Jenny Finds Herself

"Jenny is a insecure woman who finds herself when her boss asks her for a favour."

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“Jenny, get in here!”

It was not even eight in the morning and Mr. Kempel was already screaming at her. Jenny picked up her notepad and a pen and then made her way around the secretary station. The short walk didn’t take more than five seconds but when she walked into the big corner office Mark Kempel sighed and said, “you did take your sweet time. Sit down and take notes.”

“Sorry, Mr. Kempel.”

Instead of answering he indicated with his hand for her to sit. She took about two pages of notes for a memo he wanted written and then he ushered her out asking her to close the door after her.

Back at her desk Jenny sat down and opened a word document on her PC. Then she quickly typed out the memo and e-mailed it to the staff members that it concerned. She saved a copy in a file and ripped out the notes from her pad and saved them in a folder.

Two minutes later Mr. Kempel came out of his office and walked up to her desk. He was a tall man, in his late thirties. Is blonde hair was neatly cut and his horn-rimmed glasses were expensive. His tailored suit was imported from Italy and so were his shoes. The shirt came from a small shop in Singapore that specialised in hand sewn silk shirts. They went for around $500 a pop, according to the bills Jenny received.

“I’m going out, and I don’t know when I will be back,” he said. Without waiting for an answer he turned around and walked with long steps to the double oak doors and left the office.

Jenny sat in the silence and breathed out. She loved having the place for herself. Below her on the other six floors of the building, a staff of around three hundred people worked to make Mr. Kempel more money. She was the only other person working on the seventh floor with him, and she was proud of it.

Jenny Walker was twenty-five years old and a graduate from one of the better business schools in the country. When she graduated, the competition was hard, even for a brilliant student like her and the only job she found was as an assistant which was a nicer word for a secretary to Mr. Kempel. The pay was good, but the hours not so. She would be at the office before seven in the morning and seldom leave before nine at night. Luckily she only lived six blocks away so it didn’t take her more than half an hour to walk home.

She didn’t own a car and didn’t like using public transport. The city where she lived and worked was relatively safe so she walked, to work, to the shop, to the cinema and always alone. She had no friends, only acquaintances from university, but they all had kids and husbands and didn’t invite her to their parties.

She had no boyfriend only Joey, and he was more of a fuck buddy than anything else. They never went out together, or eat together at home. The only thing they did was to have sex, and it was shitty sex at that.

Jenny did know what good sex was, thanks to professor Lambert. He had fucked her so well, that by the time it was graduation day she wanted to give him an A instead of him her. That he was twenty years older than her didn’t mean a thing. He made her come, and that was it. In return, she had helped him grade his undergraduate’s exams and papers. It was a win-win situation.

Jenny got up and walked over to the pantry where she made herself a cup of black coffee and took a cookie out of a tin box. There was another tin box in the cupboard but that belonged to Mr. Kempel and she was not allowed to eat his cookies, they came directly from Austria by Fed Ex.

Taking her coffee with her she went back to her desk and opened the calendar. It was Friday and on Sunday, she had typed in Joey. He was to come around her place at seven for their usual twice a week fuck. She didn’t look forward to it at all and even contemplated cancelling it. Joey wanted her to do all kind of things she didn’t really like, anal sex being one of them.

He also wanted her to take his cum in her mouth, which wasn’t such a big deal, but still, not something she looked forward to. The problem was if she cancelled he might get pissed off and end the entire relationship if you could call it that. Jenny was lonely enough; she didn’t need to be any more lonely.

Her problem was that she was extremely insecure. Her father had made her that way. She had suffered from Dyslexia as a kid and her father had reminded her every day that she would amount to nothing. She would end up with a shitty job, in a shitty town with a shitty husband and little shitty kids.

He had only been partly wrong. Jenny had worked hard and earned a scholarship to University, and with special help from almost all her teachers she had graduated with good grades. She never went home after graduation, just jumped on the first bus that stopped on the street with one suitcase and her diploma.

But the stigma didn’t go away. She felt like a loser, a nobody, not even her co-workers below who respected her for having to deal with Mr. Kempel made her feel any better.

