Executive Sexual Assistant

[GuyRP]

"Miss, you need to sign this non-disclosure form." A pleasant young woman, about your age was handing you a clipboard. She was a secretary at the company and had been your guide during one of your three previous interviews. This time, however, you were hear alone. At the first interview there had been many candidates. Less at the second. A handful at the third.

"Normally we don't do non-disclosures for interviews, but Mr. Wright is far from normal. He's the only executive without a personal secretary or an assistant, though apparently the board insisted he take on an assistant. Which is what you've been interviewing for. I don't know why he insisted on the non-disclosure. Maybe he wants to go over some real life scenarios with you, get your take on them."

She took the clipboard from you and motioned to a door down the hall. "Mr. Wright will see you now."



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OOC:

You are a recent college graduate. You have a great deal of debt. You need a job. The only places hiring is retail and fast food. You're applying everywhere. You put in for an assistant position at a multinational. You're not sure what the job entails exactly, but the money's good. After three rounds of interviews you're about to interview with Mr. Wright, the man you'll be assisting.

During the interview I make it explicitly clear that as part of your job, the main part of your job, is as my personal sex worker. You will end your other relationships and be exclusively mine for the duration of your time in this position. You notice there is no provivion in the contract for me to be exclusively yours. Set it in a state where prostitution is legal, Nevada or Rhode Island. You have to sign a non-disclosure before we discuss the final details. You will be gaining valuable job experience.

Please take a look over my other threads to get a feel for my style. Pm if interested.

 

[sierrahughes]

I noticed how there was a distinct change in the interior design as I approached Mr. Wright's office. From a clean, corporate look to one with subtly darker tones. I knocked on the door and waited. A few moments later, enough to make me anxious, a deep voice told me to enter.

I stepped into a bright spot, something of a foyer area in an incredibly large office. There was a man behind the desk but he was barely visible with no lights above him. I made a move to take a step towards the desk but the man told me to stop.

"Turn around," he added.

I tentatively took a few small steps to turn my back towards the desk, almost feeling his eyes looking me over. It reminded me of something. In the three rounds of interviews, I had noticed a few details. I wasn't absolutely sure, but I was going to hypothesise that there were some common physical traits of the women who made it through the interviews.

In the third round, I was the only brunette.

In the second round, only the women with some curves made it through.

And in the first round...well I hadn't figured that one out yet. Of course, it was pure speculation. This was the year 2015 - do people still hire based on physical traits? Besides, I was one of three well-endowed brunettes so this interview process could have been made a lot shorter, unless...

"Turn around again," his deep voice interrupted my thoughts.

I turned once more, this time with a bit more grace than the first time. I was wearing a white blouse that seemed a little tight - it was my only white blouse from the time when I had this etiquette class in college. This was matched with grey pants that was held up nicely by my pert ass.

I stood there for a few more moments, feeling more scrutinised than I have ever been.

 

[GuyRP]

Warren looked the girl up and down. She was very attractive, with curves in the right places. A pert ass and those tits! Yes, they were quite nice. Even though the shirt was tight, and they were at eye level, he could not tell if she was wearing a bra.

The lighting was working against him. The shades were drawn, and the lamps were aimed away from him, toward the applicants. This obscured his face and gave him an excellent view of the girls. It did let her see his arms and chest. His shirt was loose, but betrayed no hint of flab or fat. In fact, he was in excellent shape. It was too dark to see them, but there was a stationary recumbent bike in the corner next to a multi exercise piece of gym equipment.

Warren shook his head as he remembered how he came up with this scheme, the hours spent pouring over laws. The board had insisted he finally hire an assistant. He didn't need or want an assistant. It was while reading an article about the Bunny Ranch near Vegas that the idea formed. Prostitution was legal in this state too. There were restrictions, of course, but he now knew them by heart. He was legally clear.

Of course, he's never done anything like this before so he was trepidatious. Warren knew he could not let that show. He had to be the epitome of confidence. His deep bass voice helped in that regard.

"You chose your outfit well, Miss, though it is more conservative than I like. Sit down."

As she complied he shuffled through the personnel files, looking for her picture, so he could find her name.

"Tell me about yourself," he commanded as he looked for her file, "Be prepared to answer very intimate and personal questions. If you get this position you will be working very closely with me. I will not be blindsided by something I forgot to ask before I hired you. You understand."

