Pencil Skirt and Heels

J....

She was at once his favorite and most despised financial advisor. C had the book of business he needed and clients who were accustomed to borrowing, but she was regularly an insufferable bitch.

C, the product of a fine family from the Northeast, grew up in the business. U Penn and Wharton Business School educated, she worked under her father and eventually took over the team upon his retirement. Nepotism notwithstanding, C was a closer. She grew the business dramatically, closing more 9-figure-plus families than any other advisory team in the firm. Fantastic with clients, however as her success grew in magnitude so too did her ego and the ruthlessness with which she conducted herself with anyone internal to the firm.

Just beyond 40 years of age, C was physically captivating and knew how to use it. She was of medium height, 5'6", and had curves she knew how to use. She had the hourglass figure virtually all women were jealous of and men salivated over - punctuated by beautifully large natural breasts, delectably curved hips and an ass that defied gravity. Though she'd never admit it, she knew how her favored attire affected clients and internal stakeholders alike. Typically in a pencil skirt, fitted button up blouse and heels never less than 3", although technically professional attire, her often crossed legs drew attention and the curves of her body as she walked demanded admiration.

Situated in an office just down the row from J, she passed his glass front frequently, and it tormented him. J was a high net worth lender and he liked the business results that close proximity provided. She would bark for his presence to discuss one loan ask or another. Her clients regularly needed yacht upgrades or a new jet; financing for a piece of commercial real estate or leverage to fund private equity investment, all of which J efficiently provided to their mutual benefit. He built his yearly bonus on the balance sheets of her clients, and the power imbalance was clear. She noticed his eyes frequently and she knew he needed her more than she needed him.

J was a newly promoted Director within the firm, which reflected a long and successful lending career. His experience within the industry was wide and he was well regarded amongst clients, Management and centers of influence across the many markets for which he had responsibility. In every facet of his life he presented control and fine attention to detail. Liberal and progressive in his perspective. Dominant in regard to his romantic engagements.

And it was this particular dichotomy that began grating on him more and more. He craved her physically, however the power dynamic in her favor became increasingly problematic. It only made him want her more. The prospect of taking her, with or without her cooperation or compliance, took up more and more of his thoughts. It became a distraction when he was sitting across from her in her office - not helping that her desk was a glass top she was incessant in her leg crossing and had the tantalizing habit of dangling high heels from her perfectly shaped feet. Beautiful instep, perfectly shaped arches, and the heels she chose served to highlight these, of course with the sexiest hint of toe cleavage.

The more demanding she got, the more he wanted to fuck her. Every rude interaction he heard in the office made him want to take her more and more violently. Every dismissive look she gave reminded him of his desires to skull fuck those beautifully made and pouty lips. He had incorporated consensual non-consent in his play with submissives he'd toyed with, but this is the first time he'd felt the urge to actually take someone. To actually rip the slit of her skirt to expose those milky white cheeks. To press her face to the glass and unceremoniously shove his cock deep into her pussy in one thrust. His distraction grew and it became all he could think about.

C....

She was used to looks but his looks were different. She knew how her curves affected men and on occasion used cleavage to her advantage. The power her high heeled legs and feet brought her though was intoxicating. She could pick a foot fetish man out from a crowd and these were the most fun. She knew that J was one of these. While he was always professional, he just couldn't help himself when she crossed her legs at her glass desk and he had to take a peek. It was a stroke of genius having the company provided furniture moved out in favor of the glass. It gave her the upper hand in client and internal meetings alike, almost universally.

She'd done business with J for several years now and knew him to be a closer as well. He was good at his job and he represented her and her team well. Increasingly over the last few months though there had been more friction and she was cracking..

She kept the various aspects of her life very siloed. In her corporate life she was the very definition of Type A Boss Bitch - she quite literally owned everyone with whom she worked. At her core though, she yearned to utterly debase herself to a strong and worthy Dominant. The friction with J, she knew, was in the knowledge that he was an experienced Dominant. She knew it. He was too controlled in everything else not to be. He oozed ownership, which intriguingly, must be what had both of them itching. She knew she controlled his bonus, but he was aching to own her asshole.. Her body started responding whenever he was in her office, becoming uncomfortably wet when she smelled his body wash. His closeness showing the sheer magnitude of his size relative to her. He was 6'2" but had a much larger presence. He had impossibly broad shoulders and the width of his back made her bite her lip. He dwarfed her size and she longed for him to gag her on his cock. Put simply, she wanted him to have his way with her.. To use her.. To leave her in the corner cum covered and whimpering - asshole gaping and sore. Pussy and mouth thoroughly used. She struggled to keep up her persona. The loathsome nonchalance with which she regarded everyone else. When in truth she wanted to be his cum bucket, his fuckbag, the thing he used at will.

