked over in meetings, dudebros were taking credit for MY insights, MY ideas, MY business contacts. Even though I was out-performing them on paper, they would just high five each other, they'd get courtside tickets from their daddies to pass on to the big bosses, they'd take the upper levels to strip clubs & I was being excluded. Deals were being made that I was unaware of. The final straw came when I learned that one of my projects, an exclusive investment opportunity that promised a hefty profit on maturity, one I'd spent countless valuable weeks working on negotiating & getting the sign-off from each board member & consulting fees & research & was everything but signed on the dotted line - that THAT deal was going to be fridged in favor of one of the overgrown privileged bonehead's half-baked ideas. Fuming, I inquired how the decision had come about, why I hadn't been in the room when it had been discussed. & sure enough, I was brushed off, my concerns were ignored, the choice had been made at one of their little boy's club evenings.

For the rest of the day I was livid. I locked the door to my office & screamed into a throw pillow (this wasn't unusual in our stressful industry, the men can kick furniture & curse & waggle fingers, but if you're an angry woman, try to hide it, take it from me). Instead of working, I sat & rolled a pencil between my fingers & gazed out the 9th floor window at the city. I'd already made a decision, it was just a matter of how to approach it. It was 7pm when most people finally went home. I knew Mr Asprey would be working extra late that night, I knew his workload as well as anyone. So I caught the lift to the 16th. I stormed past his exhausted personal secretary, ignored her as she meekly called out to me & let myself right into his beautiful, masculine, corner office, with the stately marble desk.

He was caught by surprise, something I hadn't seen from him before, I was already off to a good start, I thought. He cleared his throat & pressed the intercom "Cora - " he began.

I pointedly flicked the lock on his door, it made a resounding metallic thud. I looked at him like a snake hypnotizing its prey.

"Uh... nevermind Cora." finished Asprey. "Jules, if this is about the - " but I had crossed his office in four quick strides, I slid his laptop & papers to one side & sat on the stone surface. We were closer than we'd ever been to each other, I had reapplied my YSL fragrance about half an hour ago, it would be warm & intoxicating by then. He was staring at my tits, at the glimpse of gossamer lace that peeked through the lightweight silk neckline, the suggestion of the balconette bra I wore underneath. Looking him right in the eye I used my little finger to pull the neckline open, flashing him a clearer view at the flawless skin, the delicate black lace.

His breathing was heavy, God, I thought, I hope his heart's healthy enough for this. He raised his hands to the tiny buttons down the front of my shirt, the gold band on his left hand flashing at me as he did. I caught his wrists, gently pushed his hands away. He looked a little put out but I knew I had him & he pressed the intercom again. "Cora?" he asked.

"Is everything OK Mr Asprey?"

"You may as well go home now."

"No." I said, shaking my head "Cora stays."

He hesitated. I could see he was confused. Good. I glared at him, impatiently drummed my nails on his desk. "Cora stays," I repeated firmly.

After some kind of internal debate with himself, he pressed the buzzer again "On second thought, I might need you after all. Stick around."

"OK Mr Asprey." Poor Cora, she sounded disappointed. But getting him to obey me was important if I wanted this to work.

I slowly began to pull up the hem of the pencil skirt I wore, sliding it over my thighs. He could now get a good view of the suspenders attached to the top of my stockings, the tiny clips & ribbons, the black silk filigree that matched my bra, my long, toned, tanned legs, my naked pussy. I'd removed my panties & checked the suspender belt before I launched my attack & now I was sitting, bare assed on his precious marble furniture. He gasped, I teased him a little with the view, raising the skirt hem a little, so he could see it peeking out, lowering the hem slightly. I slapped his hands away each time he thought about touching me. Finally I let him see it all, he staggered & coughed a little when I pulled the skirt high enough that he could see the vertical piercing of my clit-hood. I spread my legs & my skirt rode all the way up past my hips, the straps of the suspenders bowing a little.

I pivoted slightly, & stretched my right leg onto his desk, the soles of my stiletto heel on the leather topper, my knee bent. The position opened my hairless cunt wider, & I took two fingers & squeezed the lips, the little labia together, tweaked the dainty barbell against my clit, before I pulled my fingers open & spread the lips apart. The room was so silent I could hear the little wet 'kiss' sound, that little moist 'suck', as my wet vagina opened up. I could feel the juices peeling apart, trying to stick together like an overripe peach you pulled open at the end of summer. I rolled my neck a little so my hair fell loose.

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I removed my now wet fingers & brought them to his face, made him smell them, suck them. I told him "What are you waiting for, Henry? Get down there & eat it."

He paused & his eyes met mine for the first real time, in his Saville Row suit, with his bald head, he still looked like a scared, slack-jawed little boy, a cartoon turtle. "Hurry up, I'm running out of patience." I urged, putting a growl in my voice.

Of course he did. He knelt & stuck his entire face between my thighs. He tried his best. At first he licked slowly, tentatively, but hungrily, moaning in rapturous abandon as he probed & explored the smooth, fragrantly moistened caves of my vagina. I barked orders at him "faster!" he obeyed "harder on the clit!" obeyed. "Haven't you ever got a woman off before? Have you ever seen a vagina before today?

Jesus, you call this oral? I should've just gone home.

You're pathetic, you're a dog, you worthless, snivelling piece of shit, this is the worst head I've ever received.

I should tell everyone, everyone in the office how useless you are, that you can't even eat pussy without fucking it up."

By then he was crying, crying as he frantically ate my cunt. His dick was out & he was jerking it, fast, energetic, panicked strokes, his hand a blur, I could see he was about to cum & I swung my right leg around, pressed the heel into his shoulder & pushed myself back so his cunninglingus was interrupted.