She was a pretty girl, or at least that’s what people had told her. She wasn’t very tall but had the right proportions, dark blonde hair that was naturally wavy and dark blue eyes. Her skin was light brown from her Mexican mother, but the rest was from her blonde father.

She began working on a few reports that had to be done by the next day and around seven she decided it was time to end the day. The boss wasn’t in and she needed to stop by the shop to buy some food.

She was just about to turn off her computer when Mr. Kempel came rushing in through the double doors.

“Don’t make plans for Sunday, we are leaving town.”

“What?”

“Don’t argue, be ready outside your place at six in the morning, I will pick you up in the limousine, and then we go to the airport.”

“Where are we going?”

He waved his hand, like if he was dismissing her, then turned around and walked into his office and closed the door. Two minutes later the intercom buzzed. “Jenny, you can take the rest of the day off.”

Thanks, asshole, she thought and left.

From home, she called Joey and cancelled their date. He sounded angry and hung up the phone before she had a chance to explain it wasn’t her fault.

The rest of the evening she spent doing laundry and cleaning her apartment. She ended it with a glass of white wine and a book. There was only one thing that Jenny enjoyed spending money on and that was good wine. She had made the closet in the guest bedroom into a wine cellar and she kept the temperature perfect for the red wines and had the white’s and rose’s in a wine fridge.

She had over a hundred bottles in her collections and she would spend hours on the internet at night looking for bargains. Some of her bottles cost several hundred dollars and she only drank them on special occasions, like her birthday, Christmas and her mother’s birthday.

While she read the book her mind drifted back to Mr. Kempel and why it was so important that she came along. He never took her on his trips, preferring to use the secretarial services at the hotels he stayed at. She would then have to clean up the mess the person had made and make sure it was exactly the way he liked it. Sighing she got up, turned off the lights and left the empty wine glass in the sink. The bed was cool and when she closed her eyes she drifted off quickly.

On Saturday, she went shopping. She bought a new skirt and a couple of tops. Mr. Kempel was very strict with her dress code. She didn’t have to wear a uniform per se, but she had to wear skirts with no patterns. The colour should be subdued and the skirt should end below her knees. On top, she could wear anything that didn’t have a pattern and didn’t show off cleavage or her bare arms. Her hair had to be neat and never hang on her shoulders. Her makeup had to be subdued and no bright colours were allowed.

One day she had used a new lipstick and when Mr. Kempel had seen her he had told her she looked like a slut and to change it immediately. She had felt hurt and had cried in the bathroom while wiping it off her lips. She never wore it again and had actually thrown it away as soon as she came home. Joey didn’t care about how she looked, as long as she was naked.

Back at home, she packed her bag for the next day and in the evening, she went to the movies. She liked going alone. She could choose whatever movie she liked, eat what she liked and drink too much soda. The movie made her cry but she enjoyed it and when she walked home that night she thought about what had happened to the couple in the movie and realized that she had it pretty good.

On Sunday morning, she was standing outside her building when a black limousine drove up and came to a silent stop in front of her. The driver, in an immaculate uniform which included a hat, came around and opened the backseat door for her she thanked him but he only nodded.

“Good morning Mr. Kemple,” she said when she had sat down opposite her boss.

She could see the driver put her suitcase in the trunk and then walk to the driver’s side.

“Good morning, Jenny.”

That was all he said until they arrived at the airport. Instead of stopping at the departure area the car drove around to where the private jets stood and parked in front of a Lear. The stairs were down and the captain and co-pilot waited at the bottom. When the driver opened the door both of them shook Mr. Kempel’s hand and gave her a courteous nod before following them up.

The interior was all leather and dark wood. Mr. Kempel poured himself a whiskey but didn’t offer one to Jenny, which wasn’t strange. He sat down in one of the oversized chairs and looked at her for a long time before saying, “we are going to Las Vegas.”

“Oh,” was all Jenny said. She had no idea that her boss liked gambling.

“I’m buying a casino and it’s a very hush-hush deal. That’s why I can’t use local help and had to bring you.”

When he said it sounded like if she was a burden on him and it made her wonder why he had bothered. He could have taken a temp from one of the many companies that hired them out in the city.

“I need someone I can trust, and who I know can keep their mouth shut.”