J...

The unmistakable smell of pussy... In her office. Door closed, confined space. She had grazed by him at the beginning of their meeting and he was partially hard having followed her down the hallway to her office. She was wearing her Louboutin So Kate's today - his favorite - black calfskin with the shiny red bottom. The walk was less than a minute but he was in a trance and didn't realize it until they passed closely in her office. Fitted suit pants and a large cock didn't exactly mix well. Nothing was said, but the tension was at an all time high. Then he smelled her. She was flushed. And in that precise moment, he knew he was going to take her. Maybe he wouldn't have to take her against her will, given her delicious scent, but it was going to happen and it was going to happen soon.

C...

Dressing that morning she had to stop and make herself cum. She had to clear her head. She couldn't have these thoughts when she knew she was meeting with him today. Even after cumming though, she pulled out the Louboutin's she knew made him hard, and walking out the door she paused and took off her panties - hanging them on the key hook as she walked out

She came to get him at their appointed time. Didn't know why, but she did anyway, and relished the feel of his eyes on her ass and legs as she walked down the hallway. What she didn't expect though was feeling him as she held the door when he walked in. Overcome with excitement and no small amount of fear at the thought of what must be a very large cock. She immediately gushed and quickly sat, worried she would be streaming down her leg very quickly!

J...

Leaving her office, J resigned himself to taking her, and he would have her tonight. Smirking to himself at how easy she had made it for him, he made his plan. C drove a black Mercedes G Wagon with vanity plates that read "CSGWAGN" and she parked it on the top floor of their garage, tucked away in the corner to protect it from getting scratched or dented by cars next to it. This obsession would ultimately get her in trouble.

C...

She was finally able to stem the tide of wetness from this close encounter with his cock. It was difficult, but she was able to regain focus and finished the rest of her work day. With little in the way of a social life, C often worked into the early evening on coming prospect pitches, client reviews, or simply catching up on market news. Lights on their floor were often turned off by the time she closed up and left, and where she at one time was nervous walking to the corner of her garage where she parked her baby, she now didn't think twice about the quiet solitude of this part of the garage. She knew the garage had a security guard ten floors below and that it was swipe card controlled. She was safe.. Nose in her phone as she walked through the garage, she was the epitome of what not to do. She didn't unlock her doors as she walked up to her car and she wasn't prepared to immediately enter her car and lock doors. She lingered next to her massive SUV as she walked up, and didn't even register danger when she heard footsteps behind her. It didn't even dawn on her she was in trouble until strong arms interlaced hers and wrenched her off her feet, dragging her backward behind the SUV, between it and the back corner. One arm and a vice grip hand held her arms back behind her and the other clamped down on her mouth before she could scream.. Panic set in, her eyes dilated, she couldn't move. Couldn't see who controlled her, but that scent was familiar.. It was a clean scent of shave cream, starched collar, body wash and lust. He slammed her against the back of her SUV, felt him press his cock against her ass and grind into her. Still frozen in fear, she but whimpered under his control. And in a split second she found herself on the ground face down with him straddling her. This wasn't happening. This couldn't be happening...

J...

So predictable her working hours. He waited until everyone else left, cock nearly at attention this whole time. Anticipating finally taking her. Having her ass. Biting her breasts. Cumming on her face.. When the hour approached that he knew she often left, he quietly packed up and turned off the lights before exiting the office. He took the primary elevator down from their 26th floor office to the lobby, then nodding at the security guard before boarding the parking garage elevator back up to the 10th floor, top floor of the garage. Her obnoxious SUV was the only vehicle within six floors and he knew the solitude and seclusion was his friend tonight. Taking up position behind her vehicle, he waited for his prey, his cock now rigid, salivating in anticipation.

