Do It! - Cover

Do It!

Copyright© 2010 by Thesandman

Chapter 1

Erotica Sex Story: Chapter 1 - Chris Matthews is about to embark on a life changing experience.

Caution: This Erotica Sex Story contains strong sexual content, including Reluctant   BDSM   DomSub   Spanking   Rough   Light Bond   Humiliation   Oral Sex   Anal Sex   Masturbation   Sex Toys   Squirting   Spitting   Exhibitionism   Voyeurism  

I had met Ted Mason when he'd been hired to come in and do some consulting on a major company merger I myself had been working on. His reputation preceded him, both in his almost ruthless review of a Company's organization, as well as his penchant for the ladies. His photo appearing quite frequently in the society pages of the paper.

He had one of those rough, chiseled looks about him, handsome beyond measure. Just over six feet tall with wavy black hair, cobalt blue eyes, and a body that one could see even through a three-piece suit he took care of. One could only imagine what else he was in possession of that the women all seemed anxious to want to have a look at.

When I heard he'd been hired to come in and do some consulting prior to the anticipated merger, I was more than a little bit nervous, as I'd be working very closely with him during the course of the time he would be here.

"Mr. Mason? This is Chris Mathews, she'll be your liaison and will be the one to show you around and inform you on all the area departments, procedures and organizational structuring," My boss Mike Bradford said introducing the two of us.

Having heard about his reputation long before hand, I had purposely dressed for the occasion. Not that I wore inappropriate attire into work anyway, because I didn't. But the last thing I wanted to do, was to wear anything that might be construed as sexual in any way. It was for that reason I had purposely worn a women's business suit, white high necked collar blouse with my long reddish brown hair pinned up rather than wearing it down as I very often did. Even my business jacket did a fairly good job of concealing what I felt was one of my more prominent attributes, C cup breasts that were full and as I'd been told on more than one occasion, damn near perfect in shape.

I knew going in that I'd end up working late at night, one or two weekends in fact though I'd be compensated for my efforts accordingly. Even so, I wasn't too keen on having to do so, working that closely and alone with the infamous Ted Mason. Though he lived in the suburbs, rather than commute back and forth every day, he had taken a suite in one of the nearby luxurious hotels where he would very often work late into the night. When the time came, which I knew it eventually would, he had invited me up to his suite one evening to go over a few final documents with him.

To be perfectly honest, I was nervous as hell. Being alone in his room with him, though he'd not once made a pass at me ... up until now anyway, gave me cause for concern. Having ordered room service, we ate while going over the papers of the merge. I was again surprised that he kept it formal, almost too formal, which in a strange way now irritated me as for the first time since we'd started working together, I had actually let my hair down. Not only that, but I'd even allowed myself to wear a blouse that did little if anything to hide my more than ample breasts. Not once however did I see him attempt to steal a glance, or look at me any place other than in my eyes whenever we spoke.

By the time I had finally left, I'd decided that perhaps I just wasn't in his class, didn't live up to his standards and expectations, and was somewhat relieved that our less than exciting journey together was over.

A month later the company I worked for merged. Everyone said it was one of the smoothest, easiest merges to ever take place with a Billion dollar company. Few realized or knew about the long tedious hours that I had personally put into it myself, except for my boss perhaps, who'd given me a rather nice bonus, and a few extra days off in order to rest and recuperate.

I was doing just that at home, lying out by the pool taking in some much needed sun and actually relaxing after several weeks of hard grueling work when a florist stopped by. Having tried the door-bell out front, with no answer, he had come around the back hoping to at least leave the arrangement in a safe place, only then noticing me as I lay out by the pool, topless I might add as he called out to me.

"Ah, excuse me? Miss? Flowers!"

It was funny, normally I might have panicked, even been a little embarrassed to have been caught in such a compromising position. But I had been so frustrated lately, sexually ... that I actually found enjoyment in simply standing up, walking over, and then signing for the delivery as the poor driver stood there with his mouth half agape, staring at my exposed tits.

"Thank you, I said taking the arrangement. Let me get you a tip from my purse."

He smiled, "No thanks ... not necessary, you've already given me one ... a nice one, thank you!"

I smiled back, appreciating the compliment, something I hadn't had in a while, and then walked back to the patio carrying the large vase of beautifully arranged flowers, curious about the card. I opened it, read ... and suddenly sat down. It was from Mr. Mason himself, inviting me to dinner to celebrate our success in having worked so closely together.


I was impressed, having me picked up in a limousine, though he himself wasn't in it. The driver informing me that I was to be taken to his personal estate, out in the suburbs, where dinner had been arranged. It was an hours long drive, and I amused myself in having a drink, well several actually, to both calm my nerves somewhat for one thing, and for another, to show him on a more personal level, that I was perhaps indeed worthy of his attentions.

