The Boss And His Personal Assistant (reserved)

[JS1979]

Jenny still lives with her mother at the age of 29. She's been working at odd jobs here and there . Recently found herself lucky to see another opportunity:

Help wanted. Personal assistant
Job description:
1. Booking and arranging small luncheons, light entertainment and occasional travel,
2. Maintaining the home and personal life of the employer
No formal academic qualifications or experience are required
Emailto: MrSTheBoss@XYZ with at least one photo

The ad doesn't say if it's a business or what. Must be hiring a private assistant for a rich man or something. This is the type of work Jenny has in her day-dreams ever since she dropped out from her first year of city college. Jenny was happy to send out her resume.

.............. I do have experience as a private personal assistant for a business man. He said I was good. I currently have a weekend job at a club and available for another one Monday through Friday..........This is a photo of me...........welcome to ask me any questions.


A few days later, she received a response email asking her to go for an interview. She took a deep breath and gave herself a pat on her chest.

Following the instruction to the coffee shop for the interview, she walks into the door, feeling proud. There...there's a man in an expensive looking blue suit as described in the email and .....oh,....a woman is with him looking rather sharp.

“Hi, are you Mr. S ? I am Jenny.”

(OOC: this thread is reserved for Mr.S. Nobody else should post)

 

[staylate]

"Hello, Jenny." The woman stands up and shakes your hand firmly. "Please, have a seat." I nod my head but don't make any attempt to shake your hand. I casually look you up and down, but otherwise remain stoic.

"Jenny, we have a unique opportunity for someone such as yourself. Mr. S. is a busy and quite successful entrepreneur and venture capitalist. He needs a woman he can count on to keep his schedule, and make sure his home and office are always available and appropriate for meeting investors and clients. This means you will need to spend a considerable amount of your time at both his home and his office. You'll keep his appointments, make his travel arrangements on his private jet, and ensure that he has everything he needs to be successful. In return, you'll be very well compensated, and there are many ...benefits. Does this sound like something you're interested in?"

We both wait for your response. We've had three interviews before yours and none of the candidates showed much promise. But I can tell that you might have an edge that I will appreciate.

 

[JS1979]

The woman who is doing most of the talking must be joined at the hip with Mr. S. A VIP! And he referred to her as "the woman" ? There must be a story behind the scene.

So, the man is a capitalist....a capitalist needs me to make sure that he has everything he needs to be successful....hmmmmm. I told him in my resume I dropped out from my first year of city college. I know a capitalist means he is not a communist and most of them are rich. I have a tender soft spot in the bottom of my heart for rich men. This guy right here looks like one.

I can see he is sizing me up, staring and evaluating while letting the woman do all the talking. But I wonder why he said to me “I casually look you up and down”. Odd. Questionable. Does he think I am visually impaired, blind or what? The clients at the swingers' club I work at don't talk to me like that. They just do it.

Well, I don't want to argue with this guy here now. It would be foolish of me to do that before I get this job.

“Oh, yes, Mr. S. And Ms......sounds good. “

 

[staylate]

[Lol, I didn't say "I casually looked you up and down." I just did it-all I've said so far is "Hello Jenny" and "please have a seat."]

"Jones." She answers your question about her name. "Mr. S. runs a rather large investment firm. He has many clients all over the world. We know from your resume that you don't have a college degree, but Mr. S sees something in your background and Mr. S reads people for a living. I've never seen him be wrong when it comes to choosing those around him."

"Jenny," I interject, "tell us a little bit about your work experience. And also, tell us what you're hoping to accomplish should I decide to hire you." I lean back and await a response, but my eyes wander from yours down your body, and back up again. You're stunning and your dress is exactly what I was hoping you'd wear. I can tell your confident and world-savvy and street-smart and those are just the qualities I'm looking for.

 

[JS1979]

"I've been working part-time...i can do some simple typing... before my current weekend job at the club I worked for a wealthy man at his large house, also as a personal assistant. Duties were similar to what Ms. Jones just described....Oh, I forgot to say that I've been going with my mother to her employer's house once a week and we usually stay overnight....It's not a paying job. I can get away sometimes but just to let you know. You can count on me 4 days a week for sure. 24 hrs each.”

