Office Blackmail (Closed for Aluris)

[Rocket1010]

Jack arrived early to his office and sat in his large oversized leather chair staring out the 35th floor window to the city. He always tried to arrive early, enjoying the peace and solitude of the office when none of his 250 employees were in the office.

Jack came up through the ranks of the overseas trading company and when the company CEO suddenly died of a massive heart attack, he successfully wrestled the reins from other inside competitors. Within a few short years he grew the company one-hundred fold and gained a firm grip on the control of the company. When they expanded Jack changed the name of the company to reflect his own name on the letterhead.

Turning from the other skyscrapers in the downtown area, he looked at his desk calendar, seeing that he had his last round of interviews for an open executive secretary position. There were some women in the company that thought they should have a shot at replacing Jeanette but he knew they would not fit the bill for what he was looking for.

His thoughts turned to Jeanette, his former executive secretary, who reluctantly left when her husband was transferred across country. He tried his best to convince her to stay but her husband was adamant about taking the new job and there was not much she could do but follow her husband. Jack continued to try and convince her to stay but to no avail and now he sat remembering their last late night together.

Jeanette had worn the sexiest outfit on her last day. They spent the rest of the afternoon behind closed doors giving Jeanette a wild sendoff. The office staff thought they were going over last minute details of all the things she was doing. What they did not know was that Jeanette was submitting to Jack's final demands for the last time.

A tingle ran through his balls as he recalled giving her a good spanking for leaving him and the sound of her constant moaning with each swat was still ringing in his ears. He made sure she was thoroughly subjected to his desires before he let her go early in the evening. He felt his cock thicken at the thought of her crawling across the floor, to his waiting cock as he sat in the large leather chair. The memory of her sucking his shaft until he came hard and strong in her mouth, made his cock jerk. Jack sighed thinking of that final day filled with sexual pleasures for each of them. As a last goodbye gesture, he fucked her against the glass window overlooking the city as Jeanette cried out so loud he thought the whole building heard her.

Putting the memories of Jeanette aside, he turned to his desk and began working, soon losing track of time. When the knock on the door came, he looked at his watch to see that his first interview of the day should be ready.

"Mr. Connors your 9:00 am interview is in the conference room."

"Thank you Ms. Jennings. I will be right there."

Jack opened the file and looked at the resume of Cassie Mays, the young woman he was about to interview. Looking at her resume, he wondered how she made it past the initial screening. 24 years old with a major in Modern History and never held a full time job. He began to think this interview would be a waste of his time as he scanned the rest of her resume. While reading the rest of her resume, he thought of the some of the other candidates for the executive secretary position. They were qualified to do the work but each one seemed to be lacking some of the other qualities he was looking for in a personal assistant. There were things in the resume and application that he could not ask because of laws restricting what he could and could not ask. He hoped during the interview process that he would be able to determine if this woman met his exacting standards. But from what he read, he was not so sure she was the right one for the job.

Jack studied her resume for a few more minutes, familiarizing himself with her background. Closing the file he checked himself in the mirror of his private bathroom, smiling at the reflection staring back at him.

He adjusted his red tie against the baby blue shirt and then pulled the soft grey suit coat off the hanger. Looking at his reflection once again, he was satisfied that he was ready for the interview.

Walking to the conference room, he greeted his staff on the way. Opening the door he saw a young lady sitting on the leather cushioned chair. When she turned her head up to see him entering, he instantly felt something good about this woman.

He smiled at her and extended his hand. "Good morning Ms. Mays. I'm Jack Connors and I am very pleased to meet you." As he settled in the leather chair across from her at the large conference table, he took in her lightly-tanned skin and alluring hazel eyes that sparkled.

Opening the folder, he glanced up and noticed her ample breasts snugly hidden by her tight white blouse. The gold hoops dangling from her ears, caught his attention as he cleared his throat. She had the look of what he was seeking but he still was not sure she was qualified to do the tedious work required of an executive secretary. Giving her his warm comforting smile, he asked her, “Tell me a little about yourself Ms. Mays and why you think you are qualified for the position?” He concentrated on her eyes as he waited for her response.

 

[Aluris]

It had been three months since her last placement. Three. And that had only lasted for a month itself... a temp receptionist job, covering for someone's maternity. Cassie looked in the mirror at herself, smearing another layer of dark brown eyeshadow over a closed lid with a sense of desperation. I am smart. I am capable. I can get this job. It was something she wasn't... exactly qualified for, but still underneath her - a personal assistant? She'd worked herself into a ton of debt and a lack of any social life all the way through college to be some airheaded secretary?

How the mighty have fallen. With a gentle pull at a curl of hair, Cassie sighed and pinned it back in place behind her ear. Not too long ago, Past Cassie would laugh at Present Cassie. This was the equivalent of grovelling in the dirt for her and the standards she'd originally set for employment. By now she'd have expected something... more.. qualified.

Beggars can't be choosers - Cassie reminded herself of that as she primed another slick of lipgloss onto her lips, swallowing back her remaining doubt with a purposeful gulp. The rent was due again in three months and without another set employment, however temporary, she'd have to move back home. And she didn't want to be yet another helpless ex-student who needed to run home with their tail between their legs because they couldn't make it on their own.

+++​

"Good morning Ms. Mays. I'm Jack Connors and I am very pleased to meet you."

Two hours later, and Cassie had been waiting for the interviewer to be free for only a few minutes. The woman who had greeted her had been very pretty... she already felt intimidated, her casual-smart outfit outshined quickly even by the main receptionist at the door. Perhaps she'd underestimated exactly how high the standards would be here for a new employee.
However, she did her best to wipe all of that doubt off of her face as she shook the hand of Mr. Connors. With a curt nod, she gave a similarly polite, reserved smile and did her best to make her handshake firm, but not clingy. Her mind flickered back to when her old college lecturer had made them practice this on their last day, joking that a good handshake could be the make or break of their career. In retrospect, perhaps that hadn't been much of a joke...

“Tell me a little about yourself Ms. Mays and why you think you are qualified for the position?”