That explained it, thought Jenny. After that, he didn’t say a word during the four-hour flight. The co-pilot came out from the cockpit and served them a delicious breakfast and after that Jenny read a magazine she had brought with her. Mr. Kempel slept for an hour and woke up when the pilot told them they were about to begin their final descent .

Another limousine picked them up and drove them to one of the new luxurious hotels that had been built during the last year. Jenny got her own suit which was bigger than her apartment. Mr. Kempel stayed two doors down in an even bigger one. By the time she had washed her face and unpacked it was ten in the morning. She was about to pick up the phone to call her boss when it rang.

“Jenny, meet me in the lobby in ten minutes and bring your laptop.”

She checked herself in the mirror and apart from looking a bit tired she decided she was OK.

She had to wait a little while before Mr. Kempel stepped out of the elevator and walked up to her. Instead of speaking, he took her arm and almost dragged her along a corridor that had a sign saying it was the way to a conference room. At the end of the corridor was a door, and when he opened it and ushered her inside he found herself in a small room with an oval desk and six chairs.

Four of them were taken with three men and one woman, all dressed very expensively and looking very serious. On the table stood a few bottle of water and soda and six glasses.

“This is my assistant Jenny. Her last name is not important; all you need to know is that I trust her.”

The other four nodded and Jenny and Mr. Kempel sat down.

It took them five hours to hammer out the deal. For a while, it looked like it would fall apart, but the woman changed her opinion about certain issues and in the end everyone got what they wanted. Jenny was quiet as a mouse, just typing everything that was said and agreed upon. When she was done she took a portable printer from her bag and printed out five copies of the contract. The men and the woman read it and asked for a few changes.

After they had all signed it, they left one by one. Jenny and Mr. Kempel was last to leave. When they walked along the corridor he suddenly stopped and turned around.

“Jenny, I really appreciate you being here today. Even though I pay your salary, and pretty much run your life, having you here today made this happen. If you would excuse me, I have some personal business to take care off during the rest of the day. You are free to go to the pool, or use any other of the hotels services. Just sign for it.”

“Thank you, Mr. Kempel.

“Good, then I’ll see you at seven tomorrow morning.”

She watched him walk away from her and smiled. Holy shit, she thought. That was the nicest thing he had ever done or said to her since she began working for him.

Jenny floated in the pool while the dessert sun burned her skin. She had bought a bikini in a shop in the lobby and then gone down to the pool area.

While she floated on the water she wondered what kind of personal business her boss was up too. He had no family, no wife, no kids, and no parents. Maybe a cousin? Or and uncle or aunt, but she didn’t think so.

She began swimming back to the steps and got out. She was hungry and after drying herself off she collected her towel and purse and made her way to the poolside restaurant. A handsome young man greeted her and sat her down at a table in the shade where she ordered a hamburger from the menu and a glass of ice water with lemon. The waiter was also younger than her and very hot, she thought. Looking around her she noticed that most of the men were good looking. She sighed and wondered when she would ever find enough courage to ask someone like them out.

After eating she made her way across the lobby towards the elevators. It was close to four in the afternoon and she was leaning against the wall when she spotted her boss coming in from outside. What caught her attention was the tall brunette he had his arm around.

Jenny knew what beauty was, and this woman was something else, tall, and ravishing with the right amount of makeup, high heels, short skirt, and a tight top with bouncy boobs. Her hair was long and raven black.

Jenny ducked around the corner to avoid being seen and then spied on Mr. Kempel as he walked passed her hiding place, aiming for the a la carte restaurant.

She guessed the woman to be her own age or a year or so younger. She heard her speak as they passed her and her voice was educated and a little horse. It sounded sexy in a way.

When they had disappeared into the restaurant Jenny went up to her room and took a shower to get the chlorine off her skin. Then she dressed in a fluffy bathrobe that the hotel provided and went to open the mini-bar, she needed a drink, or two.

Sitting in the suits living room with her feet up on the glass coffee table and a double vodka-orange juice in her hand Jenny contemplated what she had seen.

The first word that came to her mind was a prostitute . Now, Jenny understood men’s needs and didn’t judge her boss. If he wanted to pay to play, it was his business and his money. What bothered her was the way the woman had been dressed. It was the exact opposite of what she had thought Mr. Kempel liked.