 

[staylate]

"There will be some late nights and plenty of overnight travel. But it sounds like you'll be available for that. I think the next thing to do is go show you where you'll be doing most of your work." I explain. Ms. Jones looks over at me and asks "will you be needing me anymore today, then?" "No, you can head back to the office. I'll take it from here, assuming Jenny is still interested," I answer.

I don't really wait for your response, I gather up my keys and stand up. I go over to your chair and pull the back out for you as you stand up. "Jenny, would you prefer to ride up to the house with me, or would you prefer to take an Uber, that we'll pay for of course?" I ask, fairly certain of the answer, but wanting to give you your space.

 

[JS1979]

Mr.S is taking Jenny to his house. She can be sure she's got the job now.
"There will be some late nights and plenty of overnight travel."
and she can be further assured that there will be sex involved in this job. She actually could smell it the minute she saw Mr. S with sexy Ms. Jones together.

Jenny is releasing a stream of positive energy onto her face. Her eyes are twinkling. Standing up from her seat her bosom goes straight forward. This is it. Mr. S didn't say anything about office work. Jenny is not looking for office work. She is looking to be a business man's PERSONAL assistant. And ah....yes....overnight travel.....staying at different hotels.....she would walk into a hotel entrance swaying her hips and shaking her tits..

“ Mr. S, I'll ride with you in your car to your house.”

 

[staylate]

Mr. S notices a change in Jenny. She instantly exudes confidence, one of his biggest turn-ons. He knows he doesn't need to tell her she has the job, and he also knew she wouldn't be riding to his house in an Uber.

Ms. Jones gets up shakes your hand and smiles her goodbye. I put my hand on the small of your back and guide you out the door like a gentleman. As I do, my pinky finger softly brushes against the top of your perfect ass. I walk down the block for a minute and then stop at a shiny black Alpha Romeo SUV. I go to the passenger's side and open the door for you. The inside is black leather with red trim, and the vehicle is immaculate. The windows are tinted making it almost impossible for anyone to see in.

I get into the driver's seat and push a button to start the car. We pull out into traffic. We head out onto a road that leads onto hill that overlooks the city. The mansion sits atop a hill and the walls are mostly windows. The sun is setting over the ocean behind us.

"Well, shall I show you around? You'll have an office here, your own bedroom that you can use anytime you like. There's a large pool out back that you can use during your free time. What would you like to see first?"

 

[JS1979]

This is it. This is Jenny's style. A mansion. She's been to several nice houses but may not be a mansion. The current big house she's been going with her mother once a week belongs to mother's employer, Bob, at his massage parlor.

Mr.S has a mansion! At the top of a hill overlooking the ocean!! As Jenny followed him through the front entrance to the living room, Jenny, again, has her bosom straight up and forward. Her breasts bounced in response to the sight before her eyes. This is ideal for private house parties, better than Bob's. Jenny is good at house parties where she is capable of doing what needs to be done.

So, Mr.S' mansion does look very nice . After a few minutes of euphoric thrill Jenny suddenly realized she hasn't seen anybody else around in this big house. Not even a house-keeper? If Mr. S is hiring her to be a house-keeper, she'd run in a high speed. She is not that type. She is better at flirting with men in lingerie than doing house work.

"Mr. S, ......very nice.............It's...... so quiet......Not even a cat ? Nobody else around? Are you the only one living here?"

 

[staylate]

"I'm allergic to cats," I say, looking at my phone. I put it down and look at the Rolex Submariner on my wrist. "Oh, you know what, the staff will be here in just a few minutes. I have several people who work here at the house for me. Often times my accountant is here. And you'll meet Rose, my housekeeper. She's the one who really keeps the place sparkling. She doesn't live here, though. She lives closer to town with her grandkids."

I look you up and down and again, this is the first time I've gotten a good chance to see you standing instead of sitting and I know I made the right choice. Everyone is going to be mesmerized by you.