"I'm a graduate of Modern History." Cassie began, then wanting to bite down hard on her tongue. He'd already know that. "I'm proud of my work ethic, attention to detail, and the importance I place on teamwork and.. and on meeting stated deadlines."
Wow, let's just fill all of the empty spaces in the traditional interview answer box, Cassie.
"I'd bring enthusiasm to the position, an earnest set of values to contribute to the company, and I'm not bad at making coffee!"
Okay, that was just painful.
Cassie smiled as genuinely as she could, although as his eyes flickered briefly down to the table, she felt a clenching in her stomach.

 

[Rocket1010]

Cassie's interview

Jack listened to the girl recite what he already knew and wondered how in the world she thought she could handle the job of executive secretary. He was looking for a woman who knew the ropes of taking charge of his busy schedule, keeping him on track from meeting to meeting, go with him on trips to the other offices which would entail overnight stays, and one more important thing, be at his beckon call for extracurricular activities to satisfy his sexual appetite.

Some of the other applicants had impeccable resumes, working for other CEO’s and looking for a chance to move upward in their career. While others were not so qualified, they also didn’t portray a certain sexual awareness he was looking for. He had a sense that this woman, Cassie Mays, had some potential but he wasn’t convinced that she was the right one for the job. She was telling him all the standard things they tell you in school about how proud they are of their work ethic, their attention to detail, and teamwork. All the other candidates had mouthed the same things and Jack wondered if any of them had a thought of their own. He was looking for someone not only qualified but also an ability to carry out orders and to think proactively.

Jack let out a soft chuckle when Cassie told him she was not bad at making coffee. “I don’t think you have to worry about making coffee Ms. Mays,” he said noticing how the dark brown eye shadow brought out the sensual look in her eyes. ‘Hmmmm maybe there is some hope for her,’ he thought as he remained silent, taking in her figure and facial features.

It was evident to Jack that this girl didn’t really know the responsibilities of an executive secretary. For a moment he wondered if he should waste his time telling her about the position or just dismiss her, thanking her for the job, and telling her they would be in touch with her about the position. He saw her eyes glance down to stare at the table when he lifted his wrist to look at his watch. He could easily have looked at the wall clock. Looking at his wrist watch was intimidating to the other person and usually meant the end of the interview.

He didn’t have another meeting for about an hour so he cleared his throat and saw the young woman pick up her head. “The job is so much more than just being a secretary, answering the phone, typing letters, and fetching me coffee,” he said seeing her eyes sparkle with interest.

The title is executive secretary and whoever I hire for that position answers to me and only to me. I am a very busy person with tight schedules for meetings and conference calls. I need a person who will be loyal to me and do my bidding no matter what I ask. The position calls for that person to be at my beckon call day or night, travel with me to our other offices, and attend conferences as my right hand person. I expect a lot out of that person and they will be compensated well.

Jack left off the part about his fetishes that would be a requirement for the position. But he didn’t see any reason to bring it up to Cassie. Besides whoever he hired, they would soon learn that he was very good at blackmail and had no doubt they would bend to his wishes.

“So as you can see Ms. Mays, this position is so much more than just making coffee,” said with a smile. “You probably knew when you came in this morning that you are not all that qualified for the position. But you are here and you are to be commended for taking the first step. b After hearing what is to be expected, what makes you qualified for the position?”

Jack sat back in the black leather chair and watched her expression change to one of thinking. He again took in her body and wondered what she would say to convince him.

 

[Aluris]

“I don’t think you have to worry about making coffee Ms. Mays”

A long pause followed this, in which Cassie readjusted herself on the chair awkwardly. So much for her joke. It was bad anyway. He had laughed; it made one wonder how much falsifying his reactions to things was a part of his job. For some reason his exact job title escaped her memory now...
Cassie was about to clear her throat and continue the interview when his eyes looked to his wristwatch. A feeling of foreboding sunk onto her shoulders, and strangely, she had to fight the urge not to just burst into tears. Had she really put this much hope on the job? It was a fact that she had no Plan B if this went wrong. Her hands scrunched the material on her lap, eyes flickering to the shined surface of the conference table. Without really meaning to, she began planning how she'd get to her parent's house. I'd need to take two trains... I have a lot of clothing, so I'd need to look into some sort of van hire, so maybe I could travel with the van. It'd be cheaper. Perhaps I could even drive it? Some places let you-

Then Mr Connors cleared his throat, and Cassie jerked her eyes back up with an embarrassed nod.
“The job is so much more than just being a secretary, answering the phone, typing letters, and fetching me coffee.”
Cassie pursed her lips. That was what she assumed a PA would do, after all. General organisation, and ensuring there was some sort of 'holding of the frontlines'... meaning the main boss just dealt with the necessary items. Or played golf all day. She listened carefully to the outlined work... okay, well. Who knew PA jobs could get that intense? It did sound like a challenge, perhaps something to stick out for a year and then put on her work record, but...

“You probably knew when you came in this morning that you are not all that qualified for the position. But you are here and you are to be commended for taking the first step. After hearing what is to be expected, what makes you qualified for the position?”

Her mind. A blank. Well.
"I can tell you, Mr Connors, that my loyalty will never be in question." Cassie inserted a smile, leaning forward onto the desk as if sharing a secret. She was told once that it incited trust with someone. Or something.
"I am looking forward to being dedicated in a position which I feel I can grow in. I feel this is that position and I would prove that, given the chance. Being on call is of no problem to me and I would take the initiative to make sure you want for nothing during the work day."

 

[Rocket1010]

Jack hires Cassie

Jack sat in the plush leather conference chair watching Cassie very closely. He knew she was not probably qualified but there was something about her that intrigued him. He thought of Jeanette, his last executive secretary and how inexperienced she was when he hired her. But it didn’t take long for him to assert his dominance over her. Once she got a taste of his sexual fetishes, Jeanette became an insatiable slave to his wishes and desires. Jack had a feeling Cassie may be cut from the same cloth.

He thought she acted a bit desperate in answering his questions and so he gave her another chance. He didn’t know what she was going to say to convince him but when she leaned forward, telling him her loyalty would never be questioned, he gave her a smile.

He listened as she told him she would be dedicated, wanted to grow in this position, and would prove it if given the chance. She mentioned being on call would not be a problem but it was the last part of the sentence that intrigued him ….. she would make sure he would want for nothing during the work day.

Jack sat back as if contemplating her words thinking about only the last part. He wondered if she would run away if she knew what her words really meant. Jack had certain fetishes and she would play a starring role in having those fetishes satisfied.