 

[sierrahughes]

Sierra's lips parted slightly, but she paused.

She had been through this over and over again before this interview - how to introduce herself. But yet she found apprehension building within. And her throat dried up momentarily.

"...it is more conservative than I like..."

Taking in a soft breath, sitting up straight by pulling back her shoulders, she reminded herself that she wanted this job. Retail and fast food were decent jobs, but not what she had envisaged as her future when she went to college.

"Be prepared to answer very intimate and personal questions. If you get this position you will be working very closely with me. I will not be blindsided by something I forgot to ask before I hired you. You understand."

"Of course, Mr. Wright," was Sierra's first response, even though she had little idea what was to come next. She looked up into his eyes, hardly moving her gaze as she wanted to come across as being able to hold her own in an interview. She had heard from the secretary handling the interviews that Mr. Wright was not a common man.

"I'm Sierra," Sierra's eyes drifted momentarily to his upper body. He looked toned, but not too muscular. It was exactly her type.

"And I had a perfect score for my SATs. I went to a college in Nevada instead of Berkeley or even Stanford because my family could not afford it. I am telling you this because I want you to know that I am capable, a fast learner, highly motivated and will not let you regret hiring me for a single moment."

Sierra realised she forgot to breathe. And then she paused, her heart racing.

 

[GuyRP]

When she sat up and pushed her shoulders back Sierra was effectively pushing her breasts out to press against her tight blouse. It was a pleasant show and Warren began to feel his loins begin to stir.

He looked at her skeptically at her SAT and college comments. "If we met in the gym or at a singles bar, is that what you'd lead off with? I have your resume right here."

Warren waved the file and dropped it on his desk. "Congratulations, you're just as qualified as half a dozen other people. That's why you are here. If you're going to be working under me you must be compatible. What kind of movies do you like? Do you read? What excites you, turns you on? What are your dreams? Hopes? Personal things like what you do on the weekends, are you a virgin, when did you sneak your first drink? Hell, telling me an embarrassing story would be better than telling me something I already know."

Warren watched her reactions. He wanted to see how she handled the sexual questions tossed in casually with the nonsexual ones.

"So unbutton your blouse a bit and relax. You're either the person I want, or you're not."

He paused, giving her a moment to let that sink in.

"Now, start again, tell me about yourself."

 

[sierrahughes]

"If we met in the gym or at a singles bar, is that what you'd lead off with? I have your resume right here."

Sierra had to restrain herself. The first rule of any interview - don't get defensive. But before she knew, she was caught off-guard by a barrage of questions. What should she begin by answering?

"So unbutton your blouse a bit and relax. You're either the person I want, or you're not."

And then this. This was completely unexpected. Was this the line where she would have to determine whether she was being sexually harassed by the gentleman who could be her future boss? Or was it just another way for him to test how she would respond under pressure?

Whatever it is, Sierra had to respond. And fast.

She reached up to the top button of her blouse, her fingers lingered momentarily before she undid not one, but two of her buttons, her full breasts threatening to spill out a little as she unveils her black-laced bra underneath.

"These are real, as is everything else. When it comes to me, what you see is what you get," Sierra paused once more, catching her breath. She wasn't thinking now - just responding by instinct.

 

[GuyRP]

Damn. That answered the bra question. They were very impressive breasts and He could feel his body responding to her. This was promising. Warren didn't miss a beat in complimenting her.

"Excellent. You're obviously very proud of your breasts, and rightly so, they look quite," he paused, letting the moment draw out, "enticing. Tell me more. Are you proud of the rest of your body? Is there another part of your body that you enjoy as much as your breasts? Do you maintain your physical assets with exercise? Yoga perhaps, or Pilates?"

This interview was progressing well. Two of the previous applicants had glossed over his less sexual questions, so he hadn't proceeded to the risque with them. Sierra seemed eager to talk about them, diving in with her sexuality out front.

Would he have her naked soon? Kneeling before him to worship his cock? Perhaps. He still hadn't told her what the job actually entailed.

 

[sierrahughes]

Sierra was learning quickly. This wasn't a usual interview, and Mr. Wright wasn't a usual boss. And clearly, Mr. Wright was more interested about her sexual preferences, more so than what she did to keep her physical shape.

Well, Sierra might have chosen to talk about her days playing as forward in the her college women's soccer team. Or how she made it to the All-American team one year.

