Meeting His New Submissive Chapter 2
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Meeting His New Submissive, Chapter 1 free porn video
It's raining cats and dogs outside and Mr. Jack Wellington is hailing a cab when he bumps into Olivia Stetson, both on their way to work. "Excuse me, Miss, would like to share this cab with me?" he asks.
"Sure, I would like that very much, Sir," she says. As the cab pulls to the curb, Mr. Wellington opens the door to allow her to get in first, holding his umbrella over her so she doesn't get too wet. As they ride to the address given the driver, Mr. Wellington turns to her.
"Where are you headed, Miss?" he asks.
"I need to go to Wellington Incorporated, Sir. That's where I work," she says, smiling politely.
"Oh really? That's where I work, too," he says, "How long have you been there?"
"For a couple of years now, I think," she replies.
"Oh? Why I haven't seen you before?" he asks.
"Well, I work on the first floor in the HR department," she says.
"Oh, I see. Well I work on the top floor," he says.
"I see, so that means you know Mr. Jack Wellington, the CEO?" she asks.
"Yes, you could say that... I am Jack Wellington. And what's your name Miss?" he asks.
"My name is Miss Olivia Stetson, Sir," she says, a little embarrassed that she didn't recognize her own boss.
"It's nice to meet you, Miss Stetson," he says.
"Please, call me Olivia. It's nice to meet you as well, Sir," she says, recovering a bit.
"Will do, Olivia. Well it looks like we are here," he says.
They get out of the cab as Mr. Wellington pays for their cab fare. He holds the door for her and they walk in, heading to the elevators. As they walk in the elevators, Mr. Wellington asks "Miss Olivia, would you like to join me today in my office?"
"No thank you, Sir, I have things and reports to do today, maybe some other time?" she says.
"I'm not taking no for an answer, Miss Olivia," he says.
"Sir, please. No disrespect intended, but I really need to get these reports done today," she says.
And with that Olivia turned and walked away from the elevator and towards her office, leaving Mr. Wellington speechless. She is the first lady to walk out on him like that.
Later that day, Olivia is working on her reports when her phone rings. She answers the phone. "Hello, Miss Olivia, It's Jack."
"Hello, Sir, how may I help you?" she says.
"Please come up to my office now," he says.
"Yes, Sir, I'll be up in couple of minutes," she says. A few moments later, Olivia reaches his office door. She knocks a couple times on the door.
"Come in," the voice behind the door says.
"Hi, Sir, you wanted to see me?" she asks.
"Yes, I did," Mr. Wellington says.
"What do you want to see me about?" she asks.
"Well, to start with, when you greet me, it's Sir from now on," he says.
"Yes, Sir. Sorry, Sir," she says, correcting herself.
"Now, that you are here, please sit down," he says. She walks over to his desk and sits in one of the big comfy leather chairs.
"Miss Olivia, how old are you?" he asks.
"I'm twenty-five, Sir."
"And are you seeing someone?" he asks.
"Sir, that is kind of personal. If you don't mind, I don't like talking about my relationships at work," she says, trying to be as polite and respectful as possible.
"Answer the question, young lady, or I will bend you over my knee and spank your ass, right here and now," he says sternly.
"Excuse me, Sir?" she says incredulously.
"You heard me. Answer my questions or I am going to spank your ass," he says again.
"I-I'm single, Sir. And I haven't been in a relationship in couple of years now," she says, faltering.
"I see," he says blankly.
"Well, Sir, I need to get back and finish these reports before they become late and I do not want to miss the deadline," she says, trying to get out of the uncomfortable conversation.
"Fine, I better see you back here when you finish these reports. Maybe we'll talk about a promotion when you return later today, Miss Stetson."
"Please, Sir, call me Olivia, I'll try to come later if not tomorrow, then," she says.
He nods and stands up, then shows her to the door. She opens the door and walks straight to the elevators, leaving him speechless again. He thinks "What's with this woman that gets his heart beating like a teenage boy?"
Now Olivia is back at her desk, finishing up on the reports and sending them off to wait for approval.
Two hours later, the reports are back and she goes upstairs to give them to Mr. Wellington. Olivia takes the elevator back up to his office. She reaches the door and knocks twice on it.
"Come in," he answers behind the door.
"Hi, Sir, I have your reports in my hand, where would like me to put them?" she asks.
"Just hand them over to me, Miss Olivia, and take a seat please," he says.
She hands the reports over to him as she takes a seat and waits for further instructions. He reads them over very carefully.
"Now, Miss Olivia, I mean Olivia, these reports are really speaking to me," he says very calmly.
"R-really, Sir?" she studders.
"Yes, ma'am," he says.
"If that's the case Sir, may I go back to my office now and finish other important files please, Sir?" she asks.
"Miss Olivia, I would like you to stay and chat with me if you don't mind. Those files back in your office can wait," he tells her.
"Yes, Sir, I'll stay then if that makes you happy," she says.
"Let's talk about a promotion," he says calmy.
"Sir, what promotion? I didn't know there is one," she says, confused.
"Now, Olivia, the promotion I am talking about is to become my secretary up here. Your office would be right outside my door and you would be responsible for all my secretarial work - you know, typing, taking dictation, filing, that sort of thing - as well as serving as a receptionist when someone comes to see me. This position also requires you to travel with me when I have out of town meetings and such. Is that a problem for you?" he explains.
"No, Sir, I can travel. But, Sir, may I ask, why me?" as her voice trails off.
"Honestly, Olivia, I have been watching your performance since you got here and you have done a splendid job for my company. I hadn't met you in person until that day in the cab, but I have been wanting to. And the reason I asked about your personal life is because I know that having a relationship makes traveling hard. But when you told me you weren't seeing anyone, I knew you were the girl for this job," he says.
"Oh, I see. Well It all sounds real nice, Sir," she says, a bit unsure still.
"Well let's see if I can sweeten the pot for you. How much am I paying you now, Olivia?" he asks.