He let the silence grow between them, wanting to make her feel uncomfortable. Watching her fidget gave him a thrill and he loved the power he had over his employees and he could feel the power he had over Cassie. There was no doubt in his mind that if he hired her, he would blackmail her and bring her into his world of sexual adventures.

The way her eyes darted from her hands scrunching the material of her dress to the table and then to him, told him she needed this job. He didn’t know her personal problems but she was acting like a person that needed some income. He knew from her address on the resume, that she lived in an apartment. He surmised that the rent was probably more than she could handle since she had not had a job in three months according to her resume.

The silence was growing tenser and Jack finally let a smile form on his face. “Listen Ms. Mays I’ll hire you on a temporary basis, call it a probationary period if you will. Your salary will be $50,000 a year to start and after the probationary period, if you do well, it will increase. Also after the probationary period, you will be eligible for health insurance and the company’s retirement plan.

Jack saw the look of relief on her face and then a joyful expression. I expect you to start tomorrow morning and be here sharply at 8 am. If you are late don’t bother to come in,” he added giving her an incentive to get to the office early. “Are you ok with those provisions Ms. Mays?” He knew it may be the last time he would call her by that salutation. Soon he would be calling her his slave, slut and whatever he wanted but for now it was Ms. Mays.

 

[Aluris]

A job? An actual position? Cassie could barely keep the smile from her face, although she quickly quieted it to a more polite expression, a firm nod of the head answering some of the later points... I have to get in early, make that first good impression. Wait, was that him offering $50,000 a year? For a PA job?! With health insurance?-
Realising that Mr Connors was waiting on her reply, Cassie then jolted her head into another nod, fixing her hair self-consciously.

"Thank you very much for the opportunity, sir. I'll be here tomorrow."

Then she stood, assuming the interview was over - after all, what else was there to cover? By him looking at his watch, it seemed he was in a hurry... after his agreement to her having the job, he began to check his watch again, which only made Cassie even more flustered.
"I-I'm sorry for taking up so much of your time." She quickly added, smoothing down her clothes as she spoke. There was no harm in making sure he knew how much she appreciated this, after all. "Is there anything you'd like me to bring tomorrow, or will any additional equipment be provided?"

 

[Rocket1010]

Jack leaves Cassie with Ms. Jennings

Jack smiled at the young lady who, he could see, was very excited about being offered the position of executive secretary. He wondered if she really knew what she would be doing for him, if she would be so excited or would she bolt out the door.

Looking at his watch, he saw he had a few more minutes and was a little surprised when Cassie got up from her chair. He listened to her apology about taking up so much of his time, watching her smooth out the wrinkles of her dress. He almost laughed when she asked if there was anything she should bring to the office tomorrow or if any additional equipment would be provided.

His first thought was of her naked and lying across his desk, or maybe under the desk, pleasuring him. And the mention of equipment instantly brought to his mind the equipment he would use on her later. Standing up, he gave her a soft smile, took her small hand into his, and nodded. “You are not taking up my time and if you work out in this position, we will be spending a lot of time together.” He wondered how her lips would feel against his. They looked so inviting and tempting but that would have to wait for another day.

“As for any additional equipment, we have everything you will need to do your job efficiently and effectively,” he added thinking of the fur lined cuffs that he had in his desk drawer ready for use. Jeanette, his last executive secretary loved to wear them and Jack wondered as he held her soft hand if Cassie would feel the same way.

Jack picked up his folder from the conference table. “I have a meeting I have to get to. Please see Ms. Jennings for some papers to be filled out before tomorrow and any other thing else you will need to know. I’m looking forward to having you on staff,” he said walking with her to the door.

When they arrived at Ms. Jennings station, Jack informed her that Cassie was the new hire and she should send out a letter to all the other candidates telling them the position was filled. “See you tomorrow morning at 8 and not a minute later,” he told Cassie and then he was gone.

“Well Ms. Mays congratulations. You must be very special because Mr. Connors has some very exacting and strict rules. You must have impressed him greatly. Now as for tomorrow. You are to be here at 7:45 sharp and ready to meet Mr. Connors at 8 for the daily briefing. The coffee is already made and you are required to take him a cup when you meet with him. As for dress, Mr. Connors wants his executive secretary to look sharp at all times. He has some very important clients that you will need to impress and if you impress them, you will impress Mr. Connors. Here is a pictureView attachment 1768240 of what he may deem to be appropriate. As you can see I too wear the same type of dress.”

Ms. Jennings looked at Cassie and smiled. “I think you will do very nicely.” Picking up a blank check from her desk, she handed to Cassie. “Use this to go to Fredrick’s Boutique. They have a large selection of garments and undergarments which will do nicely for your new position. You may buy whatever you need for your new position. If there are no questions, I will see you promptly at 7:45 am tomorrow morning.”

 

[Aluris]

Cassie couldn't help but breathe a sigh of relief as she watched him walk away.He's so nice, she thought idly. It'll be easier to work such an intense position with an understanding boss. Another jolt of excitement rang through her as she thought that - she was employed! The woman had to stop herself from punching the air as she looked at the secretary expectantly, although she couldn't hold back a wide smile. She probably looked crazy, but at that moment, she didn't care. Just imagining the phonecall to her parents later to assure them of her continued independence was sending her stomach into light spirals of joy. Her roommate would be relieved too...

The receptionist - Ms Jennings - was polite, and just as nice, although Cassie got the instinctive feeling that she was up against a standard she just couldn't reach. The smile faded as she was handed the blank cheque - it was... intimidating, in a strange way. She hadn't even shopped at a boutique before and now she was being told to buy a whole new wardrobe for a simple PA position. Well, it doesn't seem too simple, but still...

