Sarah's Made a Huge Mistake

After two years of looking for employment, Sarah had entered a state of despair. Her student loans continued to rack up interest as her parents worked to pay them off temporarily. She struggled to find some form of steady employment while drifting from one part time job to the other. Men always had a go at her, grabbing her full bottom or touching her supple thighs as she did her menial jobs, leading Sarah to quit in frustration a few times. She was tired of her menial work when she had studied so hard for more.

When Sarah's dad told her that his friend had a position at his firm and she had an interview, she was absolutely relieved. It was a small investment firm, but anything was better than that gaping hole on her professional resume. The interview went smoothly, and she was hired within weeks. The boss, Henry was an ordinary looking man, with greying hair and a slight fullness around the midriff, with a kind face.

The first few weeks were quite the struggle, where Sarah had to exercise her brain and re-learn the things she had forgotten over the years. Henry was the nicest boss she ever had. He was particularly tolerant of her mistakes and always smiled gently, his eyes twinkling. Her colleagues were helpful, guiding her work and assignments.

A couple of months in and things were going smoothly, and Sarah believed that things were good. Until today, when she had mistakenly approved a transaction that would cost the firm a good $100,000. She spent the rest of the day in great anxiety, exploring the many ways out in her mind but never coming to a solution. Eventually, everyone but Henry had left the office, and she raised her wearisome body off her chair, walking into Henry's office with the worst case scenario in her mind - being out of a job again and having to rely on her poor parents.

"I'm going to have to let you go honey," Henry sighed, taking off his glasses and giving them a wipe.

It disappointed him that after a couple of months of seeing that fine, tight ass sway around the office that he would have to let her go for her stupid mistake. He should have expected that pretty girls like her really didn't have much going on in their brains. She probably slept with her professors and tutors to get her degree.

Sarah's heart sank, and a tear began to leak out of her eye. "Please, I would do anything to keep this job. Tell me how I could make this right, Henry. Please..." Sarah mumbled. She felt the sobs coming in. Sarah couldn't lose her job, not again.

Henry was a shark. He was a kind looking, sweet and deceiving shark, and he seized the opportunity to say "Anything sweetie? Anything?" He felt himself hardening as his mind raced at the possibilities.

As Sarah muttered an affirmative without thinking, Henry stood up and walked to her, tenderly wiping her tears away. He placed his hands on her shoulders and told Sarah that she was responsible for the loss of a 100k and that no other firm would hire someone who made such a big mistake. Sarah's mind raced towards the darkest thoughts, and said she would do anything to make it right.

And as Henry nodded, he pushed on her shoulders downwards, causing Sarah to stagger and kneel suddenly on the ground. Her eyes confronted Henry's large bulge and she couldn't process what was happening in front of her eyes as Henry unbuckled his trousers and pulled out his erection, pointing it at her sweet, sweet lips. Sarah's mouth fell open in shock as she comprehended what Henry wanted from her. His cock was so large and engorged, bigger than any ex and it looked like it belonged on a porn star.

Seeing that Sarah was stunned and unmoving, Henry told her she had only one way to keep the job, and pulled her head towards his dick. Stunned, Sarah did the only thing that she could think of, and licked the tip of his dick ever so slightly. If a blow job meant she could keep her job, she would do it.

"Good Girl", Henry nodded, pushing his engorged cock into her mouth, his hand fisted in her hair. Sarah mewled as the she tried to slurp on the cock - she was never the best at blowjobs, after all, and she could hardly fit his cock in her mouth. He started aggressively pumping his cock into her mouth as she choked and coughed every time it hit the back of her throat, pulling herself back to take multiple breaths.

"You can't even take it halfway in" Henry scolded with disdain. He took out his phone and snapped a few pictures of Sarah trying her best to suck and please him. The sounds of the slurping filled his office as Henry continued to attack Sarah's mouth with his large, hard cock, trying to force it down her throat, but everytime, Sarah would twist away and it angered him. She didn't even try her best here! That merited punishment and training, in the future. After a few minutes of plunging his meat into her, he spilled his hot jizz over her mouth and porcelain skin in semi-satisfaction.