"I am making $12.00 an hour, Sir," she says.
"And in this economy that isn't a whole lot, is it?" he says.
"No, Sir, but I manage," she says.
"Well would it be easier to 'manage' if you were to make, say $25.00 an hour?" he asks.
"Really, Sir? $25.00 an hour? To be your secretary?" she asks in disbelief.
"That's right, Olivia. Plus, you would get a travel package so the company would pick up your travel costs as well. Flights, rooms, meals, plus a little boost in pay while on business since the cost of living would be higher," he says.
"Oh, Sir, I would love to be your secretary! Oh thank you, Sir! Thank you!" she says. She jumps up to give him a hug around the neck and as she does she feels his strong arms around her waist. She feels herself dampen as he holds her and she pulls back a bit.
"Sir," she says looking in his eyes, "Would it be too out of place if I... um... kissed you?" she asks.
"Not at all, Olivia," he says. And he leans forward to kiss her tenderly.
She kisses him on the cheek. Then she looks up at him and notices his stunning yet charming blue eyes and scruffy face. He notices how beautiful and curvy she really is.
"Oh, look at the time, Sir, I need to get back to my office and finish my work for today," she says nervously.
"Oh damn, you're right, Olivia. You will be starting as my new secretary tomorrow, if that is okay with you," he says.
"Tomorrow, Sir?" she asks.
"Yes, Olivia, but wear something more eye pleasing," he replies back.
"Eye pleasing, Sir?" she asks feeling almost insulted by her clothing choice.
"I don't mean to insult your fashion sense, but as my secretary, you are a reflection of me. And because you will be working so close to me, I will be using you as sort of a salesperson for new clients," he says.
"Oh, I see," she replies, feeling a bit better.
"Plus being in this office next to me, I like you to look... well, let's just say my office needs some decoration!" he says winking at her.
"Okay, Sir, I will do my best to decorate your office," she says smiling back at him.
She walks out the door, back to her office in the HR department to finish up her work that needed to be done. Ten minutes later, she finishes her work then decides to pack up her office. She walks out of her office down to the elevator. She exits the building and to her surprise and amusement, Mr. Jack Wellington is waiting for her.
"Excuse me, Sir, why did you wait for me?" she asks.
"Well, Olivia, I thought I would take you out for a drink, if you'd like to," he says.
"Not tonight, Sir, may be some other time?" she says.
"Okay," he replies, a little disappointed.
The following day Olivia arrives at her desk when suddenly, her phone rings.
"Hello, how may I help you?" she answers.
"Hello, Olivia, can you please set up an important meeting for a VIP client?" Mr. Wellington asks.
"Yes, Sir, when will the meeting take place?" she asks.
"It's for today, and I would like you to be there for the meeting," he says.
"Yes, Sir, I'll be there. And what time will it be?" she asks.
"The client should be here in about thirty minutes," he says.
"Okay, see you soon, Sir," she hangs up the phone.
She gets up and walks over to the conference room to get everything ready. Thirty minutes isn't a lot of time but she figured this was a last-minute meeting so she has to hurry. When she walks in the conference room, Mr. Wellington was already there waiting. She sits next to him, and he tells her that she is the VIP.
"Let's discuss your promotion and your secretary job," he tells her calmly.
"Sir, what about my promotion?" she asks, confused.
"Well, Olivia, we're talking about your secretary duties," he reassures her.
"I understand, Sir," she says.
"Olivia, as my secretary I expect you to be at my beck and call, and wear something that's pleasing to the eye," he tells her.
"Sir, what?" she says, confused.
"For you to be at my beck and call and wear something that's eye catching," he repeats, "Let me explain, Olivia... your duties as my secretary will include the 'normal' secretarial duties - typing, filing, answering the phones and such. But they will also include other duties of a more personal nature."
"Sir?"
"Listen, Olivia. You are an attractive desirable woman and I would be lying if I told you I didn't entertain certain thoughts of you. Knowing that you are single and unattached only fuels those thoughts. I am a man with urges and needs that sadly go ignored far too much. It is my hope that you can help me in both the professional and personal side."
"I would like... to try, Sir." Olivia said, blushing brightly. "W-what would I have to do... personally?"
"Olivia, you would have to please me or entertain my personal clients," he reassured her.
"Sir, I don't mind pleasing you, but pleasing your clients? Sir, I'm no whore!" Olivia says.
"Oh my dear, I didn't mean it that way!" he laughs, "I just mean that they too like looking at pretty things. By dressing attractively, you make them more apt to want to do business with us."
"Oh, I see. I'm sorry I jumped to the wrong conclusions," she says.
"That's okay, my dear. I didn't make myself clear obviously," he says.
"Sir, is that it for today?" she asked.
"Yes, I think that will do for today," he says.
"Goodnight, Sir, see you tomorrow," she says.
That night Olivia looks through her closet to see what she could wear for Mr. Wellington tomorrow. She sets out something she think he might like and resolves herself to look especially nice for him.
The next day Olivia shows up to work wearing a trench coat and underneath wearing a black lacey bra and thong with garter and seamed thigh top stockings. She walks into Mr. Wellington's office making his coffee and organizing his important meetings for the day. To her surprise Mr. Wellington sneaks up behind her and gives her a soft smack on her milky ass.
"Oh, hi, Mr. Wellington!" she blushes.
"Hi, Olivia, Are you cold my dear? Should I turn up the thermostat?" he asks, concerned.
"Oh, no, Sir," she says, "I just wanted to show you what I picked out to wear for you today. You said yesterday that you wanted me to wear something pleasing to the eye. How is this?" Olivia opened her trenchcoat and let it slip off her shoulders, revealing what she had on underneath.
"Hi, Olivia, you look very stunning today," he smiles approvingly.
"Thank you, Sir," she says.
"Now because this is your first day as my new secretary, we need to clear the air about something," he says. "Ever since we first met, you have been defiant and contrary. I think we should start you off today with a good spanking!"
