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Lisa - A woman hard to please

Lisa - A woman hard to please

A man's life is made difficult by his female boss
Drew made his way to work that morning, as the bitter November wind blew the few remaining leaves from the poplars that lined the road to his office. Since joining Skintight Cosmetics, Drew had had something of a wake-up call. The realities of the modern world of the make-up industry were that women, generally called the shots and their fat cat employers sat back and reaped the dividends.

Drew joined in the August and was expected to hit the ground running. He had a good CV and had impressed his new boss at his interview. Now, with hindsight, being economical with the truth here and there had been a miscalculation. Lisa, the Senior Sales Executive at Skintight was a hard task master and didn’t accept anything short of a hundred per cent from her team. Drew discovered this to his cost in his first week.

Drew had sent a note to Lisa, outlining customers that met their main stockist criteria. She emailed him back the same day.

‘Drew. Is this meant to be funny? When I receive communication from my staff, I expect to be afforded the courtesy of accurately punctuated and correctly spelled emails. Please take note…


Drew had to re-read his email and found that he had mis-spelt the word separate.

‘Strewth! That’s picky,’ he thought to himself.

The thing was, Lisa wasn’t just an assertive boss, she was also hot. Exceptionally so. She was twenty-nine. She had progressed through the company with her razor sharp intellect, attention to detail and astute business mind. She had impressed her bosses and was promoted to Head of Sales after just one year. She continued to climb the corporate ladder and became a junior Director, eighteen months later.

Drew had read her bio on the company website and it was glowing with testimonials from customers.

Lisa was 5 feet 8, but walked tall in her heels. Her business suits were bespoke and accentuated her cut glass figure. Drew would steal the occasional glance at her amazing ass, whenever she moved through the office, oozing authority. Her breasts were not just ample, but statuesque, owing to her slim waist and child-bearing hips. Not that she had the time for children. She might do, in a few years but she was too focused on her career for now.

Another example of Lisa’s management style revealed itself to Drew in his second week. Lisa appeared next to him, quietly, as she always did. She had an almost stealthy way of popping up next to people’s desks. Drew looked up and she leant against his desk, her long, luxurious hair cascading over one shoulder. Her hair was as intense a strawberry blonde as you could have, without actually making her a redhead.

“When will the sales trends report be ready Drew?” Lisa asked, softly.

Lisa’s voice was feminine, with rounded vowels and a hint of crushed velvet. A little shudder went through Drew’s spine as she spoke.

“Tomorrow morning, I hope.”

“Six o’clock tonight,” she said, quietly but firmly.

“But, I’ve got to do the…”

Lisa looked at Drew with her sapphire blue eyes. They pierced his soul, her looks a heady mixture of beauty and asperity.

“Tonight, six o’clock,” he confirmed, with a gulp.

He eventually completed his task and laid the report on Lisa’s desk at six thirty.

“Sorry it’s a little late."

“Hardly acceptable!” said Lisa. “But as you’re new…” she added.

“OK, well see you tomorrow,” said Drew.

“Indeed you will.”

Drew turned to leave.



“You work out don’t you?”

“A bit, yes. I’m just off to the gym now in fact,” he said, indicating his sports hold all.

“Good. Sound in mind and body.”


“Let’s hope you can pay as much attention to your report-writing as you do your abs!” said Lisa, acerbically.

Drew flinched at the back-handed compliment and left the office. He thought about work and Lisa specifically, that night. Was it just because he was new, or did she show the other staff more respect? She seemed to delight in belittling him and go out of her way to make his life difficult. Yet, no matter how often he complained to himself, he couldn’t get over her beauty; her sheer radiance and sexual charisma. The next day was a Friday, so it was a short day. However, the pile in his inbox appeared to be growing as were Lisa’s demands.

In the middle of the morning, Lisa came over and leant with one hand flat on Drew’s desk. Her perfume was amazing, and had the intensity of a rare purple rose. Drew looked at her, his eyes wandering lustfully, beginning with her ankles, following every contour of her body. Lisa picked up a few shards of pencil sharpenings and let them flutter to the floor.

“What’s this?”

“I sharpened my pencil.”

“I know what it is you dick! I mean why is your desk so filthy.”

Drew looked round, conscious that one of his colleagues would overhear her upbraiding him.

“Look at me when I’m talking to you Drew.”

“I’m sorry.”

“Remember Drew, I’m very near the top of the ladder. You’re barely climbing off the bottom rung. I expect to see my face in your desk on Monday!”

“Yes, I…”

Before Drew could finish his sentence, Lisa had turned away quickly and walked off, leaving him to stare at her amazing butt. He looked at his desk and blew a little dust from the surface. It looked as clean as everyone else’s.

Drew spent the weekend at his girlfriend’s. Being called a dick was beyond the pale as far as he was concerned. He thought about airing his concerns with his girlfriend, but he was wary of appearing meek. Never the less, Lisa’s behaviour was bordering on bullying but he didn’t know what he could do. There was no one to speak up for him, not that anyone would for fear of getting on the wrong side of her. Drew tried to put work to the back of his mind and enjoy his weekend.