"Seven forty-five tomorrow. Thank you, ma'am." Cassie bowed her head, backing away before finally leaving the building. She felt a little like a mouse scurrying away from the fox's den, her initial jubilation at the successful interview now dampened slightly by the task ahead. Before this, she would have said she was quite fashionable, but now she wasn't sure if her tastes matched those of the personnel in her new workplace.
As she was thinking, a light rain began, forcing her away from the thoughts and instead racing for one of the city taxis. It was a relief as the car pulled away from the sidewalk; Cassie did not resist taking a final look out of the window as the office complex faded into the distance. Then it was just her and the cheque, the flimsy piece of paper being flipped over and over in her hands as the driver smoothly maneuvered the streets.
"Any plans?" He asked, glancing in the mirror.
"No." Cassie said absently, her eyes re-reading the cheque details as she fidgeted. "I... I just got a job, but I need to buy new clothes for it."
"Expensive place to get clothes." The driver shrugged, referring to her chosen destination.
"I'm working for a place that demands such things now, I guess." Cassie grinned, although it faded quickly. "I have to at least try to look the part."
Their conversation drifted to discussing the weather, the driver then mentioning his son returning home from a work trip later that day at the local airport. Cassie wrinkled her nose at the mention of that... she'd always been terrified of flying. The last time she'd had to was at a schooltrip a few years ago, and she'd done her best to avoid them ever since. The mere memory of clutching at the armrests with a face white as a sheet was bad enough.

The rain had stopped by the time Cassie left the taxi, and she was just able to pay him with what was in her purse. The boutique stood before her - another challenge, almost like a second interview. Just walking in made her feel dowdy and unprepared. The assistant who met her was like a model - high cheekbones dusted with bronzer and blusher, bright eyes ringed with thick mascara, her tight body encased in a thin strappy dress. Cassie wanted to hate her, but she was so nice, she couldn't help but smile despite her own misgivings.

"I'm not really sure what I want." She confessed, gesturing around the store helplessly. It was small, but it was stacked with organised shelving units and racks of clothes, with every inch of other available space shined and bright. "I've been told to get outfitted for a new work placement, but..."
"Did they give you any examples?" The assistant twittered, her whitened teeth glinting.
"Actually, a picture..." Cassie brought it out, giving it over with a hesitant smile.
"Oh, we have quite a few things in this style. I'll give you two dresses, three skirts and shirts, and a pantsuit to begin with, and we can go from there?"
"Uhm, uh, sure."
"Right this way!"
The assistant - who later introduced herself as Michelle - had such enthusiasm for the task that it was contagious, and soon Cassie had relaxed, holding up various outfits to her body for feedback, the two of them flicking through so many possible clothing options that the woman's head began to spin. Skirts, shirts, blouses, cardigans, different dresses... so many styles... pantsuits, belts, jewellery...

It took three hours in the end, but Cassie left with seven outfits - three dresses, one almost identical to the picture but in a more reserved blue colour, and then one longer off-white one but sleeveless, and then the third had long sleeves but a shorter skirt, taking Japanese kimono inspirations for the dark red and white patterns. Then there was three skirts - all black, with one off-white blouse, a tight pink shirt, and then one red, low-cut shirt that Michelle practically insisted she should have. Finally there was two pantsuits - Cassie wasn't sure if they were allowed, but they fit to her body perfectly, and the pair of heels that came with them added a good two inches to her height. She was in love.
"How much-"
"I'll just write it on the cheque, honey." Michelle giggled, flapping her elegant fingers at her casually. "You're going to blow them away. Come back any time!"

+ + +​

Half seven the next morning, and Cassie was stood in front of her new workplace, her hands sweating. She hadn't even told anyone about the job yet - she'd decided she would see what it was like for the first week, if she lasted that long... her confidence had dropped the night before as she'd tried out her clothes in secret, smoothing out the wrinkles anxiously in her bedroom mirror. She did not look as glamorous without the extensive lighting and now she was worried that it was a bit... much. The position was PA, not supermodel...
It was too late now, however. She was dressed in the reserved blue version of the dress Ms. Jennings had showed her the day before, hair pinned back into a curled bun. A small black handbag was slung over her right shoulder to carry make-up, phone, purse... she felt she was going to a party, not to work. Cassie tugged nervously at the back of her black heel before walking in, back straight, trying to give off as confident an impression as possible.

 

[Rocket1010]

Jack begins to set the trap to blackmail Cassie

After Jack left Cassie in the capable hands of Ms. Jennings, he spent the rest of the day in meetings and phone conversations with prospective clients. But throughout the day, Jack’s mind wandered to the young woman he hired as his executive secretary. He smiled during one meeting as he thought about her facial expression when he offered her the job. He could still see the suppressed grin as she tried to conceal her excitement. One of his best clients, Adam Goings, asked him why he was smiling. Jack was not about to tell them about Cassie yet. Adam would find out soon enough about the young employee so he gave him some lame excuse about a joke he heard earlier in the day.

That night Jack dined out with some clients and they asked him about a replacement for Jeanette. They knew Jeanette and all agreed that she was going to be missed. Jack laughed at their comments knowing they were anxious to see the new employee. “Don’t worry boys, when I the time is right you will all have a chance to meet my new executive secretary,” he chuckled knowing that they would have their tongues hanging out when they got a look at Cassie. They tried to pry out some information from him but he wanted to keep them in suspense until he was sure Cassie would work out. He had a feeling she was going to work just fine.

*********************************************************

In the morning, Jack got ready at his usual early hour and was in the office by 7 am. He liked being the first one in the office as it gave him a chance to think about his hectic schedule. But this morning his mind was far from the schedule of meetings and phone calls. It was on Cassie and he wondered if she would take Ms. Jennings advice about proper attire.

One thing he pondered was how long he would keep Cassie in the dark about his fetishes. With Jeanette, he introduced her to his cravings within the first week. She hesitated at first but he knew all the right buttons to push, telling her if she didn’t want the job, she could look elsewhere. Jeanette was desperate at the time with a husband unemployed at the time, she gave in to his fetish desires. He missed her now as he awaited the new employee. ‘Would she be easy to blackmail,’ he thought as he looked out the window to the street below.

A smile slowly crossed his lips as he watched Cassie on the street below, standing staring at the building. ‘Should I give her a few days before I start the blackmail or should I start today,’ he mused as he watch her glance around and then walk to toward the front entrance. One thing for sure; he didn’t want to scare her off. It was better to let her get her feet wet before he sprang the trap. He was pretty sure from her reaction yesterday that she needed this position. He let out a chuckle as he went to his desk, “let the game begin,” he said out loud to the empty office.

He was ready over a contract when there was a soft knock at the door. Looking at the large ornamental clock on the wall, he saw it was a few minutes to 8. One thing he liked was punctuality and he was pleased to know that Cassie was right on time. Putting a big smile on his face he stood and announced, “Come on in Cassie.”