"Sir?" she says shocked.
"That's right, young lady. Remember our first cab ride when we met? I asked you to join me in my office. You turned me down and left me standing there. No one has ever refused me like that. Then when we began talking about this promotion and I asked you if you were single, you once again left me hurriedly and I stood there trying to figure you out. You have been quite a challenge Miss Olivia, and I think now that you have accepted the job, we need to put our relationship in order. So if you would be so kind as to bend over my desk, we shall set things right," he says, waving his arm to his desk.
"But, Sir... I..." she says, anxious at this new turn.
"Miss Olivia, if you do not want this promotion, I'm sure I can find another girl who would be most appreciative of a chance to work up here with me!" he says sternly. Mr. Wellington is getting tired of being turned down by an employee - especially one who he has tried to be so nice to.
"No, Sir, I do want this promotion," she says, hanging her head. "I'm sorry I have been so difficult." She gets up and walks over to the desk, laying over it as he directs.
"That's better," he says. He walks around his desk and gets something out of his drawer. "This looks like a regular ping pong paddle so if anyone sees it, I just tell them I love the game. However for you, it will have a slightly different purpose today!"
Without any further explanation or discussion, he draws back and gives her the first smack.
"Oh!" Olivia jumps as she feels the paddle land on her soft creamy ass. A bright pink patch quickly develops where the paddle struck. Mr. Wellington follows up with a second smack to her other cheek with similar results.
"My, my, your ass certainly responds well to my paddle, my dear!" he says as he caresses her ass.
"Ohhh..." Olivia mewls as she feels him rubbing her ass. She wriggles her ass and pushes back against his hand.
Mr. Wellington puts one hand on the small of her back right where it begins to flare out to become her ass. Holding her down on the desk, he begins a quick but steady rhythm of smacks to her ass, alternating sides and not taking a break between. The sound of the paddle striking soft flesh fills the room accompanied by moans, then whimpers and finally cries as the paddle does its work.
After an agonizing twenty smacks, ten on each asscheek, he stops. Olivia lays moaning on his desk, her ass bright red now and hot to the touch. He rubs her ass, soothing it when he feels a dampness.
"What have we here, Olivia? Do I feel a wet pussy? Don't tell me you actually liked getting spanked?" he asks chuckling. He begins fondling her and playing with her pussy, rolling her swollen pussy lips between his fingers and lightly tugging on them. Then he slides a finger between her lips and strokes the sides of her entrance. Olivia moans and sucks in a breath as she feels him at the very door to her womanhood.
"Should I go further, my dear?" he asks.
"Please..." she moans, pushing back against his hand and trying to get him deeper inside her. He obliges her by shoving not one, but two fingers deep into her wet hole. He begins sawing into her like he's trying to cut her in two and Olivia responds by grabbing the edge of the desk, raising her head and moaning loudly. He can see her legs trembling as he works her pussy furiously. With the hand on top of her ass, he uses his thumb to circle her tight crinkled asshole, rubbing the little star, and as she responds, finally pushing his thumb into her ass up to the first knuckle.
"Ohhh, God, Mr. Wellington..." she moans lustfully. She raises up on tip-toe as his thumb pushes past her ring. Meanwhile his other hand continues sawing in and out of her now dripping pussy. Olivia is beside herself, moaning and wriggling, twisting in order for Mr. Wellington's hand to reach just where she needed it. Olivia grabs the edges of the desk as she prepares for lift off, blasting off to her first good orgasm in a very long time.
"Ohhh, God, Sir! I'm cumming, Oh please, I'm cumming!" she moans, as she feels the pressure getting to be too much. Mr. Wellington pulls his hands out instantly upon her announcement.
Olivia collapses on the desk, panting for a couple moments to catch her breath. Then she turns around. "Why did you stop, Sir? I was just about to cum! I was right there, Sir!" she whines.
"Well, my wet little slut, first off, I wasn't ready for you to cum just yet. I want to build up your orgasm so that when I do grant it, you will remember it and remember who gave it to you. I know that you need to cum very badly - that you haven't had sex in a long time. That is not going to be a problem for you anymore my dear. However, I don't want you forgetting my generosity and kindness either. Just because you are getting it regularly, is no cause to take it for granted!
"Secondly, you didn't ask to cum, you merely announced it. From now on, you must tell me when you are getting close to cumming and then ask me to allow you. This way I know that you remember the source of your pleasure - me. I will grant your orgasms when and how I deem it appropriate at the time. You will accept my gift graciously and thankfully, understand?"
"Yes, Sir," she said. finally getting her breathing under control.
"I am not a harsh man, Olivia. If I were, you would still be working on the first floor and still be putting out. Or you would be standing in a very long unemployment line. But instead I have moved you up here and given you a very generous raise. For that, I merely require you to be thankful and appreciative of my attentions," he says.
"Yes, Sir, I am thankful for all that you've done, really, Sir," she says.
"Olivia, I can promise you many wonderful orgasms and a very good working environment up here. I treat my people well and I treat those who appreciate it and show their gratitude to me even better. You work with me and I will see that you are very well cared for, my beauty," he says.
"Yes, Sir. I do want to enjoy working up here with you," she says.
"I'm glad to hear that, Olivia," he says. "Stay right there for a moment." He walks across the room to the coat closet and in the corner, he pulls out a small brown suitcase. Setting it on another chair he unlocks it and pulls something out of the suitcase.
"Have you ever heard of a Hitachi Magic Wand, Olivia? Do you know what they do?" he asks her.
"No, Sir," she says.
"Well, the Hitachi Magic Wand is a 'personal massager'... it is marketed as a massager for sore muscles such as your neck and shoulders. However, it is rarely used for those muscles, having found a more useful and pleasant purpose massaging a young woman's cunt muscles!" he says.
"Ohhh..." Olivia moans. She has never heard of this device and never seen it in action, but the thoughts of it buzzing against her already aroused pussy were enough to send a shudder through her.