"You filthy old bitch, who gave you permission to get hard?" I demanded.

He looked up, tears on his smiling face, awestruck. "I... I thought..."

"You thought? Fuck. That's a good one. You stupid, weak loser. Wipe your face."

He sniffed & wiped his tear-streaked face with the arm of his $5000 jacket. I hopped off the desk.

"I'm the boss tonight" I hissed at him. "What did I say?"

"I'm - you're the boss."

"Are you pathetic?"

"Yes."

"Yes what?"

"Um, yes Juliet."

"MISTRESS Juliet" I corrected him. I was circling him, looking him over with disgust, I pinched his bum, pinched his arm, squeezed his old-man tit, opened his mouth as if checking his teeth. I saw him squirming as I looked up & down at his dangling cock. Good, the hard-on was easing slightly. I made him stand up & I slapped it.

He gasped.

I slapped it again.

His cock bobbed & twitched. He was red-faced, puffing hard.

"Do you like that?"

"Yes - Mistress Juliet."

I slapped it again & he moaned.

His dick was bobbing frantically. "You better not fucking cum until I tell you to." I ordered.

He was swaying on his feet, eyes shining, he was having the best day of his life.

"Do you hear me? Don't you dare cum until I give you permission."

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"Yes - Mistress Juliet."

"Good boy."

He looked at me with pleading, wide eyes.

"Undo your belt." I demanded.

He did, his wrinkled hands shaking on the buckle.

"Are you stupid? Pull your pants down. Take them off." I ordered & made a show of rolling my eyes. I undid the buttons on my shirt, removed it. Removed my skirt. I stood there, 5 11' in heels, my long legs spread apart, tantalizing him in my black garter belt, black bra & the silver glint of the delicate barbell at the top of my cunt. The friction of his sloppy pussy eating, combined with the stimulation of that piercing had stiffened my clit & if I put my leg on his wingback chair he'd get a good view of it. 'Maybe next time,' I figured 'if he earns it.'

He'd kicked his trousers, jacket, underwear, shoes & socks off, they lay scattered around him. I considered making him tidy the room up but reminded myself I didn't want to be there all night. He stood there in his shirt, a hopeless picture of need & arousal & embarrassment. I swivelled, crossed at the ankles, bent from my waist & let him get an eye-full of my vulva. I leaned under the desk as I did so, collecting one of his bespoke Italian shoes. When I stood, I slapped it into my hand a few times. With each 'whack' he shivered & I knew I'd guessed right about him.

"Put your hands on the desk, Henry." Nobody called him Henry except his wife, it was deliberate.

He did, bending over with his liver-spotted, sagging white ass sticking out. God, dirty old men were easy. I spanked his buttocks - hard - with his shoe. WHACK.

Ughhhh, he moaned.

WHACK.

He was trembling, his sad little erection was sticking against the front of his desk. His long, deflated balls dangled uselessly. His asshole was tight & pink & twitching.

I reached out a hand, extended my finger, ran a sharp fingernail up his perineum. He almost yelped, twitched so hard there was a smear of pre-cum on the marble.

WHACK.

This went on for some time, I increased the strength of each blow, his dick flopped around. Every now & then I'd lean forward & whisper in his ear.

"You need me."

"Yes Mistress Juliet."

WHACK.

"I'm the best fucking employee you have."

"Yes Mistress Juliet."

WHACK.

"If you start being a good boy, if you start treating me with some RESPECT (WHACK) I'm going to do this again next Wednesday night."

"Please Mistress Juliet, I promise I'll do better."

"But if you disrespect me, if you're a naughty boy, I'll join Mr Albrecht's office instead." WHACK. "I'll take care of everyone BUT you."

"Please don't do that, I'll be better, Juliet, I mean, Mistress."

His ass was red, bright red from the beatings, he would have to sit on an icepack tomorrow. I dropped his shoe, knelt behind him & slid my own shoe off (this would be a damn shame I thought, I wished I hadn't worn such favorites, my poor Tom Fords).

I spat on the heel & eased it into his yielding asshole, pressing his sphincter open in a similar way to how I had my cunt. He clenched a little & I told the good, obedient boy to relax & it entered him. His whole body was shuddering violently, he couldn't hold back he was yelling: "Oh God, Oh God, Oh my God, Oh God, Yes! Yes! Yes! Please! Oh! Please! Yes!"

Using the body of the shoe, I twisted the stiletto heel inside him, slowly, gently, penetrated him more, until his anus kissed the sole, then slowly twisted it in a circle until I knew where it was pressing. The whole time he squealed in delight, his voice almost girlish, he was crying in ecstasy, his face a shining, beatific cherub. He was ascending to heaven, he was melting, he was on fire. He was still trying to plead but it was coming out as strangled squawks, words had abandoned him & he was grunting, oinking, almost braying, practically barking. I whispered that he was a good boy, a brave boy. I pushed the heel in a bit harder, then see-sawed it, finally hitting the spot & I whispered "go ahead" & he ejaculated, ropes of cum shooting onto his desk, onto the carpet, onto his briefcase. When the milking concluded I extracted the heel with a wet 'shlurp' & put it back on.

He was curled in a fetal position on the floor, the tails of his shirt dipping in the puddle of sperm, his little cock like a deflated balloon. He looked like he'd been reborn. I love first-timers. I'd recognised his secret desire to be dominated as early as in my job interview, recognised it in his tightly wound, conservative life, his temper & frustration. Where he indulged in porn & strippers & whores but had been too afraid to ask them for what he really wanted. & I'd seen it immediately. Recognised the weakness & seen its potential. I'd drawn the humiliation out of him, let him know I knew he was weak, & he'd loved every dirty second of it.

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