Monday came all too soon and saw Drew in a meeting with a few people from the office, Lisa and the Financial Director. There had been a slight dip in Sales in the North West region and a meeting had been called to discuss it. The Director was a mature man with flecks of grey in his hair and his blue-grey eyes twinkled through his spectacles as he looked at Lisa. She was all “Yes Sir” and “No Sir.” Lisa not only had a head for figures but she knew how to fawn when it was needed.

The meeting came round to Drew’s department and he found himself in the spotlight. Suddenly he couldn’t lay his hands on the right report and rifled through his folder, desperately trying to produce it. He felt the glare of the meeting on him and Lisa stood up, snatching the file from his hands.


Drew looked stunned.

“Excuse me?”

“I ask you to do one simple thing and you fuck it up!”

The Director looked at Drew over his glasses, and there were awkward glances between the other members of the meeting. There was a slight delay and then Lisa withdrew a light blue sheaf of papers from the folder and handed it to the Director.

“My apologies Sir. I think you’ll find it’s all there.”

The man smiled and nodded. Lisa looked at Drew and he shivered inside. She had a look of triumph in her face but it was mixed with something else. Her face bore a look of satisfaction – pleasure almost. He sat quietly for the rest of the meeting. He didn’t get it. Why was someone so perfect outwardly, full of so much ill will? And why him? She could be curt and had high expectations with other people, but it was only he that received the kind of abuse that he experienced in the meeting. Drew returned to his desk feeling a little hollow. The job paid well, but money wasn’t everything. Yet, the working conditions were good and the bonuses generous. He just wished Lisa would get off his case.

It was the Wednesday and Lisa had asked Drew to stay late. He was meant to be taking his girlfriend out, but when Lisa asked he had learned not to argue. He had made his mind up to see out the month and hope things settled down. Lisa had emailed him a list of sales figures as long as his arm and he needed to get answers by seven thirty. Frankly it was impossible and his heart sank as he heard her footsteps approaching. He had observed that her skirt was rather shorter than normal, so that on occasion he had lost time, staring at her as she moved here and there.

“How are you going with those numbers Drew?”

“I… I’m struggling a little, I might have something by eight.”

Lisa furrowed her lovely brow.

“Sometimes Drew, I actually think you’re taking the piss!”

Drew’s heart began to beat faster as she stepped towards him. Without warning, she put one foot out and drove her heel into his instep.

“Ow! Nooo! Lisa, you’re going too far!”

Drew leaned back in his chair, his body involuntarily bracing itself for another attack as Lisa stepped closer. But her next move wasn’t violent. She merely stood over him, her legs parallel with his thighs and to Drew’s consternation, she began to lift her skirt. Drew was transfixed, and at the same time his cock began to grow and grow rapidly. He had never known a woman with such sexual power as she had. She was wearing skin-tone pantyhose with contrasting black suspenders. Her eyes were fixed on his, burning into him as she wriggled her hips until her concertinaed skirt revealed her white panties.

Drew gasped. Her panties followed every contour of her pudenda, from her smooth mound of Venus to the camel toe that had formed between her legs. Drew saw that her panties were a shade lighter there and he knew that she had made them wet.

Lisa’s next move was to grab his tie and she removed the knot deftly and then took hold of each end and used them to pull Drew towards her. Drew found himself looking up at her magnificent breasts as she spoke.

“Do you know why I treat you how I do?” she asked.

“I don't.”

“Because it makes me hot, it makes me horny Drew.”

Lisa licked her fingers and brushed the front of her panties, rubbing them against the front of her pussy. She looked down, and Drew knew she had noticed the swelling in his trousers.

“Take it out!|”

“Lisa, I’m dating. I’m flattered, but…”

“Take it out!!!”

The second time, she said it with some menace. She also began to unbutton her blouse. In spite of his misgivings, the sight of her skirt round her waist, her amazing legs and her blouse coming off was too much. His cock was so hard, it was beginning to hurt. Drew knew then, that there was no way out of this. She was the sexiest woman he knew... and some. Part of him wanted to jump up and run. He would send his notice by post. But another part was overwhelmed – by her. His nose was receiving the most glorious scent as she removed her blouse and his eyes beheld her breast cleavage with awe.

Drew unzipped his trousers and fumbled with his boxers. His cock had become pressed hard into the cotton and it took some time to extricate himself. Lisa licked her lips as she saw his seven and a half inches of thick cock. She looked at him searchingly, as she took his tie and pulled one end, drawing it, serpent-like through the neck of his shirt. She looked at his throbbing penis and as she did, she made a loop out of one end of the tie and lowered it, until she had lassoed his cock. Drew wanted to protest, but he was captivated by her and caught in the moment. Suddenly, Lisa yanked the tie, sending a sharp pain into Drew’s dick. She pulled the tie, and Drew had no choice but to stand up as she guided him to the end of the desk.