"Indeed, my dear. And just wait 'til you see how wonderfully effective it does that job!" he says. He plugs the cord into a nearby outlet then steps up behind Olivia. Reaching forward he grabs a handful of her soft brown hair and hauls her upright, holding her in place against him. He reaches around her with the other hand and roughly pulls her bra up and over her young full tits, exposing them. He pinches and tugs at ther tender nipples, getting them hard and erect as she moans her delight.
Once her nipples are hard and fat, he reaches down for the Magic Wand and clicks it on. Rubbing the buzzing head against her nipples makes Olivia so weak-kneed she almost falls except for Mr. Wellington standing behind her. She reaches up with her hand to feel the device, but he pulls it away quickly.
"Keep those hands down young lady or the game is over!" he chuckles. She puts her hands back down on the desk obediently, not wanting him to stop with the Wand.
"Much better. That feels nice doesn't it, my pretty slut? The vibrations on your hard nipples feels so good... just imagine what this will feel like against that pretty pussy!" he whispers deep in her ear.
Olivia is already imagining it and her pussy is drooling in eager anticipation. She could feel the wetness running down her legs and getting the tops of her stockings wet.
Ohhh, Sirrr..." she moans, swaying on trembling legs that can barely hold her upright.
With her nipples so hard and erect now that they hurt, he pushs her back down on the desk, spreading her legs wide. Olivia is thankful for the desk, grabbing and tightly hugging it.
Mr. Wellington moves the buzzing device down and runs it slowly up her inner thigh. Starting just above her knee, he moves it slowly up the tender inside of her right thigh. As the buzzing gets closer to her center, Olivia begins moaning, knowing that when it reaches her sopping pussy, it will drive her over the edge. The device moves higher and her heart begins to race. She is leaking like a broken pipe now and she grips the edge of the desk, watching her knuckles turn white with the effort.
As the Wand gets perilously close to her dripping pussy lips, Olivia sucks in a breath preparing herself for what she knows is coming. But she will have to wait a bit longer as Mr. Wellington pulls the Wand away at the last moment, enjoying Olivia's groan of disappointment.
He moves the Wand over to her left leg, again starting just above her knee and moving slowly up the inside of her leg. Once again she begins to get more and more turned on the higher the device gets. Closer and closer to her greedy pussy, the teasing demon rises. She wills it to touch her, to grant her the release she craves so desperately. But once again she is denied.
Olivia stomps her feet, whimpering in protest of this cruel torment, but just at her most dejected and forlorn, Mr. Wellington shoves the buzzing head of the Wand hard against her pussy, pushing it past her outer lips to rest directly at her vaginal opening.
"OHHHMYYYGAWWD!" Olivia screams out as the buzzing device attacks her pussy. Mr. Wellington watches as Olivia's body tenses - an involuntary reaction to the vibrator's assault. Mr. Wellington pushes his thumb back into her ass as before and the combination is devastating.
"Mr Wellington! Oh my God, Sir, Oh please please may I cum? Please I need to cum, Please, Sir!" she wails. The desperation and urgency is clear to him. He knows that she won't be able to hold it back any longer, no matter what he says. So rather than get her in trouble again, he is merciful.
"Cum, then slut. Cum for me NOW!" he commands.
"OHHHSIRRR!! OHMYGOD!!" she screams as she pours her juices out, running down her legs and spilling onto the hardwood floor under her. She cums and cums seemingly forever as he keeps the Wand firmly against her clit and pussy lips, moving it around to make sure she won't get used to it. She stomps her feet and writhes as one orgasm slams into another and she just keeps pouring out her sweet nectar.
Finally, she is completely drained and lays limply over the desk. He pulls the Wand away and looks at the sweat and cum drenched body, quivering as it drapes over his desk, panting like an overheated dog and moaning softly to herself.
Mr. Wellington is pleased with himself, but he also realizes that he hasn't enjoyed her yet. So without giving her much time to recover and recuperate, he sweeps her feet up and lays them on the desk flipping her onto her back and pulling her to the edge of the desk so her head hangs over the edge.
"Open that pretty mouth slut, I have something for it!" he says, lightly slapping her face. Olivia opens her mouth almost automatically and he shoves his hard, thick cock into it. He pushes forward until he feels himself at the back of her throat and she begins to gag. He backs up a bit so she won't gag and she begins to suck his cock as he pumps in and out of her warm, wet mouth.
"I can see we are going to have to work on your deepthroating skills," he says, "You can barely get five inches of me in your mouth! You are going to have to learn to take me down your throat if you expect to get all of me in that sweet little mouth!"
Olivia does her best, sucking and licking his cock as he pumps in and out of her mouth. She keeps her lips sealed tightly against his shaft and puts her hands on the backs of his thighs to keep him close to her. Mr. Wellington uses her exposed body as his plaything slapping her tits and figering her pussy as she works his cock, moaning and making those sexy guk-guk-guk noises as he moves in and out of her mouth.
Mr. Wellington can feel his orgasm churning in his balls. He isn't sure if he should just stay where he is and shoot his load down her throat, or pull out and blast her face and tits. Some women are swallowers and some are not, and he isn't sure if she can handle the massive load he is brewing. He opts to play it safe this first time and just as he feels himself cresting, he pulls out of her mouth just as the first jets erupt from his cock. He shoots stream after stream onto her young tits, her face, and some further down her belly. He did have a huge load and he explodes with such force it makes his knees weak, but he keeps shooting onto Olivia's face and tits until his balls are empty.
Olivia lay there on the desk panting and covered in cum. She looks and feels just like a whore and she loves it. Mr. Wellington puts his softening cock back in her slutty mouth. "Clean me off slut!" he says and she gratefully licks and sucks the last of his cum from his cock, making sure he comes out squeaky clean.
Mr. Wellington gives her a few minutes to fully recover this time before helping her down from the desk. "Go on into the bathroom and get cleaned up, we still have business to attend to today!" he says.