Sarah knelt, dazed and confused, with sticky globs of cum in her mouth and on her face. She moved towards a box of tissues and began to clean herself up, as Henry walked back to his chair and sighed.

"Henry-"

"Yes, Sarah?"

"D-do do I still have my job?"

"Yes, for now, honey"

Sarah cringed. That word honey, once so simple from a seemingly sweet man, seemed so laced with menace now. She was so disgusted at herself for giving in to this man, pleasuring him for the sake of keeping her job. It was almost as if she had whored herself out, and she had done it willingly.

"Thank you", Sarah whispered, but as she turned to leave, she was stopped.

"Not so fast. That sad blow job, I could get from a cheap hooker on the street for $20. That's $20 out of $100k. We are going to have to do much, much better than that. You know what? Give me a few days and I'll get back to you. Go home now. We still have to fix your mistake tomorrow."

Henry watched as her sweet face filled with even more bewilderment and her hazel eyes expressed much doubt. Sarah walked out of Henry's office, not knowing what the future held but feeling very, very uncertain.

The next few days went by in a flurry as Henry dealt with an angry client with Sarah backing him up on documentation and more work. It was as if nothing weird had happened. Her colleagues were supportive, reassuring her that everyone makes mistakes. Sarah dearly hoped she could put everything behind her.

It was Friday night when she got called into Henry's office and told to stay after work that day. Henry was a divorced man, and he had plenty of time to think of diabolical plans at home. He had written an entire document that was baffling to Sarah, with sexual acts and their monetary values beside them. He had done a lot of research and was completely satisfied with himself. He had written a detailed menu with specific sexual acts that had a simple monetary value, as well as hourly alternatives, such as roleplay, or bondage, for example.

"Scoot over here and lets get this worked out", and Henry opened his Excel sheet for Sarah to see.

As he presented the document to Sarah, she gasped "No way! I don't even know what most of these are! WTF is wrong with you! What do you want with me!? If this is what it's going to be like I think I rather quit!"

A sinister grin spread across Henry's face as he took out his phone and showed Sarah the pictures he had taken earlier that week. He told Sarah patiently that she could choose to quit and have her pictures of her sucking dick spread online, or she could work off her debt slowly and steadily.

Sarah shrunk in her chair. She didnt even notice Henry taking pictures that night, overwhelmed as she was. She was an immensely private person that never let her ex-lovers take intimate pictures of her - the moment these pictures got out she would be completely embarrassed. She would be gone. The realisation dawned on her that Henry had her completely cornered, and she nodded.

With tears in her eyes, she tried to study the content on the monitor in front of her. She didn't even understand what half of the things were. Vaginal, anal - of course she got that, but being vanilla as she was, the rest were completely foreign. Her ex-boyfriend was perfectly satisfied with a mediocre sex life, and she never did explore much.

"This is what we will call our Menu, Sarah. Every item on the menu has a corresponding value to it, and every time you deliver, we deduct it from your debt. Any questions?"

"I don't even know what most of these are! And I've never even done anal, so I don't even know how we will be doing these! It's completely unfair..." Sarah sputtered indignantly.

Henry could not have been more delighted. He was dealing with a complete innocent, for him to use and manipulate as he pleased. He knew her parents were conservative, but they clearly sheltered their daughter well, too well.

"Well, Sarah, lets do this. You are an anal virgin! So lets up the price for losing your virginity. Lets change that to $1000 for the first time. You can go home and research the rest, but just know that I have been exceptionally generous with everything so far."

As Sarah numbly nodded and took in the information, her mind wandered. Some of the amounts seemed to be on an hourly basis, and at $1,000-$2,000 per hour, she had that fleeting thought that she could get out of this with time.

"Do you have a boyfriend?"

"No"

"Are you still staying with your parents?"

"No"

Henry nodded. No boyfriend was a good thing. He couldn't comprehend why, though. Sarah had the perfect, curvy figure and a sweet, innocent face. Other than that tight, round butt he was crazy about, she had a very ample bosom, perhaps a C cup.