"There is," Sierra paused long enough to turn her head slightly to the side, as she raised her finger to a spot behind her ear facing Mr. Wright.

"...this spot right here. When you kiss it right, it sends all kinds of tingles down my spine," Sierra held her finger there momentarily, before turning to face Mr. Wright again.

She was starting to become intrigued. What does he want from her exactly?

 

[GuyRP]

Warren didn't stare, but he didn't look away either. Sierra was a very attractive woman, and the nape of her neck was pleasant to look at. Especially when she was telling him how to sexually stimulate her. Warren decided to step up the questions. She seemed to be what he was looking for in an assistant.

Emphasis on the ass.

The bad joke was in his head but Warren still chuckled aloud and then said, "Very well, I'll have to remember that. Since you seem to be interested in sexuality we may as well get those intimate questions out of the way. Tell me about your sexual history Sierra. Are you a virgin? What is your favorite sexual activity, or if you are a virgin, what do you fantasize would be your favorite sexual activity?"

 

[sierrahughes]

"My favourite sexual activity..." Sierra pondered aloud. She wasn't sure why Mr. Wright was asking these questions, or what he meant exactly.

She was no virgin, that was for sure. She was one of the popular girls throughout her school days; not that it made her a mean bitch, but she had a fair share of heart-breaking (sometimes her own) over the years. And as cliche as it was, she lost her virginity one night in the back of a car.

"I'm not quite sure what you mean, Mr. Wright," Sierra asked. She had some thoughts come to mind of course, so it wasn't as if she really needed to make this clarification. But since an interview works both ways, she wanted to make Mr. Wright uncomfortable too.

Another thought did pop into her mind. She could be considered a virgin, in a way. She has never let anyone fuck her in her ass.

 

[GuyRP]

Warren leaned back in his chair and out of the light. He watched Sierra's physical reactions when he let her comment hang there for a long moment as he gathered his thoughts. Let her stew in the silence. He didn't like the back talk, but how to squash it appropriately? On the other hand, she was teasing him, and that was a good sign. After the minute hand on the clock ticked forward a notch, he leaned forward and gave her a smile that was quite predatory and not at all reassuring.

"It was a straightforward question Sierra, but if you want clarification, well, let me clarify. I am interviewing you for a job with an annual salary equivalent to the cost of a new Porsche. If you want the job, you will answer my questions." Warren's voice didn't get louder, rather the opposite. He got quieter, and spoke slower so his listener had to pay more attention.

"So here is the question, Sierra: what do you enjoy doing when you fuck?"

 

[sierrahughes]

Sierra's eyes lit up. Not because of the mention of her salary, even if that was the first time she received any indication of her actual salary. Throughout the interview process, it was only alluded that the salary would be "very competitive".

Sierra's eyes lit up because she sensed a distinct change in his tone and approach. He was cutting away his bullshit and getting straight to it. She was certain that her ridiculously high salary offer was not simply based on her telling her future boss about her sexual preferences and activities.

And yet, she resisted taking the bait. What bait? Sierra was sure that inside Mr. Wright's deepest and darkest fantasies, his future employee would stand up, walk over to his seat, and showed him exactly what her favourite sexual activity is.

Sierra took in a deep breath, and then sat back into her armchair, crossing her arms below her full chest to push her breasts up deliberately, as she made a slow move to cross her legs. Too bad she was wearing her pants.

"For one, I love the foreplay. The greater the anticipation, the greater the satisfaction," Sierra replied softly too, matching his volume. She smiled, licking her lips a little in anticipation of what might come next.

 

[GuyRP]

Sierra took a deep breath, causing her large breasts to rise up, and then crossed her arms under them. With her mildly unbuttoned blouse she was clearly putting her breasts on display for him. Warren felt his arousal grow. Then she crossed her legs in a slow move that was clear out of Basic Instinct. If she was old enough to have seen that movie.

Warren liked her answer, but either she really only liked foreplay, which was doubtful, or she was playing the waiting game too, drawing out her answers. She liked anticipation, it was probably the latter.

"Go on Sierra. Unless foreplay is all there is. That would be... disappointing."

 

[sierrahughes]

"Should I...continue with the foreplay?" Sierra asked, raising one arm to pull her hair back, away from her eyes and behind her ears, her fingers lingering on her ear, and then to the side and nape of her neck. She took in another sharp breath, thrusting her breasts out once more, still pushed up by her other arm that was across her chest.