"Yes, Sir. Thank you, Sir," she says and she walks into the bathroom, still a bit wobbly, but managing to make it on her own.
"Sure, I would like that very much, Sir," she says. As the cab pulls to the curb, Mr. Wellington opens the door to allow her to get in first, holding his umbrella over her so she doesn't get too wet. As they ride to the address given the driver, Mr. Wellington turns to her.
"Where are you headed, Miss?" he asks.
"I need to go to Wellington Incorporated, Sir. That's where I work," she says, smiling politely.
"Oh really? That's where I work, too," he says, "How long have you been there?"
"For a couple of years now, I think," she replies.
"Oh? Why I haven't seen you before?" he asks.
"Well, I work on the first floor in the HR department," she says.
"Oh, I see. Well I work on the top floor," he says.
"I see, so that means you know Mr. Jack Wellington, the CEO?" she asks.
"Yes, you could say that... I am Jack Wellington. And what's your name Miss?" he asks.
"My name is Miss Olivia Stetson, Sir," she says, a little embarrassed that she didn't recognize her own boss.
"It's nice to meet you, Miss Stetson," he says.
"Please, call me Olivia. It's nice to meet you as well, Sir," she says, recovering a bit.
"Will do, Olivia. Well it looks like we are here," he says.
They get out of the cab as Mr. Wellington pays for their cab fare. He holds the door for her and they walk in, heading to the elevators. As they walk in the elevators, Mr. Wellington asks "Miss Olivia, would you like to join me today in my office?"
"No thank you, Sir, I have things and reports to do today, maybe some other time?" she says.
"I'm not taking no for an answer, Miss Olivia," he says.
"Sir, please. No disrespect intended, but I really need to get these reports done today," she says.
And with that Olivia turned and walked away from the elevator and towards her office, leaving Mr. Wellington speechless. She is the first lady to walk out on him like that.
Later that day, Olivia is working on her reports when her phone rings. She answers the phone. "Hello, Miss Olivia, It's Jack."
"Hello, Sir, how may I help you?" she says.
"Please come up to my office now," he says.
"Yes, Sir, I'll be up in couple of minutes," she says. A few moments later, Olivia reaches his office door. She knocks a couple times on the door.
"Come in," the voice behind the door says.
"Hi, Sir, you wanted to see me?" she asks.
"Yes, I did," Mr. Wellington says.
"What do you want to see me about?" she asks.
"Well, to start with, when you greet me, it's Sir from now on," he says.
"Yes, Sir. Sorry, Sir," she says, correcting herself.
"Now, that you are here, please sit down," he says. She walks over to his desk and sits in one of the big comfy leather chairs.
"Miss Olivia, how old are you?" he asks.
"I'm twenty-five, Sir."
"And are you seeing someone?" he asks.
"Sir, that is kind of personal. If you don't mind, I don't like talking about my relationships at work," she says, trying to be as polite and respectful as possible.
"Answer the question, young lady, or I will bend you over my knee and spank your ass, right here and now," he says sternly.
"Excuse me, Sir?" she says incredulously.
"You heard me. Answer my questions or I am going to spank your ass," he says again.
"I-I'm single, Sir. And I haven't been in a relationship in couple of years now," she says, faltering.
"I see," he says blankly.
"Well, Sir, I need to get back and finish these reports before they become late and I do not want to miss the deadline," she says, trying to get out of the uncomfortable conversation.
"Fine, I better see you back here when you finish these reports. Maybe we'll talk about a promotion when you return later today, Miss Stetson."
"Please, Sir, call me Olivia, I'll try to come later if not tomorrow, then," she says.
He nods and stands up, then shows her to the door. She opens the door and walks straight to the elevators, leaving him speechless again. He thinks "What's with this woman that gets his heart beating like a teenage boy?"
Now Olivia is back at her desk, finishing up on the reports and sending them off to wait for approval.
Two hours later, the reports are back and she goes upstairs to give them to Mr. Wellington. Olivia takes the elevator back up to his office. She reaches the door and knocks twice on it.
"Come in," he answers behind the door.
"Hi, Sir, I have your reports in my hand, where would like me to put them?" she asks.
"Just hand them over to me, Miss Olivia, and take a seat please," he says.
She hands the reports over to him as she takes a seat and waits for further instructions. He reads them over very carefully.
"Now, Miss Olivia, I mean Olivia, these reports are really speaking to me," he says very calmly.
"R-really, Sir?" she studders.
"Yes, ma'am," he says.
"If that's the case Sir, may I go back to my office now and finish other important files please, Sir?" she asks.
"Miss Olivia, I would like you to stay and chat with me if you don't mind. Those files back in your office can wait," he tells her.
"Yes, Sir, I'll stay then if that makes you happy," she says.
"Let's talk about a promotion," he says calmy.
"Sir, what promotion? I didn't know there is one," she says, confused.
"Now, Olivia, the promotion I am talking about is to become my secretary up here. Your office would be right outside my door and you would be responsible for all my secretarial work - you know, typing, taking dictation, filing, that sort of thing - as well as serving as a receptionist when someone comes to see me. This position also requires you to travel with me when I have out of town meetings and such. Is that a problem for you?" he explains.
"No, Sir, I can travel. But, Sir, may I ask, why me?" as her voice trails off.
"Honestly, Olivia, I have been watching your performance since you got here and you have done a splendid job for my company. I hadn't met you in person until that day in the cab, but I have been wanting to. And the reason I asked about your personal life is because I know that having a relationship makes traveling hard. But when you told me you weren't seeing anyone, I knew you were the girl for this job," he says.
"Oh, I see. Well It all sounds real nice, Sir," she says, a bit unsure still.
"Well let's see if I can sweeten the pot for you. How much am I paying you now, Olivia?" he asks.
"I am making $12.00 an hour, Sir," she says.
"And in this economy that isn't a whole lot, is it?" he says.
"No, Sir, but I manage," she says.