The elevator bell wrung and he heard her high heels approach. Through the windows he could see her lack of awareness and actually chuckled again at how easy she made this for him. She approached and momentarily paused, actually waiting for him to take her. He stepped up and wrapped his arms around hers in the makeshift bondage arm control he'd used on other submissives. Clamping down on her mouth, he felt her lips, relished this control and made short work of putting her face first on the ground, knees on her forearms so she couldn't move. In one move his belt was off with a slap - was that whimper of fear, or?? Regardless, he expertly immobilized her wrists with his belt, freeing his hands, then removed his tie and triple wrapped it around her mouth and tying a gag so she couldn't scream - as if it mattered.

C...

He ripped his belt off and the knowing slap it made caused an involuntary whimper from her and she internally scolded herself. Her most recent Dominant would wear old jeans and a belt when he played with her. Her most favorite was when he would affix her to his bedroom door via wrist cuffs and an anchor. He would use her body to his enjoyment, writing on her, worshiping her restrained body, exploring her holes with tongue fingers and toys, but her favorite moment was hearing that belt being ripped off because she knew he soon would be fucking her. It was involuntary, that physical response, almost Pavlovian, and her pussy gushed.

Commotion behind her, she quickly felt and realized he was wrapping something around her mouth, once, twice, three times... It was a tie - red.. The tag momentarily visible - Hermes.... And in a flash, she saw J squeezing past her with his cock partially hard, that tie, red.. Unmistakable. The familiar smell.. It was J.... J was attacking her. It was J. His beautiful hands on the back of her neck. It is his now massively hard cock grinding into her ass between the fabrics of their clothes. Oh my god, J IS ATTACKING ME. She screamed into the gag and bucked her body but she was completely and utterly controlled.

J...

Isolation and control established, J smiled to himself and relaxed. He took his hand from the back of her neck, unbuttoned his pants and released his straining cock. He stood up, grabbed her pencil skirt by either end of the split that enticingly went up her thighs and ripped it entirely from her body, exposing her bare ass. No panties. Almost like she had prepared to be fucked today. Little did she know what he had in store for her.

Having stared at her ass for years, J dove in. He didn't care that she hadn't showered for almost 12 hours. He bit her ass, buried his tongue in her surprisingly juicy pussy. He tongue fucked her asshole, savoring every inch of her. Still screaming and writhing, C couldn't move. Not able to wait any longer, J moved up and straddled her ass. As if she knew what was coming, C screamed harder and bucked her hips in a futile effort to unseat him. He lined up the large mushroom-head of his cock with her puckered little asshole and pressed in... Her body fought him, but eventually relented and where he would typically be gentle with his submissives, he buried himself balls deep in her. She went rigid and it was as if every molecule of oxygen left her body.

The warmth of her asshole overcame him. He'd dreamed of using her for so long and it was finally here. He pulled out and pressed back in again.. Quickly began fucking her. He grabbed her hair and turned her head slightly and saw that she had gone glassy-eyed. Whatever.. Her ass was incredible. Plump white cheeks spread and he watched his cock impaling her tight little asshole. She'd gone limp and stopped fighting really. She still whimpered and tried to scream occasionally, but her asshole still occasionally clamped down and tried to fight the intrusion. Her arms were still tied behind her. Her mouth still gagged. Her body was his. He looked back and her feet were writhing. One Louboutin was off and the other had slipped off her heel, but her foot was still in it. Her feet showed her pain.. He loved it..

C...

She knew it was coming. He wouldn't fuck her pussy. Her pussy gushed when he bit her. When he dove into her pussy and ass. She wouldn't be able to control moans of pleasure if he actually fucked her pussy and she didn't want him to know she didn't NOT want this to happen. His cock terrified her though and she screamed. She knew he was huge and she knew he wouldn't be polite. He postured up and she knew it was coming. She felt what must have been a HUGE head positioned at her ass and it happened. Searing pain.. And the pleasure of her sub space took over. And she went limp.. And her eyes went glassy.. And she lost track of time. The only thing that existed was her asshole and the massive limb that was impaling her. He was ruining her asshole.. She felt his balls slapping her pussy as he pounded into her. He was relentless as he withdrew his length almost entirely with each thrust. No.. She didn't want this to happen. She can't cum.. Ignore it. But she couldn't. She felt her orgasm building - it wasn't exactly rare that she experience anal orgasm, but it never occurred without any other form of stimulation. And yet, it was coming. Each brutal, uncaring thrust brought her closer. She felt her knees being rubbed raw against the concrete. Her feet and ankles burned, thrashing, trying to crawl from under him.. Closer. Her pussy gushed at the onslaught. Closer - he was using her perfect ass.. And it started - her orgasm crushed her, wave after wave, she screamed into it and pushed back into him, willing her ass to suck him in further. She came violently, massively.. Thankful she was gagged, all she could do was scream... Then went limp and nearly lost consciousness as he used her limp, spent body.