"What exactly would be my job role," Sierra asked, and then paused.

 

[GuyRP]

Warren smiled. The million dollar question. He considered being vague, but didn't see the point. From the way she was displaying herself there was a fairly good chance she would be interested. And if not, he had the non-disclosure, so he could sue if she went public.

Warren took a deep breath and looked Sierra over again. Yes, she would do quite nicely, if she was willing.

"As you may or may not know, the board of this company has decided in their finite wisdom, that after five years of exemplary service I need an executive assistant. Quite frankly, I do not need one. After contemplating the requirements of the position and the laws of this state I have decided to hire someone to provide a service I would enjoy."

Warren stood. He walked around the desk and stepped over Sierra's legs and turned to lean against the desk. Now he had one foot on either side of her chair, his legs spread and his crotch directly in her line of sight.

"Prostitution is legal in this state. That is a well settled bit of law. So I decided to hire an Executive Sexual Assistant. I am hiring you to be my personal sex worker, prostitute, whore, fuck toy, cum slut, call it whatever you like. If I hire you then you will please me whenever, wherever and however I ask. You will give up all other sexual relationships for the duration of your employment. You will maintain the fiction that you are a normal Executive Assistant, and if you pay attention you may even learn a thing or two that you can use when you decide to move on."

He stopped, staring at her breasts. "Do you have any questions, or shall we continue with the interview? I will require a demonstration of your skills."

 

[sierrahughes]

Well, college didn't exactly have a class on How to Fuck Your Way Up the Corporate Ladder. Not officially anyway.

But Sierra had plenty of training. And she knew that one day, she might have to turn to this. She just hadn't expected that day to come so soon. For her first full job, no less. Not to mention that she had to seek employment in that one state where prostitution was actually legal.

Sierra listened carefully, and also watched how Mr. Wright began to position himself, unambiguously standing before her. He had made his offer, both verbally and non-verbally. And now she needed to give him an answer.

She thought for no more than a moment, before reaching forward, for his zipper. The sound of the zipper parting ways seemed amplified for some reason, breaking into the deafening silence of the room. If she came across as hesitant, he would be wrong. Sierra was, in fact, terribly excited.

The zipper soon reached the base of the opening, popping slightly open as she could make out the outline of what must be Mr. Wright's cock, throbbing a little with each passing moment.

As she reached inside that opening, she looked up at Mr. Wright at the same time, her eyes gazing deep into his. She could tell that this seemed to be a moment he had been anticipating, and his eyes gave away a copious amount of lust. She could only imagine what else he had in store for her.

But first, she was going to start with something quite basic, yet fundamental. Her fingers quickly found his warm cock, wrapping gently yet firmly around it. She gasped a little when she realised that she could barely cover the entire girth of his cock.

With a little tugging, she managed to direct the head of his cock out the opening, his manhood now hanging gloriously between them. She gasped again - it looked even larger than she had thought, and he was probably still filling it in with each passing moment of thinking what might come next.

Her head leaned forward this time, breaking the gaze into his eyes momentarily. She pursed her lips, letting a string of her saliva fall just nicely on the head of his cock. She brushed her hair back behind both her ears, looked back up into his eyes, before wrapping her fingers back around his cock as she began to lube it up with her spit.

"If you like what I'm about to do next, I do have some conditions for you to consider," Sierra paused even as she slowly stroked his cock, only long enough for him to want to fashion a response as he parted his lips, as if beginning to speak.

But Sierra didn't let him, as she descended onto his now bulging, purple head, and wrapped her lips around it in a tight suction.

"Mmmmm..." she hummed on it as she flicked her tongue out, tasting a little bit of his pre-cum.

 

[GuyRP]

She was eager, Warren had to give her that. It was a long speech for him, but Sierra didn't hesitate. She went straight for his zipper and dug her hands into his pants to work out his cock.

It was only half hard, but still quite large. He put his hands behind him on the desk and let the Young lady go to work. Pleasure radiated through his body as she began to stroke him. She seemed to know what she was doing, lubricating his cock with saliva and rubbing it up and down his shaft.

He could see the Lust in her eyes, and the excitement inn her smile. Fuck. She wanted this as much as he did. Maybe more. Had he finally found the right girl?