"Well would it be easier to 'manage' if you were to make, say $25.00 an hour?" he asks.
"Really, Sir? $25.00 an hour? To be your secretary?" she asks in disbelief.
"That's right, Olivia. Plus, you would get a travel package so the company would pick up your travel costs as well. Flights, rooms, meals, plus a little boost in pay while on business since the cost of living would be higher," he says.
"Oh, Sir, I would love to be your secretary! Oh thank you, Sir! Thank you!" she says. She jumps up to give him a hug around the neck and as she does she feels his strong arms around her waist. She feels herself dampen as he holds her and she pulls back a bit.
"Sir," she says looking in his eyes, "Would it be too out of place if I... um... kissed you?" she asks.
"Not at all, Olivia," he says. And he leans forward to kiss her tenderly.
She kisses him on the cheek. Then she looks up at him and notices his stunning yet charming blue eyes and scruffy face. He notices how beautiful and curvy she really is.
"Oh, look at the time, Sir, I need to get back to my office and finish my work for today," she says nervously.
"Oh damn, you're right, Olivia. You will be starting as my new secretary tomorrow, if that is okay with you," he says.
"Tomorrow, Sir?" she asks.
"Yes, Olivia, but wear something more eye pleasing," he replies back.
"Eye pleasing, Sir?" she asks feeling almost insulted by her clothing choice.
"I don't mean to insult your fashion sense, but as my secretary, you are a reflection of me. And because you will be working so close to me, I will be using you as sort of a salesperson for new clients," he says.
"Oh, I see," she replies, feeling a bit better.
"Plus being in this office next to me, I like you to look... well, let's just say my office needs some decoration!" he says winking at her.
"Okay, Sir, I will do my best to decorate your office," she says smiling back at him.
She walks out the door, back to her office in the HR department to finish up her work that needed to be done. Ten minutes later, she finishes her work then decides to pack up her office. She walks out of her office down to the elevator. She exits the building and to her surprise and amusement, Mr. Jack Wellington is waiting for her.
"Excuse me, Sir, why did you wait for me?" she asks.
"Well, Olivia, I thought I would take you out for a drink, if you'd like to," he says.
"Not tonight, Sir, may be some other time?" she says.
"Okay," he replies, a little disappointed.
The following day Olivia arrives at her desk when suddenly, her phone rings.
"Hello, how may I help you?" she answers.
"Hello, Olivia, can you please set up an important meeting for a VIP client?" Mr. Wellington asks.
"Yes, Sir, when will the meeting take place?" she asks.
"It's for today, and I would like you to be there for the meeting," he says.
"Yes, Sir, I'll be there. And what time will it be?" she asks.
"The client should be here in about thirty minutes," he says.
"Okay, see you soon, Sir," she hangs up the phone.
She gets up and walks over to the conference room to get everything ready. Thirty minutes isn't a lot of time but she figured this was a last-minute meeting so she has to hurry. When she walks in the conference room, Mr. Wellington was already there waiting. She sits next to him, and he tells her that she is the VIP.
"Let's discuss your promotion and your secretary job," he tells her calmly.
"Sir, what about my promotion?" she asks, confused.
"Well, Olivia, we're talking about your secretary duties," he reassures her.
"I understand, Sir," she says.
"Olivia, as my secretary I expect you to be at my beck and call, and wear something that's pleasing to the eye," he tells her.
"Sir, what?" she says, confused.
"For you to be at my beck and call and wear something that's eye catching," he repeats, "Let me explain, Olivia... your duties as my secretary will include the 'normal' secretarial duties - typing, filing, answering the phones and such. But they will also include other duties of a more personal nature."
"Sir?"
"Listen, Olivia. You are an attractive desirable woman and I would be lying if I told you I didn't entertain certain thoughts of you. Knowing that you are single and unattached only fuels those thoughts. I am a man with urges and needs that sadly go ignored far too much. It is my hope that you can help me in both the professional and personal side."
"I would like... to try, Sir." Olivia said, blushing brightly. "W-what would I have to do... personally?"
"Olivia, you would have to please me or entertain my personal clients," he reassured her.
"Sir, I don't mind pleasing you, but pleasing your clients? Sir, I'm no whore!" Olivia says.
"Oh my dear, I didn't mean it that way!" he laughs, "I just mean that they too like looking at pretty things. By dressing attractively, you make them more apt to want to do business with us."
"Oh, I see. I'm sorry I jumped to the wrong conclusions," she says.
"That's okay, my dear. I didn't make myself clear obviously," he says.
"Sir, is that it for today?" she asked.
"Yes, I think that will do for today," he says.
"Goodnight, Sir, see you tomorrow," she says.
That night Olivia looks through her closet to see what she could wear for Mr. Wellington tomorrow. She sets out something she think he might like and resolves herself to look especially nice for him.
The next day Olivia shows up to work wearing a trench coat and underneath wearing a black lacey bra and thong with garter and seamed thigh top stockings. She walks into Mr. Wellington's office making his coffee and organizing his important meetings for the day. To her surprise Mr. Wellington sneaks up behind her and gives her a soft smack on her milky ass.
"Oh, hi, Mr. Wellington!" she blushes.
"Hi, Olivia, Are you cold my dear? Should I turn up the thermostat?" he asks, concerned.
"Oh, no, Sir," she says, "I just wanted to show you what I picked out to wear for you today. You said yesterday that you wanted me to wear something pleasing to the eye. How is this?" Olivia opened her trenchcoat and let it slip off her shoulders, revealing what she had on underneath.
"Hi, Olivia, you look very stunning today," he smiles approvingly.
"Thank you, Sir," she says.
"Now because this is your first day as my new secretary, we need to clear the air about something," he says. "Ever since we first met, you have been defiant and contrary. I think we should start you off today with a good spanking!"
"Sir?" she says shocked.