His eyes and facial betrayed the look on his face. ‘She looks amazing,’ he thought as she entered the room with the stenographer’s pad Ms. Jennings gave her. “Good morning Cassie. I see Ms. Jennings gave you some idea of what our dress code is around here,” he said taking the hot cup of coffee from her hand. He admired the way she looked in the blue dress and her hair pulled back into a bun. A vision of him pulling her hair as he kissed her deeply on the lips entered his mind. Trying to push those thoughts away he smiled at her.

“That’s good and I see you remembered the coffee,” he added motioning her to sit in one of the large leather guest chairs. “We have a very busy schedule of meetings and other things so let’s get started.” Jack walked around his desk to sit down. “This is a letter to Adam Goings at First Financial,” said looking at his new employee and wondering what she would think when she became his personal slave rather than personal secretary. Then he stopped and gave her a startled look. “I’m so sorry Cassie how rude of me not to ask if you have any questions. Is there anything you want to know before we begin?”

 

[Aluris]

Ms. Jennings had been the one to greet her, arriving mere minutes after Cassie had in the lobby. The elevator ride to the top floor had been slightly awkward, the older woman checking her phone and tapping out message after message... it had been difficult to resist looking at what was taking her so long to organise, but in the end, Cassie decided it was not worth losing respect simply over her curiousity. Besides, it was probably something boring, like administration...
"Did Mr. Connors ask you to come in early?" The woman inquired as they both stepped out at the top floor.
"Yes, ma'am. Well, he mentioned that it would be a good idea."
Ms. Jennings hadn't said anything to that, only nodding and then walking around to her own desk. The way she carefully set down her handbag to then check various notebooks around the monitor made Cassie feel she was watching a morning routine long set in stone.
"He likes his coffee just after he gets in." Ms. Jennings suddenly said, sounding distracted. "You'll also need one of these writing pads. You do get a lunch break, but it's at Mr. Connor's discretion."
"Of course." Cassie replied primly, watching as the woman scurried about behind her desk, preparing for the work day. She felt even more out of place - having nothing to do, whilst there were people getting to their day's work right in front of her - but it would not be long before she had her own work list. At least from the sound of it. "Do I just..."
"The coffee machine is in the lounge room, with all the condiments. You'll also have to visit back here for more formalities throughout this week, on Mr. Connor's orders."

Cassie didn't really like the idea of that - orders. Although she had assumed as much, that he would be demanding. He hadn't exactly glossed over what he expected from his new hire after all.
With another forced smile, Cassie shuffled herself away from the desk, the new writing pad stuffed under her arm as she made the coffee. There weren't many people on this floor... at least, not in the lounge. Perhaps their offices had their own coffee makers, or they were on the floor below. She made a note furtively to find out where everyone else was based (at least, the main people) later on in the day.

+ + +​

Well... Mr. Connors had reacted well to the coffee. He'd taken it at least. Cassie stood in front of him as he paced around to his desk, sitting down comfortably to look at her properly. It was at that moment she became horribly aware of her posture, and as he spoke, she subtly began to correct it.

“I’m so sorry Cassie how rude of me not to ask if you have any questions. Is there anything you want to know before we begin?”

"N-no, sorry. Sir." Cassie blurted, her nose wrinkling at how her voice sounded - so squeaky, so unprepared, unprofessional. "Ms. Jennings has been lovely so far in telling me the basics, and I'm eager just to get started properly and learn on the job. Although...."
The woman hesitated, although she tried to keep her composure as she continued.
"Is there anything your old hire left? Notes, or records of her work here? I think it'd help me learn names and other details of my expected role."

 

[Rocket1010]

Jack smiled at his new employee as she settled into the leather chair, pad and pen in hand ready to go to work. He studied her as she told him in a nervous squeaky voice that Ms. Jennings had filled her in on most of her duties. When she hesitated he could tell she was trying not to show the nervousness that was probably running rampant in her. He took another moment, as if thinking, but he was really looking at her after she asked if his past secretary left for her to use. Taking in the shape of her breasts pushing against the dress, he smiled. “No. There are no records or notes that Jeannette left, except the roll-a-dex of client names, addresses, cell numbers that may be helpful. If she only knew that Jeanette’s duties were so much more than just taking dictation.

The chuckle from his lips was soft as he thought of the word “dictation.” ‘She did a good job of taking notes and his dick,’ he mused silently. Here in front of him was a supple young woman who was about to learn that she would obey his demands or lose her job. But when would be a good time to spring this on her. The sooner the better but not on the first few letters but she would find out by the end of the day.

“Ok Cassie let’s get started on the letter to Mr. Goings and then we have one for Mr. Thompson.” Without waiting for her to speak, Jack began dictating the letters. He purposely he talked slowly but never stopping and asking if she was keeping up. That was half the fun, reading the errors and then reprimanding her for making the mistakes.

When he finished dictating the letters, he saw a look of confusion on her face. “Ok Ms. Mays,” please type these letters and have them on my desk within the hour. We have a meeting with a potential client and I expect you to be in on that meeting taking notes.” He turned his attention to some papers on his desk and then looked up to see the young lady looking at him. He loved this initial part of her training. “That’s all Ms. Mays,” he said picking up the phone and pressing a button. “Ms. Jennings please get Mr. Reynolds on the phone immediately.” As he waited, a smirk crossed his lips as the young woman got up and walked out of his office.

Jack knew she was not going to get everything correct. And even if she did, he would find something to reprimand her. ‘It is only a matter of hours now Cassie,’ he thought as the sound of a deep male voice came on the other end of the receiver.

 

[Aluris]

“No. There are no records or notes that Jeannette left, except the roll-a-dex of client names, addresses, cell numbers that may be helpful."

Well, thanks Jeannette, Cassie thought. Nothing like an unhelpful ex-employee to give a more difficult start to a position. Even in her temp job she had left notes... well, the client names and their contact details were something. She made a mental note to look over that as soon as her initial meeting with Mr. Connors was over-

“Ok Cassie, let’s get started on the letter to Mr. Goings, and then we have one for Mr. Thompson.”

Cassie looked up, then forced to scramble for her pen as he immediately began talking. No real warning at all, and no breaks - her hand was cramping from the awkward angle she was writing at only minutes in, her writing becoming tiny and scrawled inbetween the lines. Words began to blur, and Cassie fought down the urge to ask for a pause, or clarifications... it would look unprofessional, and he was obviously going at the pace he expected from her. It was with a quiet, almost silent gasp of relief that the exercise finally finished; Cassie even felt a speckling of sweat upon her brow.