"Jenny," I say, interrupting my own thoughts, "I'm having a party tonight. It's not very big, but some very important people are going to be here. I know it's not much time for you to prepare, but I'm going to need you to be available. Will that be an issue?" I ask, pretty sure I know the answer. "And you'll need something, exciting, to wear. In my office there is my computer. The password is 12354, not very cryptic, I know, but you'll have access to that computer at all times. Anyway, go online and find something you want to wear tonight. It needs to be something that will grab people's attention, but not be too distracting. Do you understand? Once you find what you like, order it. The credit card is stored on the computer. I'll have Edward, he's my chauffeur go and get it from whatever store you purchased it from, just be sure it's from a store here in town. Before you do all that, though, would you like me to show you to your wing of the house?"

 

[JS1979]

A party tonight!
"I will remember your password,12345, and after you show me the entire house I will go online to find something to wear tonight....The house-keeper doesn't live here? If you want me to hang around in the evening or even overnight, I can do that. I think I've let you know you can count on me minimum 4 days a week. 24 hrs each. Or even 5 days a week.”

The more I look at this living room the better it looks for me to lounge around and enjoy the large flower garden surrounding the house. I will wear something casual, something loose and comfortable. I will stand by the window so that the gardener or the chauffeur can see me. They'll learn whatever I am going to wear tonight would cost more than their monthly pay..They'll also learn that Mr.S just gave me permission to use his credit card.

“ I'd try my best to learn whatever you need me to do for you, Mr.S”

And I'd even go outside to the garden to pick some fresh flowers and put them in the vase for every room, especially for Mr.S' bedroom when he has a lady friend or me for a good time.....Ah...........very nice.

“ Very nice, Mr. S.”
As I am putting all those pictures into my head, Mr. S. Is taking the lead to show me another room.

“ It's only 2 o'clock now. We should have plenty of time before the party tonight.”

 

[staylate]

"We have plenty of time. And the staff won't be around until a bit later, and when they come in they'll be in other areas of the house."

I take you to a separate wing of the house. It has a large bedroom with an adjacent bathroom complete with soaking tub and shower. The window over the tub looks out onto the pool and to the ocean beyond. There's a walk-in closet with a jewelry box on the set of drawers in the middle of the closet. "Pick out something you want to wear tonight." I say, pointing to the jewelry box. I also have something nice you'll want to wear under the dress you buy for tonight's party. I go over to a shopping bag and pull out a box. The box is from Hermes. Inside there is a piece of very sexy lingerie.

"I'd like for you to wear this tonight." I say, though it doesn't sound like a request, but not exactly like an order. The lingerie is black and lacy and leaves little to the imagination. I hand it to you. My cock starts to get hard just thinking about you wearing it. "There are several pairs of high heels in the boxes over there," I motion to another corner. "You can wear those, or buy yourself another pair, if you like."

"You're going to be part of the...entertainment...tonight, to a certain extent. Is that alright with you?" I ask, leaning against the wall of the large closet. The house is quiet and the bed is made and very large. "This will be your space, when you're here." I explain.

 

[JS1979]

"The bed is very large. This will be your space when you're here."



Jenny is suddenly feeling a whirl of feverish heat sweeping across and throughout. Frantic. Getting frantic. She supports her mother's idea that luxury is the best aphrodisiac. Of course, Jenny will be happy to be part of the...entertainment...tonight. She will be more than happy to get fucked tonight. Mr. S said “ some very important people are going to be here.” Jenny will be ready...in this bed...in the living room....and in Mr.S' bedroom....
“Oh, you mean this is my room?....where's yours?”
Jenny can see Mr. S' cock is growing big inside his trousers. She can feel her pussy muscles tingling, sensations of tiny little pins prickling.......A box of jewelry and lingerie in this room...There's an image popping up onto her head. It's an image of Mr. S fucking a woman who was wearing that piece of lingerie and jewelry in this bed. Wondering how he is going to fuck her tonight, Jenny sways her hips as she takes a step following Mr. S to another room.