"That's right, young lady. Remember our first cab ride when we met? I asked you to join me in my office. You turned me down and left me standing there. No one has ever refused me like that. Then when we began talking about this promotion and I asked you if you were single, you once again left me hurriedly and I stood there trying to figure you out. You have been quite a challenge Miss Olivia, and I think now that you have accepted the job, we need to put our relationship in order. So if you would be so kind as to bend over my desk, we shall set things right," he says, waving his arm to his desk.
"But, Sir... I..." she says, anxious at this new turn.
"Miss Olivia, if you do not want this promotion, I'm sure I can find another girl who would be most appreciative of a chance to work up here with me!" he says sternly. Mr. Wellington is getting tired of being turned down by an employee - especially one who he has tried to be so nice to.
"No, Sir, I do want this promotion," she says, hanging her head. "I'm sorry I have been so difficult." She gets up and walks over to the desk, laying over it as he directs.
"That's better," he says. He walks around his desk and gets something out of his drawer. "This looks like a regular ping pong paddle so if anyone sees it, I just tell them I love the game. However for you, it will have a slightly different purpose today!"
Without any further explanation or discussion, he draws back and gives her the first smack.
"Oh!" Olivia jumps as she feels the paddle land on her soft creamy ass. A bright pink patch quickly develops where the paddle struck. Mr. Wellington follows up with a second smack to her other cheek with similar results.
"My, my, your ass certainly responds well to my paddle, my dear!" he says as he caresses her ass.
"Ohhh..." Olivia mewls as she feels him rubbing her ass. She wriggles her ass and pushes back against his hand.
Mr. Wellington puts one hand on the small of her back right where it begins to flare out to become her ass. Holding her down on the desk, he begins a quick but steady rhythm of smacks to her ass, alternating sides and not taking a break between. The sound of the paddle striking soft flesh fills the room accompanied by moans, then whimpers and finally cries as the paddle does its work.
After an agonizing twenty smacks, ten on each asscheek, he stops. Olivia lays moaning on his desk, her ass bright red now and hot to the touch. He rubs her ass, soothing it when he feels a dampness.
"What have we here, Olivia? Do I feel a wet pussy? Don't tell me you actually liked getting spanked?" he asks chuckling. He begins fondling her and playing with her pussy, rolling her swollen pussy lips between his fingers and lightly tugging on them. Then he slides a finger between her lips and strokes the sides of her entrance. Olivia moans and sucks in a breath as she feels him at the very door to her womanhood.
"Should I go further, my dear?" he asks.
"Please..." she moans, pushing back against his hand and trying to get him deeper inside her. He obliges her by shoving not one, but two fingers deep into her wet hole. He begins sawing into her like he's trying to cut her in two and Olivia responds by grabbing the edge of the desk, raising her head and moaning loudly. He can see her legs trembling as he works her pussy furiously. With the hand on top of her ass, he uses his thumb to circle her tight crinkled asshole, rubbing the little star, and as she responds, finally pushing his thumb into her ass up to the first knuckle.
"Ohhh, God, Mr. Wellington..." she moans lustfully. She raises up on tip-toe as his thumb pushes past her ring. Meanwhile his other hand continues sawing in and out of her now dripping pussy. Olivia is beside herself, moaning and wriggling, twisting in order for Mr. Wellington's hand to reach just where she needed it. Olivia grabs the edges of the desk as she prepares for lift off, blasting off to her first good orgasm in a very long time.
"Ohhh, God, Sir! I'm cumming, Oh please, I'm cumming!" she moans, as she feels the pressure getting to be too much. Mr. Wellington pulls his hands out instantly upon her announcement.
Olivia collapses on the desk, panting for a couple moments to catch her breath. Then she turns around. "Why did you stop, Sir? I was just about to cum! I was right there, Sir!" she whines.
"Well, my wet little slut, first off, I wasn't ready for you to cum just yet. I want to build up your orgasm so that when I do grant it, you will remember it and remember who gave it to you. I know that you need to cum very badly - that you haven't had sex in a long time. That is not going to be a problem for you anymore my dear. However, I don't want you forgetting my generosity and kindness either. Just because you are getting it regularly, is no cause to take it for granted!
"Secondly, you didn't ask to cum, you merely announced it. From now on, you must tell me when you are getting close to cumming and then ask me to allow you. This way I know that you remember the source of your pleasure - me. I will grant your orgasms when and how I deem it appropriate at the time. You will accept my gift graciously and thankfully, understand?"
"Yes, Sir," she said. finally getting her breathing under control.
"I am not a harsh man, Olivia. If I were, you would still be working on the first floor and still be putting out. Or you would be standing in a very long unemployment line. But instead I have moved you up here and given you a very generous raise. For that, I merely require you to be thankful and appreciative of my attentions," he says.
"Yes, Sir, I am thankful for all that you've done, really, Sir," she says.
"Olivia, I can promise you many wonderful orgasms and a very good working environment up here. I treat my people well and I treat those who appreciate it and show their gratitude to me even better. You work with me and I will see that you are very well cared for, my beauty," he says.
"Yes, Sir. I do want to enjoy working up here with you," she says.
"I'm glad to hear that, Olivia," he says. "Stay right there for a moment." He walks across the room to the coat closet and in the corner, he pulls out a small brown suitcase. Setting it on another chair he unlocks it and pulls something out of the suitcase.
"Have you ever heard of a Hitachi Magic Wand, Olivia? Do you know what they do?" he asks her.
"No, Sir," she says.
"Well, the Hitachi Magic Wand is a 'personal massager'... it is marketed as a massager for sore muscles such as your neck and shoulders. However, it is rarely used for those muscles, having found a more useful and pleasant purpose massaging a young woman's cunt muscles!" he says.
"Ohhh..." Olivia moans. She has never heard of this device and never seen it in action, but the thoughts of it buzzing against her already aroused pussy were enough to send a shudder through her.