"I'll pick you up next Saturday morning. Let's start knocking off some of that debt then, alright? A whole day should give you a good headstart, eh? Work - work will be as normal. Lets be professional here. I'll give you a heads up if I want anything extra on the side. "

Sarah nodded slowly in agreement. She was trapped, and she knew it. She couldn't figure out a solution yet, but damn if she was going to accept everything. In time, in time she would find a way out of this damned snare.

Henry stood up then, and smiled at her.

"Alright, come on, lets check you out! Fuck... I've wanted this hot body of yours ever since you walked in for that interview" He muttered as he groped her ass and her breasts relentlessly through her thin blouse and skirt.

"Come on, come on, take off your clothes!" He barked at Sarah as he started fiddling with the buttons on her blouse. He really wanted to get to her breasts, practically tearing off her blouse until he exposed that porcelain chest of hers.

"Skirt, Sarah, take it off, I need a good look at you, you know. Don't be shy, we've already agreed on this, haven't we?"

As Sarah fumbled with her skirt and removed it, Henry took one good look at her and grinned. She was smoking. The clothes she chose to wear to work were always professional, and boring as heck. It didn't hug her figure at all. What a waste!

"From now on, I want you to wear better clothes. Tighter clothes. Shorter skirts. I want to see more of your curves. Don't ever wear panties or bras into work again. We want to work off that debt quickly, yes? And that means easier access, for gods sake!"

Henry pulled her soft, supple mounds out of her bra and caressed them, playing with her plump nipples, taking off her bra and releasing those beautiful breasts. He licked them and fondled them for a good few moments, before turning his attention elsewhere. Sarah had already removed her skirt, but left her panties on, so Henry deliberately peeled them off and ran his fingers down her shaved sex, her clit, before forcing two fingers into her dry slit. Sarah yelped at the surprise invasion and jumped away from Henry, which led him to give her a tight slap on her butt cheek. He pulled her towards him again and continued fingering her clit and attacking her pussy aggressively, pumping his fingers in and out.

Sarah had never been treated so aggressively before, but as her tears ran down her cheek she felt a little warmth in her sex and let out a small gasp. Henry grinned.

"Let's get you off, girl. I want to see you cum. Bend over and grab your ankles", Henry directed, and Sarah bent over, grabbing her ankles and exposing her sex towards Henry.

He licked her and sucked her clit all while fingering her, and felt her juices starting to leak out of her pussy.

"Mmmm, what a sweet, taste you have!" Henry said as he tongued her deeply.

Reluctantly, Sarah had started to moan and gasp as she was increasingly turned on by the sensations. Her position with her head down caused blood to rush to her brain and she was in a haze of pleasure. Henry had taken out a small butt plug and inserted it into Sarah's pussy grinding it around and pumping it in and out. This pushed Sarah over the edge and she came, shuddering and gasping. With that, Henry withdrew the plug which was coated in glistening juices. Without warning, Henry forced the butt plug into Sarah's ass and she shrieked at the unwelcome infringement.

"Stand up, Sarah" and he smacked her butt as she did so.

"You should keep that plug in your butt as much as possible this week. I don't want to be tearing you apart your first time" Henry sniggered."Let's head off, I'll close up."

Sarah sniffed and grabbed at her clothes. As she started putting on her bra, Henry shook his head. She had to get dressed with no underwear under his watchful eyes and leering grin. She couldn't wait to get to a toilet to remove the foreign object in her anus, but Henry walked her out to his car and drove her home. Every little bump made Sarah even more aware that she had something up her ass. The car ride was silent and awkward, but as she reached home Henry pulled out his rock hard dick and she had to suck him off again.

"See you Monday, Sarah. Come in earlier so we can catch up, okay?" Henry said as Sarah got out of the car, her mouth stained with cum.

As soon as she got home, she pulled out the unwanted butt plug and showered in hot water, scrubbing at herself while crying heaving sobs. It was going to be a hard week for her next week.