She didn't know what to expect next, but whatever it had been, it was not what actually did happen. After a brief glance at her up and down, Mr. Connors had then dismissed her outright, barely looking at her afterwards as he contacted Ms. Jennings. Cassie had sat there in numb confusion before he'd had to direct her out of the office verbally again. Now sat at her own desk in the next room, she cringed openly at reliving those last few moments... her cheeks darkened just at recalling his expression at seeing her still sat there. Stupid, stupid Cassie! She thought as she typed away, her fingers stumbling over the keys as she tried not to linger too much on her embarrassment. Her first impression had gone terribly. And now, not even these letters even sounded right. Panicking, Cassie made minor adjustments so they would flow better, but now it didn't even sound like Mr. Connor's original wording. Shit. Shit!

Leaning back on her chair, Cassie sipped at her coffee and tried not to wish it was something alcoholic. From here she could see Ms. Jennings, quietly getting on with her work... Cassie thought about asking her for help, but discarded the thought immediately. No, she was just going to have to suck it up. Perhaps he wouldn't even notice. He'd probably already forgotten her slowness to depart from his office.

It was with that in mind that Cassie brought the print-outs to his desk with a bright smile, lying them down before then standing there with her hands folded in front of her, notepad tucked under her arm. The picture of the listening secretary prodigy - so she hoped.

 

[Rocket1010]

Jack admonishes Cassie and gives her orders

He was looking over some notes for the upcoming meeting when he heard the soft knock on the door. Looking at his watch seeing it was 50 minutes from the time Cassie left his office brought a smile to his face.

That smile was still on his face when she entered and as she walked to his desk, he took in the way her hips swayed sexily in the tight dress. He wondered what she was wearing underneath the dress as he looked up to see her bright smile.

She didn't say a word as she laid the letters in front of him to review. He saw her hands immediately move in front of her, clasping each other as she waited dutifully for him to say something.

"Well let's see how you did Ms. Mays," Jack smirked knowing she was not going to get the letters right. He thought of Jeanette and how she used to record him so she was able to listen afterwards. Jack knew that later he or Ms. Jennings would suggest a tape recorder but for now he wanted to have his fun with her.

"Hmmm .... mmmmm I see," he mused as he picked up his red pen and began to make changes, scratching out words, adding new ones. "I didn't know I said this," he added with a chuckle.

When he was done with one letter, he placed in at the front of the desk so she could see some of the changes he made to the letter. Taking the other letter, he did the same thing, muttering and smiling as he marked it up in red. It was as if he were the professor and she the student and he was marking up her homework.

"You did a passable job Ms. Mays but there are a lot of mistakes and I don't like mistakes." He paused for a moment letting his words sink in. "We have a meeting in 30 minutes. Please make the changes to these letters before then."

Handing the letters to her he added, "And by the way Ms. Mays when you have made all the corrections you are to proceed to the women's room and remove your panties. I want them on my desk with the letters before the meeting."

Jack saw the look on her face and quickly added, "Do you have a problem with my requests Ms. Mays because if you do then your employment is terminated." It was up to her if she wanted the job and he had a strong feeling she was going to give up her panties. This was the first small step of her employment and becoming his personal slave.

 

[Aluris]

"You did a passable job Ms. Mays but there are a lot of mistakes and I don't like mistakes."
Cassie kept her expression neutral, although her stomach clenched hard at the comment. Well, she knew she had made mistakes, but she had thought... well, it didn't mean what she had thought. He didn't like it. Her earlier enthusiasm dropped like a stone; it was all she could do to keep herself from bursting into tears right in front of him. Pull yourself together, Cass.

She mutely took the letters from him, her eyes flickering to the carpet beneath their feet. It was nicely hoovered, clean, she mused. Probably a nightly maid-
"And by the way Ms. Mays, when you have made all the corrections, you are to proceed to the women's room and remove your panties. I want them on my desk with the letters before the meeting."

Cassie jerked her gaze back up, so fast it actually hurt her neck. What?!
"Do you have a problem with my requests Ms. Mays because if you do then your employment is terminated." Mr Connors continued, his hands clasping together on the desk in front of him. There was the hint of smugness in his tone, his eyes crinkling as he stared at her intently. This was not the first time he'd requested it from someone, Cassie's stunned mind thought wildly. Perhaps this is why he employed me in the first place. Or is this a test of professionalism? Making sure I won't just sleep my way to the top?... if that was the case, why would he threaten her with termination?

The silence extended between them, and Cassie felt her cheeks and neck flush with a soft crimson colour.
"You're dismissed, Ms. Mays. Think wisely on your decision." Mr. Connors ended, waving his hand at her before turning his gaze back to his monitor. Cassie nodded, silently taking her leave with the letters pressed to her chest so hard that the paper wrinkled. Every footfall felt heavy, and her stomach was now a heavy stone somewhere at the bottom of her abdomen. Even as she reached her work area, she was already kicking herself for not saying something - anything! Now she was left with her own judgement... whether he meant it, or not. Whether she really would be fired if she didn't do it or if it was the other way around.
Pulling her hand through her hair, Cassie looked back and forth from the door to Mr. Connor's office to her desk... before she remembered that she still had to make corrections to his letters. Shit. Rubbing at her brow with the back of her hand, she forced herself to focus on correcting the mistakes, her eyes squinting at the monitor. She was simply happy for that fifteen minutes to have a break from... well, freaking out.
It was not to last.
Glancing at the clock, Cassie realised with a shock of indecision that there was only five minutes left until the deadline that Mr.Connors had set. Another glance at his office - he hadn't left. He was probably watching his clock too. Perhaps even the door, to see if she'd go to the bathroom before walking in.
Not even here a day and her whole job was waiting on one decision! And one that made her feel pretty conflicted... if he really did want them, then why? Cassie shook her head. She'd really rather not think of that right now.

Standing from the desk, Cassie left the new print-outs on her desk before making her way slowly to the bathroom, the door looming up in front of her far too soon. From there it was a simple action of finding a free cubicle, then slipping her panties down her thighs, over her shins, folding them up in her palm carefully before making her way out. A look in the mirror showed how flustered she looked, but it was the least of her problems right now.
Slipping the panties inbetween the sheets of paper, Cassie walked into Mr. Connor's office as confidently as she could, lying down the work on his desk with a huff of finality about it.