"Indeed, my dear. And just wait 'til you see how wonderfully effective it does that job!" he says. He plugs the cord into a nearby outlet then steps up behind Olivia. Reaching forward he grabs a handful of her soft brown hair and hauls her upright, holding her in place against him. He reaches around her with the other hand and roughly pulls her bra up and over her young full tits, exposing them. He pinches and tugs at ther tender nipples, getting them hard and erect as she moans her delight.
Once her nipples are hard and fat, he reaches down for the Magic Wand and clicks it on. Rubbing the buzzing head against her nipples makes Olivia so weak-kneed she almost falls except for Mr. Wellington standing behind her. She reaches up with her hand to feel the device, but he pulls it away quickly.
"Keep those hands down young lady or the game is over!" he chuckles. She puts her hands back down on the desk obediently, not wanting him to stop with the Wand.
"Much better. That feels nice doesn't it, my pretty slut? The vibrations on your hard nipples feels so good... just imagine what this will feel like against that pretty pussy!" he whispers deep in her ear.
Olivia is already imagining it and her pussy is drooling in eager anticipation. She could feel the wetness running down her legs and getting the tops of her stockings wet.
Ohhh, Sirrr..." she moans, swaying on trembling legs that can barely hold her upright.
With her nipples so hard and erect now that they hurt, he pushs her back down on the desk, spreading her legs wide. Olivia is thankful for the desk, grabbing and tightly hugging it.
Mr. Wellington moves the buzzing device down and runs it slowly up her inner thigh. Starting just above her knee, he moves it slowly up the tender inside of her right thigh. As the buzzing gets closer to her center, Olivia begins moaning, knowing that when it reaches her sopping pussy, it will drive her over the edge. The device moves higher and her heart begins to race. She is leaking like a broken pipe now and she grips the edge of the desk, watching her knuckles turn white with the effort.
As the Wand gets perilously close to her dripping pussy lips, Olivia sucks in a breath preparing herself for what she knows is coming. But she will have to wait a bit longer as Mr. Wellington pulls the Wand away at the last moment, enjoying Olivia's groan of disappointment.
He moves the Wand over to her left leg, again starting just above her knee and moving slowly up the inside of her leg. Once again she begins to get more and more turned on the higher the device gets. Closer and closer to her greedy pussy, the teasing demon rises. She wills it to touch her, to grant her the release she craves so desperately. But once again she is denied.
Olivia stomps her feet, whimpering in protest of this cruel torment, but just at her most dejected and forlorn, Mr. Wellington shoves the buzzing head of the Wand hard against her pussy, pushing it past her outer lips to rest directly at her vaginal opening.
"OHHHMYYYGAWWD!" Olivia screams out as the buzzing device attacks her pussy. Mr. Wellington watches as Olivia's body tenses - an involuntary reaction to the vibrator's assault. Mr. Wellington pushes his thumb back into her ass as before and the combination is devastating.
"Mr Wellington! Oh my God, Sir, Oh please please may I cum? Please I need to cum, Please, Sir!" she wails. The desperation and urgency is clear to him. He knows that she won't be able to hold it back any longer, no matter what he says. So rather than get her in trouble again, he is merciful.
"Cum, then slut. Cum for me NOW!" he commands.
"OHHHSIRRR!! OHMYGOD!!" she screams as she pours her juices out, running down her legs and spilling onto the hardwood floor under her. She cums and cums seemingly forever as he keeps the Wand firmly against her clit and pussy lips, moving it around to make sure she won't get used to it. She stomps her feet and writhes as one orgasm slams into another and she just keeps pouring out her sweet nectar.
Finally, she is completely drained and lays limply over the desk. He pulls the Wand away and looks at the sweat and cum drenched body, quivering as it drapes over his desk, panting like an overheated dog and moaning softly to herself.
Mr. Wellington is pleased with himself, but he also realizes that he hasn't enjoyed her yet. So without giving her much time to recover and recuperate, he sweeps her feet up and lays them on the desk flipping her onto her back and pulling her to the edge of the desk so her head hangs over the edge.
"Open that pretty mouth slut, I have something for it!" he says, lightly slapping her face. Olivia opens her mouth almost automatically and he shoves his hard, thick cock into it. He pushes forward until he feels himself at the back of her throat and she begins to gag. He backs up a bit so she won't gag and she begins to suck his cock as he pumps in and out of her warm, wet mouth.
"I can see we are going to have to work on your deepthroating skills," he says, "You can barely get five inches of me in your mouth! You are going to have to learn to take me down your throat if you expect to get all of me in that sweet little mouth!"
Olivia does her best, sucking and licking his cock as he pumps in and out of her mouth. She keeps her lips sealed tightly against his shaft and puts her hands on the backs of his thighs to keep him close to her. Mr. Wellington uses her exposed body as his plaything slapping her tits and figering her pussy as she works his cock, moaning and making those sexy guk-guk-guk noises as he moves in and out of her mouth.
Mr. Wellington can feel his orgasm churning in his balls. He isn't sure if he should just stay where he is and shoot his load down her throat, or pull out and blast her face and tits. Some women are swallowers and some are not, and he isn't sure if she can handle the massive load he is brewing. He opts to play it safe this first time and just as he feels himself cresting, he pulls out of her mouth just as the first jets erupt from his cock. He shoots stream after stream onto her young tits, her face, and some further down her belly. He did have a huge load and he explodes with such force it makes his knees weak, but he keeps shooting onto Olivia's face and tits until his balls are empty.
Olivia lay there on the desk panting and covered in cum. She looks and feels just like a whore and she loves it. Mr. Wellington puts his softening cock back in her slutty mouth. "Clean me off slut!" he says and she gratefully licks and sucks the last of his cum from his cock, making sure he comes out squeaky clean.
Mr. Wellington gives her a few minutes to fully recover this time before helping her down from the desk. "Go on into the bathroom and get cleaned up, we still have business to attend to today!" he says.
"Yes, Sir. Thank you, Sir," she says and she walks into the bathroom, still a bit wobbly, but managing to make it on her own.
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