She made another drink and turned on the TV. She decided not to order dinner since she was still full after the huge hamburger she had eaten. Instead, she nibbled on some peanuts provided by the hotel and sipped on her drink while watching TV.

At ten she decided it was time for bed. She had had three cocktails and her head was spinning a little when she stood up. After brushing her teeth she got into bed and turned off the light.

She drifted off but didn’t make it all the way to sleep because the bedside phone rang.

“Mm, yes?” she mumbled.

“Jenny, I need your help, come to my room.”

It was Mr. Kempel, and he didn’t sound sober. Jenny turned on the light and swung her legs over the bed. She couldn’t be bothered getting dressed. If he was drunk and had puked she would have to take care of that in her bathrobe.

When she knocked on his door he opened immediately, like if he had been waiting by the door. She grabbed her arm and pulled her inside and then kicked the door closed.

“What is it, Mr. Kempel?” she said.

“Come, and please, take a seat. There is a favour I need to ask you for.”

“OK,” she said and followed him into the much larger living room.

There were two glasses on the table and she noticed red lipstick on one of them. In the air hung an exotic aroma that must have been the hooker’s perfume. Jenny looked around before she sat down on the sofa where her boss indicated for her to sit. She saw no signs of the other woman.

Mr. Kemple cleared his throat. “Jenny, what I am about to ask you, is very personal to me, and I understand completely of you don’t want to do it. I want you to know that it will not reflect on your standing with me as my employee. Is that clear?”

“Yes, but can I ask a question before you continue?” she said.

“If you must, please go ahead.”

“I saw you with a woman, earlier, in the lobby. Who was that?”

Again he cleared his throat and picked up the glass without lipstick. After finishing the liquid inside, he said, “that was Anastacia.”

“OK..?”

“She was to perform certain services for me, but she didn’t, and that’s why you are here.”

Jenny felt her blood pressure rise. What did he think she was, a whore, that he could just fuck? Her hands began to shake and she grabbed on to the arm rest.

“Are you OK,” he said.

“No, I’m not. If you think you can treat me like a hooker you are dead wrong, Mr.Kempel. I’ll fucking quit before I let you fuck me.”

To her surprise, he leaned back and began to laugh. It was a deep, beautiful sound, and she became confused. Had she missed something?

“My dear Jenny, this is about fucking, yes, but I want you to fuck me, not the other way around.”

Now she was even more confused. “I don’t get it.”

Instead of answering he stood and walked into the master bedroom, and when he came out a few seconds later he was carrying something in his hand that he put on the table between them and then sat down.

“Have you seen one of those before?” he said and pointed.

“No.”

“It’s a strap-on cock. Lesbians use it sometime.”

“Oh, OK.”

“I want you to put it on and fuck me.”

“Why on God’s earth would you want me to do that?

“It’s hard to explain, but it has to do with trust, and letting go of whom you are, and what people think you are.”

Jenny was completely lost. Sure, she knew what a strap on was used for, and that some guys liked to have a finger up their asses when their woman jerked them off or gave them a blowjob. But having a woman fuck them, with what looked to be an eight-inch dildo, was something else.

Her thoughts were cut off when Mr. Kemple said, “so? Will you do it?”

“What happened to Anastacia?”

“She was a spy, sent to me by my competitor to get pictures of me when we did the thing. I overheard her on the phone when she was in the bathroom, and simply kicked her out.”

Jenny had an interest in sex, even though she hadn’t had many partners. Her time with Professor Lambert had been very educating from a sexual standpoint and she had learned a lot. The idea of fucking her boss in the ass was something she would gladly do.

“OK, I’ll do it, but on one condition.”

“What?”

“I can call you Mark, and for this night, I am not your secretary, I am the woman who will fuck you up the ass.”

He chuckled, and then said, “sure, Jenny. That is fine.”

Mark picked up the harness from the table and signalled for her to follow him to the bedroom. While he walked ahead of her he began to undress so by the time they entered he was only in his white silk boxers. The rest of his clothes were on the floor along the way.

“I assume you have never done this before?” he said turning to Jenny.

She shook her head.