“where's your room ? where's your computer?”​

 

[staylate]

"The bed is very large. This will be your space when you're here."

View attachment 2382391

Jenny is suddenly feeling a whirl of feverish heat sweeping across and throughout. Frantic. Getting frantic. She supports her mother's idea that luxury is the best aphrodisiac. Of course, Jenny will be happy to be part of the...entertainment...tonight. She will be more than happy to get fucked tonight. Mr. S said “ some very important people are going to be here.” Jenny will be ready...in this bed...in the living room....and in Mr.S' bedroom....
“Oh, you mean this is my room?....where's yours?”
Jenny can see Mr. S' cock is growing big inside his trousers. She can feel her pussy muscles tingling, sensations of tiny little pins prickling.......A box of jewelry and lingerie in this room...There's an image popping up onto her head. It's an image of Mr. S fucking a woman who was wearing that piece of lingerie and jewelry in this bed. Wondering how he is going to fuck her tonight, Jenny sways her hips as she takes a step following Mr. S to another room.

“where's your room ? where's your computer?”​

"My room and computer can wait. It's time to educate you on your role here." I say as I walk towards you. I put my left hand firmly on your ass and squeeze. My cock is now at full staff and presses against your belly just above your pussy. "You see, Jenny, my investors are men who have great needs. And they are used to getting what they want. I'm no different." I start to massage your ass as my other hand cups your breast and squeezes your nipple over your dress. "So, when my colleagues or I decide we want something, we tend to just take it. And I want someone who wants to give as much as we want to take. I know you understand." I pull up your dress and rub my hand on your ass cheek. It's firm and perfectly formed. I feel your nipple grow hard under my hand. I can feel your breath on my neck.

 

[JS1979]

As they stepped out the room, into the hallway, Mr.S suddenly stopped and pressing his cock against Jenny, pulling up her dress and rubbing her ass. She has crotchless panties on. She came to this job interview today carrying a fantasy in her mind and came on crotchless in case the prospective employer wanted to fuck her pussy. She would let men fuck her if they have a good potential. Mr. S is one of them. He even has investors as his clients...coming to the party tonight....

The fantasy she had today is coming true right now. Jenny's pussy is tingling and swelling just like a slut. Mr S is pressing her against the wall in the hallway. Lifting up one of her legs, her plump pussy is exposed. She was once in this position with a man in the dark alley behind the club at the midnight hour.

Mr.S is pulling out his cock.....

 

[staylate]

As they stepped out the room, into the hallway, Mr.S suddenly stopped and pressing his cock against Jenny, pulling up her dress and rubbing her ass. She has crotchless panties on. She came to this job interview today carrying a fantasy in her mind and came on crotchless in case the prospective employer wanted to fuck her pussy. She would let men fuck her if they have a good potential. Mr. S is one of them. He even has investors as his clients...coming to the party tonight....

The fantasy she had today is coming true right now. Jenny's pussy is tingling and swelling just like a slut. Mr S is pressing her against the wall in the hallway. Lifting up one of her legs, her plump pussy is exposed. She was once in this position with a man in the dark alley behind the club at the midnight hour.

Mr.S is pulling out his cock.....

He grabs his hard throbbing cock by the base and eases it into Jenny's warm soft pussy without saying a word. He presses her hard against the wall as he fills her up. His other hand takes her ass and squeezes it. "I knew you'd be ready for me." He says in an ecstacy-filled growl. He begins to thrust up and in, lifting Jenny off her feet with each thrust. "Fuck, your pussy is even tighter than I imagined it would be!"

 

[JS1979]

The quick fuck in the hallway was just a foreplay for the evening to come.
Mr S showed me another room that's to be my office and the computer is right here. He's walking out and I'm staying to get online to order what I need for the party tonight.

Jenny is ordering this dress. Ever since she turned 18, her mother has been telling her " when I take you with me to meet my man, always wear something low-cut in front, something easy for the man to pull out your breasts to play with."