J...

Now pounding her poor little asshole, J grabbed her neck and shoulders and launched his cock deep inside her.. Bludgeoning her. He fucked her harder than he'd fucked anyone before, in any hole.. He picked up speed as he felt his orgasm build, vaguely aware of C going through a fight of her own, body writhing, scrambling to get out from under him, violently thrashing, one final scream then she virtually passed out and went completely limp.. He was near cumming.. Pounding her.. Closer now, he decided in an instant what was next.

One last thrust, and J violently pulled his cock from her, leaving her violated asshole gaping and punished. He quickly moved to her face and grabbed her, dazed, turned her head and presented her face and started cumming heavily. One, two, three large ropes of cum coated her forehead, eyes, nose and mouth. Pulling his cock, he continued to cum and sprayed the last of his cum all over her. Out of breath, he sat back and admired her smug little face, ruined, covered in cum, makeup destroyed, but awkwardly looking content. One last plan to decimate her, he pulled his tie from her head and shoved his cock in her mouth. Holding her by the hair, he pressed his messy cock deep down her throat and felt the last pulses of his orgasm finish, using her mouth and throat to clean his cock. To his surprise, she didn't bite. She didn't wretch.. She just laid there, defeated.

Done using her body, he untied her arms from behind her and they fell limply to her sides. He put his belt back on, tucked his shirt back in and got situated again. J draped his tie over his neck and took one more admiring look at her body. C laid there spent, shoes off, pencil skirt ripped completely off, ass still gaping, cum covered face. Not being able to help himself, J pulled out his phone and took a photo, thinking this was the most beautiful he'd ever seen her.

"See you at the office", J said to her and walked down the ramp one floor to his own silver SUV..

C...

Still holding on to the last moments of her sub space, she felt him exit her asshole and not-unexpectedly moved up and she waited for his cum. Not disappointed, she watched dazed as he covered her face. Seeing it for the first time, she was enthralled at the size of his mushroom head, not caring that cum was getting in her eye. She quietly loved the feel of his cum all over her. And her debasement was complete when she felt her mouth being opened and his cock shoved down her throat. Her gag reflex long since minimized, she let him use her mouth to clean off his cock. He must have been satisfied at being thoroughly cleaned, again vaguely aware that he'd stood up and was dressing himself.

She heard him say something, heard a photo being taken and saw him walk away. "Daddy", she whispered, but he didn't hear her.. She gingerly laid there one by one moving joint after sore joint, trying to reintroduce circulation to her shoulders. She rolled over, now onto her back and for the first time began to feel searing pain in her asshole, reality of her impalement beginning to hit her. She felt the cum on her face, smelled and tasted it. And oddly aware that her pussy was still wet and gushing.

Not confident she could stand, she laid there.. Her phone was right next to her, but for some reason the thought never crossed her mind to call the police or an ambulance. Her right hand absentmindedly touched her pussy. Her left hand reached up and touched her face slightly. The cum. This amount of cum she'd never experienced, and she'd experienced a lot. Her clit was engorged and her breathing deepened. She put a finger in her mouth and tasted his cum. Her other fingers plunged in her sopping wet pussy. She spread more cum around her face. She fucked her pussy with her fingers.. She smelled his cum. And her other hand violently attacked her clit. She laid there, asshole gaping and completely used, half naked, dirty and disgusting; masturbating.. Aggressively. Her second orgasm quickly approached and she screamed at herself internally for the depravity of her actions. She remembered the feel of his cock in her asshole and she came. Hard!