“That’s OK. I will tell you what to do. It is important that you understand that I have done this before, so don’t worry about if you are hurting me or not. The dildo is just right for me.”

The way he talked was like if he was giving her directions on how to turn on a washing machine. No emotions, just directions.

“What do I do now?” she said.

He smiled at her and indicated with a finger, “take your clothes off.”

Jenny was a bit shy about her body. She didn’t like it, and when she was with Joey she insisted on having the lights turned off before she took off her clothes.

When she reached for the light switch Mark put his hand on hers.

“No, leave it on.”

“But…”

“I like it on, and you don’t have to be shy around me.”

Jenny opened her bathrobe and let it fall to the floor. The room was a bit cold because of the AC so she shivered a little.

“Wow, just look at you. I had no idea you had such a great body,” said Mark and walked around her.

“Well, you always have me wear those boring clothes.”

“And you will continue too. I am not sharing this knowledge with anyone.”

When he had completed the circle he put the harness on the bed and then pulled down his boxers. Jenny instinctively looked away.

“C’mon, look at me,” he said.

She turned back and smiled inside. Apart from having a great body, his cock looked very tasty. Quite long, with a big head that peaked out from his foreskin. He was semi-erect and she could see the outlines of the veins snaking around his thick shaft.

“Like?” He said while smiling and looking down at his dick.

“Mm, it’s very beautiful.”
He laughed. “That’s the first time someone had used that word to describe my cock but I like it. C’mon, get on the bed with me and we’ll get this harness fitted on you.”

The sheets were cool to her skin and the bed was huge. It must be bigger than a king size, she thought as she climbed on to it. She moved so she was sitting cross-legged in front of Mark.

He looked down at her cunt and smiled. “It’s cute.”

Jenny blushed. “What do you mean, cute?”

“It looks like a teen pussy. You know, the lips are not big enough to protrude from the slit.”

“Oh, I never thought about that,” she said and looked down at herself.

“Stand up,” he said and did the same.

He proceeded to put the harness on her and his hands were warm when he touched her. When he had tightened it and had made sure it wouldn’t come off, he stood back.

“Wow, I love the way you look.”

Jenny turned on the bed, carefully not to lose her balance and checked herself in the large mirror hanging on the wall. The skin coloured dildo stuck straight out and when she made a few thrusts it bounced up and down and she giggled.

“It looks funny,” she said.

“It looks hot.”

Mark knelt on the bed and reached over to the bedside table which he opened and took out a tube of lubricant. After pouring a large amount in his hand he turned towards Jenny and began to slowly smear it on the dildo.

Watching her boss kneeling in front of her while lubing up a sex toy that she soon would thrust into his ass made her feel something that Jenny had never felt before. At first she wasn’t sure what it was, but then it dawned on her. It was power. She would be in charge, she would take control, and she would do the fucking. Not the other way around, which it had been since the first time she had a cock in her.

Mark looked up at her and said, “I can feel your pussy warming up. Are you wet?”

“Yeah, I think so,” she said in a husky voice.

“Good, I want you to enjoy this as much as I.”

With those words he took the dildo in his hand and then licked it from the base to the tip. When he reached it he made eye contact with her while he took it deep into his mouth.

Jenny swallowed and just stared at her boss while he sucked the cock attached to her. She had never seen anything so hot in her life.

“Doesn’t it taste funny?” she asked.

Mark slowly shook his head and mumbled. “The lube tastes like strawberries.”

He kept on sucking and licking the dildo while she watched him. And when he was done he turned and got on his knees and elbows. He was maybe a foot from her and she wasn’t exactly sure what he wanted.

“What do I do?”

“Take my balls in your hand and slowly massage them.”

She slipped her right hand between his legs and he adjusted himself so she could reach them easier. They were hot and warm. His cock was limp, which was a surprise to her.

It hung straight down and when she reached for it he said, “leave it alone for now. Just play with my nuts.”

She did what he asked and after a minute or so she noticed how his shaft grew thicker and his head popped out from behind the foreskin. Since he didn’t say anything she continued massaging him.

“That feels so good,” he moaned and moved a little. He reached for two pillows which he put on top of each other and then lay down his head.