In addition to the lacy black lingerie Mr. S showed her, Jenny is ordering another one:

This piece is for the time after everybody has some drinks and loosening up. She'll change into this piece after a shower .

“And, in addition, the shoes....right here....”

The chauffeur is already waiting by the computer waiting for Jenny to tell him where to pick up those items. " Here's the address of the store. By the time you get there, everything should be ready for pickup”

 

[staylate]

He leaves and heads to the stores to pick up the items. He had a chance to peek at what she was getting. "She's got great taste," he thinks to himself.
Mr. S, meanwhile, receives messages on his phone from the stores with pictures of the items purchased. He knows that she's going to look stunning. The staff returns to the house and begins to go about their duties. One of them, Richard, is Mr. S's accountant. He's aware that Jenny has been hired, but does not know that she is in the house. He is used to walking around like he owns the place, and he walks into Jenny's room. "Oh! I'm sorry, I didn't realize anyone was in here. You must be Jenny. I'm Richard, you can call me Rich." He walks over and politely offers a handshake. "Has Mr. S been treating you properly so far, Jenny?"

 

[JS1979]

The chauffeur took off to pick up the items. As I am turning off the computer there's a man standing by the door, "Oh! I'm sorry, I didn't realize anyone was in here. You must be Jenny. I'm Richard...”
“ Hi, yes, I am Jenny.”
"Has Mr. S been treating you properly so far, Jenny?"

This man must be very buddy-buddy with Mr. S to be talking like this. There must be quite a lot for me to learn in this house.

“OH, Mr. S is very nice.” I'm walking out to the hallway, “Where is he? I thought he was going to show me the rest of the house.”

I now hear noises and voices. Must be the staff. I Wonder why the staff comes at the time approaching late afternoon. Must be preparing for the party. A middle aged woman is already in an apron, carrying something, probably a cook. Oh, I have to call my mother.

“Mom, I've found a job.....doing an interview now.......I don't know if I'll be home tonight.....he seems OK.....I'll tell you everything when I get home tomorrow.”

I see they are setting up the dinner table. It looks big enough for at least 10 people. Imagine I'll be wearing the red dress I just ordered, sitting next to Mr. S, smiling at all his VIP clients...imagine.....

 

[staylate]

"Oh, Jenny, let me show you today's colors and where you'll be seated." The middle aged lady takes your hand as if you two are old friends. "Mr. S wants you to wear the red dress tonight, so we've selected colors that won't clash with that. He'll also have you seated next to him, to his right." Richard leans against the wall in the large dining room. "There'll be a lot of important people here tonight, Jenny. Do you think you can properly entertain?" He smiles. "You hush, Mr. Richard!" The woman scolds him, "Jenny here is as classy as they come and we all know that Mr. S only hires the finest people." She says, smiling.

At that, Mr. S walks in and looks around. "You guys have this place looking great, Rose!" He says. "Jenny, are you making yourself at home? Was anyone kind enough to show you around and tell you who will be over tonight?" He asks, eyeing Richard and Rose.

 

[JS1979]

The gardener is bringing fresh flowers to inside the house. Rose, the house-keeper takes over and putting them in two large vases, one for the dining room and the other for the living room. She is the one who's been showing me around. Much appreciated. She took me to the kitchen where the chef Lina gave me a tall glass of nice cold drink. Exotic fruity flavor. “That's passion fruit.” she said.

Back to the living room I hear Richard talking to me again. “Jenny, Do you think you can properly entertain?" The smile on his face just doesn't look right to me. What he's been saying to me just doesn't sound right to me. An accountant? I thought an accountant would be asking me the prices of those 3 items I ordered.

“Oh, here you are Mr. S....Yes, Im making myself at home.....and no, Nobody told me who will be over tonight. Maybe you would.”

 

[staylate]

"Jenny, what do you know about high finance and the sports industry?" I ask, looking you over. Richard smiles and looks at you. "The men who will be hear tonight are captains of those industries and I want them to invest in my business. But to convince them to do so, you'll need to prove to them what a great investment you are. Does that make sense?"

"These men can be...insatiable." Richard chimes in.