"If you like what I'm about to do next, I do have some conditions for you to consider.". Conditions? He was the employer here. He set the conditions. What did she have in mind?

He opened his mouth to ask and she opened her mouth and put it to a much better use. She moaned around his cockhead and Warren closed his eyes and leaned back, letting the sensations wash over him. Sierra knew how to use her mouth, earning a jump from his cock, the head pressing up against the roof of her mouth when her tongue clicked the underside of his cockhead.

He put his hand on her head, caressing her gently as she worked. He was tempted to hold her in place and facefuck her, but he wanted to see what she could do first.

"Fair enough. I'd like to hear your conditions. After you show me you can get me off."

 

[sierrahughes]

His leaning back, the jump of his cock, his hand on the side of her head - all signs that he liked what she was doing. And she had barely started! And of course, when he started his negotiation about discussing conditions only after she got him off, Sierra smiled, and got to work.

Reaching up to the base of his cock, Sierra caressed his balls as gently as she nursed the tip of his cock. She stared back up into his eyes, and then let his cock fall out from between her lips, leaving nothing more than a trail of saliva connecting his now glistening cockhead and the side of her mouth.

"Would you like me to..." Sierra leaned forward, her nose now next to his pelvis, the base of his cock. Without asking further, she craned her neck a little, and flicked her tongue out to drag it across one side of his ball sac.

And then in the next motion, she pulled his cock aside with her other free hand, and then took one entire ball into her mouth. And she sucked hard, with lewd smacking sounds now filling the vast office.

She looked up again, to see if he liked what she was doing.

 

[GuyRP]

Warren watched Sierra work his cockhead, enjoying the pleasure it was giving him. Sierra was proving herself to be quite experienced in the oral arts, focusing on his cockhead.

Before she could pull a moan out of him, Sierra's lips released him and her hand encircled the base of his cock, putting herself in a position to move it. She started to ask what he wanted and then leaned in and licked his heavy, hairy ball sack. She shifted his cock a bit to one side and began taking aa testicle into her mouth. Warren let out a moan as she sucked and slurped on his balls.

"Good girl. Yes, that feels good, but it's your audition for cumslut. If you want to be my fuck toy, show me what you've got. You need to earn the right to be my whore, prove yourself worthy to be covered in my cum and marked as mine."

That was more than he had intended to say, and certainly one of the dirtiest things he had ever said. But, well, fuck, if she didn't like it, well, she didn't have to have the job.

 

[sierrahughes]

Sierra got more than what she could hope for. Not only did he let out a deep moan in response to her. He began to talk dirty. It was the surest sign that she was getting him going. It was also a prelude for what may come - a successful employment stint. Sierra could not wait to start her job.

She stopped sucking on Mr. Wright's balls, and began to slowly stroke his still hardening cock. She paused, and then licked her lips. And then waited, as she looked up into his eyes. She wanted him to hang on her every next move. To anticipate what was to come. To have that unbearable urge to want to come and yet want this moment to last forever.

Still with one hand wrapped around his cock, moving back and forth, Sierra slowly stood up. Even on her heels, she still found herself looking up at the towering stature of Mr. Wright. She smiled, loving this moment herself. She wanted him to know that she was his. That this job was hers. And that she would be about to give him an amazing time.

Then she descended, her eyes never once leaving his, onto her knees. The flooring, as she had noted earlier, was carpeted. She made a mental note, of not letting even a single drop of cum stain it when it eventually comes.

With the wad of saliva that she had gathered in her mouth, she positions the length of his cock just below her lips, as she proceeded to let the liquid drizzle over it like sauce over a sausage. She gave his cock another stroke, this time the lubricant helping to create the unmistakable sound of the stroking of cock.

She pulled his cock to the side of her face, as if comparing the length and girth to the size of her face.

"Has any whore ever managed to take in your big, fat, cock? Do you want your cumslut to slide your big, fat cock into her lips? Do you want your cumslut to take all of it inside? To choke on your cock?" Sierra began, slowing down her strokes even more as she now rubbed the length of his cock along the side of her face.

She parted her lips and enveloped the tip of his cock head. It was larger than the last time when she sucked on it. And she relished this new challenge.

With a single motion, she descended her head down the entire length of his cock, and let his cockhead nestle against the back of her throat.