"Shall I wait outside until you're ready to go to the meeting, sir?"

 

[Rocket1010]

Jack teases Cassie in the meeting

When Cassie left his office, Jack sat back, smiling at the thought of her without her panties. He relished the confused look on her face when he told her he wanted the letters along with her panties. The question he asked himself as he looked out the large windows, ‘would she or wouldn’t she take off her panties?’

Looking at the clock on the wall, he saw she had 25 minutes to get the letters retyped and her panties off. If he guessed right she was probably arguing with herself if she needed the job or not. The way she jumped at the offer yesterday indicated she needed the job. Besides the offer of a lot of money and benefits would make it hard to turn down. A boat was chugging down the river below as he thought about Cassie. She probably told all her friends and family about her new job and how would she be able to go back to them and tell them she was terminated after one day. If she left, he already had another story, fabricated of course, as to why he had to let her go and it had nothing to do with wanting her panties.

The panties were a test. If she took them off and presented them to him, he knew she wanted the job and would do almost anything to keep it. That was important to Jack. It meant she passed the first small test on becoming his personal slave. The next test would be immediate as he wanted to know by the end of the day if she was the right person for the job. If she came back with her panties on, then he would quietly dismiss her and start looking for another candidate.

The intercom buzzed and Ms. Jennings told him the marketing staff were in the conference room and ready for the meeting.

“Where is Ms. Mays?” he asked looking at the clock, seeing she had about five minutes left before the deadline he set.

“I just saw her heading for the women’s room,” she replied. “Do you want me to go fetch her?”

“No that will be fine Ms. Jennings,” he said smiling and almost letting out a laugh.

Gathering his papers for the meeting, Jack looked up when his office door opened and Cassie walked in without knocking. The letters were tucked between her arm and breasts as she strode to his desk, staring straight at him. The color on her cheeks were a bit pink as if she were shy and he wondered what she had decided. When she practically threw the letters on his desk firmly, he could tell she was uncomfortable. ‘That is what I want Cassie ….. you to be uncomfortable right now,’ he thought as he lifted the top letter seeing her white panties lying on the other letter.

"Shall I wait outside until you're ready to go to the meeting, sir?"

“No that won’t be necessary Ms. Mays. You may remain standing as you are until we are ready to leave,” he said with a smile picking up the soft silky panties. “Mmmmm very nice Ms. Mays. “You have good taste in underwear,” he added holding up the panties as if inspecting them. Jack glanced at Cassie and saw her moving from one foot to the other, fidgeting as he looked at the silk panties.

He wondered if she was ready for the next test when he stood, tucking her panties into the top drawer of his desk. “We have a meeting to attend Ms. Mays,” he said coming around the desk. Putting his arm on the small of her back, he guided her to the door. “We don’t want to keep the staff waiting.”

The pair stopped at Cassie’s desk to pick up her note pad. Heading to the conference room, he told her, “The marketing team will be making a presentation and you will sit by me and take notes.” He didn’t wait for her to answer as he swung the door open and the room was filled with twelve marketing representatives all seemingly talking at once. When they saw Jack, there was an instant silence as he and Cassie entered the room.

Jack guided Cassie to the head of the long conference table and took a seat. “Alright everyone let’s get this show on the road. I want to introduce you to Ms. Cassie Mays who is my new personal secretary.” There were nods all around the table and some of the women stared at her longer than the others.

“Mr. Jackson I believe you have the honor of presenting the current marketing report.”

“Yes sir,” Robert Jackson replied and immediately turned his attention to the full height screen. As he began his spiel, all heads turned toward him, away from Cassie and Jack, listening as he began detailing the marketing efforts.

Jack leaned over to Cassie and whispered, “Please take good notes.” His hand moved under the table and landed on her thigh. He felt her jump and a little squeal came from her lips, but nobody turned their heads in their direction. “I hope you don’t mind,” he said moving his fingers lightly over her naked thigh, pushing the hem of her skirt higher until they brushed lightly over the outer lips of her sex.

 

[Aluris]

The CEO had an unexpected reaction to her brave declaration of following his first order to the very letter. Cassie had expected many things - perhaps her immediate dismissal, of course - or some further perversion at the very least, but instead he had simply stored her clothing for later, and had hastened her to the meeting. Mr. Connors had turned back from leering boss to brusque superior in less than a few seconds, and Cassie felt very light-headed and strange as she scurried after him down the corridor. She wasn't sure if she had won favour with him with her action, nor if he was simply amused, or whether he was irritated and simply needed her just for this meeting. On top of all of these thoughts she was horribly aware of how bare she felt underneath her skirt.

None of this helped her as Mr. Connor's waved her into room, Cassie only barely aware that he had spoken to her before he'd opened the door. Twelve curious pairs of eyes fell upon her as she was briefly introduced; quickly she had to drop the pad into a more professional stance instead of holding it tightly to her chest like a nervous schoolgirl. With a smile and a nod she acknowledged their attention, then quickly settling into her designated seat as the speaker took the stage. It was good to have a speech to focus on, Cassie setting down the pad and focusing on the notes as she had been instructed. A part of her calmed - this was something she knew how to do. No complications.

It was not long after the speech had begun, however, that her boss decided to make complications himself. As Cassie nodded along to some of the points (mostly out of politeness), she felt a sudden pressure upon her leg. A squeal she mostly stifled was luckily unnoticed by her colleagues, but she gave an indignant look to the man next to her - Mr. Connors. His hand smoothed over her thigh with directness that put to sleep any urge she had to speak up. Feeling her cheeks warm, Cassie looked back to Mr. Jackson with what she hoped was believable focus, trying not to think about the fingers suddenly probing at her folds. Had this been his plan all along? Cassie set her mouth into a thin line, then carefully folding her legs over to block his access. She shuffled in her seat and kept her eyes strictly ahead.

Perhaps she would pass his tests this way, or would at least send him a message that was clear without being too abrasive. It was what Cassie hoped, at least.