Suddenly Jenny noticed a drop on his cockhead and figured it was pre-cum oozing out. With her left hand she dipped her finger in it and brought it to her mouth.

“Mm, you taste lovely,” she purred.

“Glad you like it. You can begin to fuck me now. All you have to do is put the tip of the dildo against my anus and maintain the pressure.”

She did what he asked and saw how the tip slid in an inch or so. Mark moaned a little and then he pushed back against her. Another inch slid in, and then the entire head of the dildo was inside him.

“Mm, I love it,” he groaned and pushed back harder.

Jenny couldn’t believe her eyes. His ass opened up and she slid all the way inside him.

“Wow, that was amazing,” she whispered.

“Now grab my hips and slowly fuck me, not too hard and not to slow.”

Jenny did what he had asked and within a minute she began to moan.

“Take that you bitch, yeah, take it.”

To her surprise Mark went along with it.

“Yes, I am your bitch, please fuck my ass,” he moaned.

“Take it, take it, take it,” she almost shouted as she thrust in and out of him.

“I love your cock, give it to me.”

Jenny’s pussy was so wet by now that she could feel a drop or was it two running down the inside of her thigh. The emotions she was going through went from anger, to sadness to euphoria. Without thinking about it, she began to fuck him harder and harder, with deeper thrusts. All the anger that had built up inside her during the years from being used by her lovers came out through the dildo attached to her.

“God, woman, what is it with all the anger?” moaned Mark, and looked at her over his shoulder.

“Shut the fuck up, and take it you bitch.”

“I love it, no complaints.”

Instead of answering him she pulled out and pushed him onto his side and then moved his legs so they were in a missionary position.

“I want to see your eyes when I fuck you,” she hissed between her teeth.

Mark didn’t answer. Instead he put his legs up on her shoulders and she guided the dildo into his ass.

Mark’s cock was rock hard by now, and when Jenny grabbed it while she fucked him he moaned and closed his eyes.

She found a rhythm and while thrusting in and out of him she also jerked him off. He must have been close to coming, because it didn’t take long before he lifted his back off the bid and his legs began to tremble.

“Oh yes, oh yes, here it comes,” he said, his voice changing pitch

Jenny watched the large globs of cum squirting out of his shaft. One, two, three, four, five of them landed on her and him before she let go of his cock and pulled out of him.

She fell forward next to him, and just lay there catching her breath. Mark was breathing heavily beside her and he was the first to get up.

She watched him walk to the bathroom and a minute later she heard the shower come on.

Jenny flipped over onto her back and lay there staring at the ceiling. Then she looked down at the harness and the dildo attached to it.

“That was fun,” she said to herself.

When Mark came out he walked over to the bed and crawled up between her legs.

“You didn’t think I would leave you hanging, did you?”

She giggled. “I was hoping you wouldn’t.”

Instead of answering, he spread her legs and ran his tongue along her slit.

Jenny closed her eyes and let her boss lick her to first one orgasm and then another, right after each other.

When he pulled away he said, “you taste so good.”

“Like strawberries?” she managed to say between deep breaths.

“No, better. Like a horny woman.”

They were silent for a while and then Jenny asked, “what happens tomorrow?”

“Nothing. Everything goes back to normal. You are my secretary, and I am your asshole for a boss.”

“Oh,” she sounded a bit disappointed.

He ran a warm finger along her jaw line. “There is one difference, though.”

She kissed his fingertips, and then took it into her mouth and mumbled, “what?”

“From now on, you are coming over to my place on Saturdays at seven in the evening. I’ll cook dinner and you will fuck me.”

She let go of his fingers and leaned on her elbow, looking into his eyes.

“Why? Why do you like this?”

“Because I am who I am. I’m always in charge, I am always the boss, and no one ever tells me what to do. This is my way of finding relief from the stress and pressure that builds up. I get to become the submissive, the one being told what to do. I love it.”

“Oh, I see.”

He kissed her on the cheek. “It’s time for you to go back to your room.”

When Jenny was in her bed alone, she closed her eyes and thought about what had happened. It was something new, something exciting and for the first time in her sexual life, she looked forward to having sex with a man. Well, she was looking forward to fucking a man.

Published 9 years ago

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