For a while Lisa played with him, using his cock like a puppet. Drew felt stupid, like some pathetic toy but his erection was as hard and pumping as he had ever known. She led him around the office her bum cheeks wiggling. Drew followed like some bizarre puppy, his cock leashed. Then she stopped at his desk. She pulled at the tie with a downward jerk making Drew grimace, as his cock was forced into an unnatural position.

“Get on your knees and it won’t hurt, will it!” said Lisa. There was a darkness in her voice, which made the hairs on Drew’s neck bristle. Drew did as she said and she stood over him, pulling her skirt as high as it would go and pulling his head forward, so his nose pressed into her soaking wet panties. Drew nuzzled against her sweet cunt lips, her panties translucent from her juices. His cock ached, a mixture of pain and pleasure. His intense erection and the abuse it had received merging into one.

Drew murmured incoherently, groaning as her sweet musky scent pervaded his senses and he just licked and sucked at her panties, tasting her. As if unsatisfied, Lisa took a handful of his hair and pulled, pushing his head back in the same move, bringing water to his eyes.

“Stand up Drew!”

She undid the loop on the tie and ran her fingers upwards along his shaft. In her heels she was the same height as Drew. She was so close to him now, he could feel her hot breath on his face. Her finger nails were drawing lines along the length of his cock. It only heightened his arousal.

“Undo my bra Drew,” she said calmly.

A shiver of panic ran through Drew’s body, as he looked down at her pink brassiere. He could already see the outline of her nipples through the lacy fabric.

“What are you waiting for Drew?”

Drew put his arms around her back and felt for the clips, which were the only thing between him and her heavenly boobs. As the last one was released, Lisa prodded Drew’s chest, sending him back towards his desk. Her bra fell away as she manhandled him into his chair and in the same move, Lisa held onto his shoulders and climbed onto him. She placed one hand around his neck, as she manouvered herself into position. Her breasts were swaying in front of Drew’s face, her beautifully pink nipples brushing his lips. Then there was a mutual gasp as his cock slowly impaled itself deeply into Lisa’s pussy. She was so hot and wet. Hotter than he could have imagined. Lisa’s bum began to rise and fall, at the same time she pressed her boobs into his face. Drew drank in the scent of her breasts, a combination of a natural milkiness and the delicate perfume of her body lotion.

Lisa ran her fingers up and down his neck, scraping her finger nails over his scalp as she fucked him. Drew’s cock was hard to bursting and yet he knew that to come too soon would be as heinous a sin as he could commit. She demanded perfection and that is what he would have to give her. The spring piston on his office swivel chair began to squeak as the thrusts of Lisa’s hips grew stronger. Drew felt like his cock was being consumed by Lisa’s pussy. It wasn’t just the amazing sensations in his loins that made the moment so intense. It was her. Her oceans of aureate blonde hair adorned his face as he suckled at her breasts. Her body had its own demanding aura, as she thrust and bucked on his cock. Her mews of pleasure were strangely cute and plaintive, not in keeping with her dominant nature. Drew lifted her a little, so he could drive his cock into her, timing his thrusts between hers. Her moans grew louder and her grip stronger, one hand moving onto his shoulder, her nails making deep impressions into his shirt.

“Yes Drew, at last you’re fulfilling your role…” she said, gasping, her eyes half closed, as she bit her lip.

Drew just gritted his teeth, his face pressed into her neck as she raised her body and ground her pussy into his cock.

Drew was in some other place, an out of body sensation surrounding him as the weight of Lisa's body bore down on him in a moment of energetic sex. His chair rolled back, hitting the window sill and then she pulled them round, holding the desk, but sending his mouse and keyboard flying as his cock pounded her pussy.

“Yeaaaaaargh! Yes Drew!!! There was a pause as Lisa’s body trembled and she ripped his shirt open and jerked her hips backwards and forwards, sending herself and him into a delirious pre-orgasm.


“Oh… Lisa!”



“Yes… Ooooooh… aaaaaaaaaaaah Drew!!!”



Drew took hold of her, his arms embracing her, as his hips lurched and he unloaded load after load of hot spunk into her pussy. Her hands cupped his face as he came and she pressed her breasts around his nose and mouth. Her breathing was deep as her body convulsed and she came on his cock in wave after wave of orgasm.

The light from the moon shone through the office window as they relaxed and Lisa twirled his hair around her fingers.

“What are we going to do with you?” she said.

Drew looked into her eyes as she kissed him. For some reason, he knew his time at Skintight Cosmetics wasn't going to be easy, but for all the abuse there would be the delightful rewards as the Mistress gives to her subordinate.

He wasn’t leaving Skintight. Not yet, at least.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Copyright © 2011-2018 Danielle Marsh. All Rights Reserved. This story may not be copied or reproduced, without the express written permission of the author.

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