 

[Rocket1010]

Cassie rebuffs Jack's advances at the meeting

Jack chuckled when Cassie completely ignored him and turned her attention back to Robert Jackson. Jack knew the whole presentation, having read the executive summary by Robert and given to him a few days ago. Jack had read the report and made a few comments. The purpose of the meeting was to let everyone else know what marketing was doing so they could do their job. As for the notes Cassie was taking, he would review them and he was sure he could find some errors.

His fingers were sliding delicately over the swollen labia and he didn't make any attempt to push them inside. This was a test of sorts to see what kind of reaction he would get from Cassie. Would she open her thighs wider and allow him more access to her love channel? Or would she remain still and allow him to just touch her tulip lips?

A soft chuckle slipped from his lips, when he felt shift slightly, crossing her leg nearest him over the other leg. This motion denied him access to her pussy and created a blockade. 'So she wants to deny me some fun does she,' he thought, keeping his hand on her thigh.

Turning his attention to Robert's report he soon grew bored since he knew everything he was about to say. Jack looked around the table seeing the associates paying rapt attention and making notes. He chuckled when he saw some of them writing feverishly and he wondered if they actually read over their notes later or if they were trying to impress him.

As they listened to Robert drone on, he noticed that even though she crossed her legs denying him from toying with her pussy, she didn't try to knock his hand off her thigh. Jack made lazy circles with the tip of his fingers, feeling her body shifting every few minutes to reposition her legs.

Finally the report was finished and Jack moved his hand off Cassie's thigh as everyone at the table turned their attention back to him. Smiling his easy going smile, he said, "Robert .... very good report and timely I might add." Robert began passing out copies of the report to everyone. It was Jack's policy not to give the reports before the meeting to prevent employees leafing through it and not paying attention to the speaker. You all have the report in front of you along with some supplemental information to pass on to the clients. If there are no questions, we are done here."

As usual there were no questions and the employees began to file out of the room. He noticed some of them glancing in Cassie's direction as if to try and size her up. Jack ignored the looks and spoke to Cassie. "Ms. Mays please accompany me to my office." He didn't say another word and got up and walked out of the conference room expecting Cassie to follow.

When they got to his office, Jack told her to shut the door and stand in front of the desk. Jack watched as she nervously did what he asked and then stood in front of his desk. Walking up behind her, he pushed her upper body so her hands, seeing her hands land on the desk.

"Ms. Mays please keep your hands on the desk," he whispered in a more demanding tone. "You passed the test in the conference room by not drawing any attention to my actions. However it would have better served you to allow me the freedom to touch you." Jack was leaning against her back, his hand lifted the hem of her skirt and rubbed the contours of her ass.

"You must remember Ms. Mays that I am the boss and what I want I get. Spread your legs a little for me Ms. Mays." Jack's hand slid between her thighs to feel a little dampness on her the lips of her pussy. "Does this bother you when I touch you like this?" he whispered into her ear.

 

[Aluris]

Cassie forced herself to smile and nod when her boss had complimented Robert - inwardly, she still had her heart hammering away in her chest, the nerves paralysing her from doing much else. She was also... angry. Angry that he thought he could do this. This was all so vague, so confusing! Was she meant to go along with it to keep her job, or was this all some higher-up testing still?

No... no, she told herself. This was no test. He hadn't fired her after she had delivered her... underwear to him earlier. Now he was trying to fluster her in front of his entire staff. A shudder ran through her, one of her gaining an inkling of an idea.

It was as she thought this that Mr. Connor had ordered her to report to his office.
Every step there was as heavy as it was before. Cassie realised with a grimace that she was dreading it, dreading what he could ask her to do. She was desperate for this job! There was no way she could return back to her apartment and admit she had quit, right after she had told everyone... her roommate would be furious. Her parents - well. Cassie swallowed back her reluctance and opened the door to his office, head held high. She would try to explain the situation. Maybe he could simply just... hire someone else. Right?
Immediately, he took control - sitting behind his desk, he motioned her to close the door and stand before him. Despite her initial confidence just before, Cassie meekly did so, hands wringing together as she looked down at the floor. She still felt all too aware of how bare she was under her skirt. All the more so when she remembered that he was aware of it too.

When Mr. Connors stood back up, Cassie cringed and closed her eyes - she felt his firm grip on her back, pushing her forward. Without a sound she bent to support herself with her hands, forced to unravel them to do so. Her breathing became a little panicked, quicker and louder, even more so when he began to massage down... down her lower back, then around the curves of her ass.

"You must remember Ms. Mays that I am the boss and what I want I get. Spread your legs a little for me Ms. Mays.... does this bother you when I touch you like this?"

There was a slightly mocking tone to his voice, and Cassie whimpered, shoulders hunching up sharply.
"A... a little bit, s-sir." Her voice was so quiet! Inwardly she felt a rush of shame. This was not the strong confrontation she had imagined. But she felt no will to stand up and push him off, the pressure to keep her position overwhelming... "Please... I didn't know this is what you wanted. I, I don't know what to do."

Shifting her hips, she shuddered as his fingers stroked along her labia again, legs only just apart to allow him the most minimal of access. The tiniest representation of her rebellion.

 

[Rocket1010]

In Jack's office after the meeting

Leaning into Cassie's back, Jack continued to rub his fingertips over her soft pedals. He chuckled when she told him it bothered her a little bit that he was touching her personal girl part. He knew she was confused when she barely whispered that she didn't know what he wanted. This being her first day, it was natural for her to be confused by his taking advantage of her. But that was what Jack wanted for now, to have her confused to the point she would obey him without question when the time came for her to totally submit to him.

Pulling his fingers from her pussy, he smiled looking at the wetness on them. Licking them, he murmured, "Very tasty Cassie. I see you and I are going to have a lot of fun together." Grabbing her hair, he pulled her head back and his lips were at her ear. "But when I tell you to spread your legs for me I don't mean just a little."

Letting her hair free from his grasp, he pulled her skirt over her hips and quickly swatted her ass with a loud SLAP! "I think I have your attention now Cassie," he whispered in a hushed rough tone. Delivering another ..... SLAP .... SLAP ..... he could feel the sting in his hand. Rubbing her warm ass cheeks, he leaned over her again. "Now do as I say ...... spread your thighs for me."

Shoving his hand between her thighs he felt them squeeze against his intruding fingers. He pushed them further feeling the softness of her pedals, one finger pushing delicately at the folds waiting for her to obey his command.