No longer working together, as far as I was concerned, there was no longer any reason to be coy or formal around him any more either. This time, if he made any sort of a pass at me, I was half a mind to receive it.

I was admittedly impressed. A half-mile long drive through the gate, eventually making its way up to the enormous looking mansion itself that sat easily on several acres. The surrounding yard, gardens, and orchard well groomed, and obviously taken care off. Pulling into the circular drive, I was let out, and escorted up a few steps to an enormous mahogany carved, doublewide set of doors. I didn't even knock as the doors almost immediately opened.

I don't know what I was expecting exactly, if I was expecting anything. But what I wasn't expecting, was to be met by a woman, perhaps a butler maybe, but certainly not someone who was dressed, and appeared to me as she did. She was absolutely beautiful, and for a moment I was actually jealous in a way. Wondering now if she was his lover, his companion, and that "they", not "he", had thus invited me to dinner and into spending the evening with them.

"Miss Mathews? Welcome, I am Deidra, one of Ted's personal assistants, welcome to his home. This way please," she said inviting me inside. And though she had addressed herself as a "personal assistant," I couldn't help wondering what else she likewise helped to assist him in, especially dressed the way she was.

Deidra was a very tall, very statuesque blonde. Her long hair full, cascading well down over her shoulders. The dress, though more gown ... flowing as she walked, hugging the curves of her obviously near perfect sculptured body. I had thought to wear one of my favorite "little black" cocktail dresses, now feeling vastly underdressed even having put that on as I followed her down the long, expensively decorated hallway.

If I had thought my own breasts to be impressive, I was even more impressed with the way hers looked. Her gown, a deep plunging "V" in front, showing off more than enough cleavage, that even I wasn't sure I'd be very comfortable with in displaying. Once again giving me pause as to her actual role and association with Mr. Mason.

I was soon led into a formal, yet cozy sitting room.

"May I fix you a drink while you're waiting?" She asked, pouring herself one obviously. "Ted will be here shortly," she added, once again waiting for my reply.

"Hmm, Ted," I thought. Certainly and suddenly less formal all of a sudden. "I'd like a vodka martini please ... dry?" She smiled at that, pouring out of a silver pitcher, obviously some had been made up ahead of time. She poured two in fact, handing one to me, the other left on the bars counter. Obviously that was Ted's preferred choice of beverage too.

It was at that moment the doors opened and Ted came strolling into the room. He had on a white dinner jacket, black bow tie, hand-tied as I could easily see, and immediately accepted the drink that Deidra now handed to him.

"Glad you could make it," he said smiling for what I believed had to have been the first time really, and then complimented me on my dress. "Please, sit down ... enjoy your drink." He then turned to Deidra. "Let us know when dinner's ready," he said simply, obviously dismissing her.

"Yes Ma..." she paused catching herself, correcting herself. "Yes Sir," she finished. She then hurriedly left, though I caught the briefest of less than satisfactory looks from Ted as she did so. His face immediately changing again however back to that near perfect smile as he held up his own drink to mine, clinking glasses.

"To a very successful and hopefully lucrative merger," he toasted. "I enjoyed working with you," he then added.

"And I ... enjoyed working with you too," I responded, now sipping my perfectly made drink.

"Dry enough?"

"Perfect," I said smiling back, fidgeting just a little as I all but melted down into the plush leather seats we were sitting in.

He stood, for the first time walking over to stand there beside me, looking down at me as he did. And it was the first time, I honestly believe, that he pointedly stared at my breasts. From his angle and position, there was no doubt he could see a hell of a lot more of me than he would have standing any place else. And I knew it, though as I'd already promised myself earlier ... if he did, I might just sit back and see what happened next.

"Besides celebrating tonight," he began once again looking into my eyes, "I wanted to invite you out here for another reason."

"Oh? And what was that?"

He smiled, that disarming, charming ... fucking good looking smile of his making me feel like some teenage girl who'd just been given her first kiss. And he hadn't even kissed me!

"I'd like to make you a proposition ... after dinner," he informed me. And then as though on cue, Deidra reappeared announcing that dinner was ready. He held out his hand to me, helping me to stand as Deidra then took our drinks, remaining where she was as I followed Ted down yet another long hallway.

Once again, I wasn't sure what to expect, or what I should have been as we were met at another large set of double doors. "Another assistant?" I asked myself as another very beautiful brunette met us at the door, dressed in the very same dress that Deidra had been wearing. She held the door open, saying nary a word, a slight bow of her head as Ted and I walked by, a small upturned smile on her lips as she and I locked eyes very briefly. Ahead of us, within an enormous room sat a small, but well laid out little table. I'd half expected some long formal dining room table as big as the room was. As though reading my mind, Ted spoke.

"I do have a much larger table, seats well over twenty guests," he informed me. But for more intimate dinner engagements, I find this feels a bit more comfortable. Looks awkward to be sitting at one end of a large table like that don't you think?"

I actually laughed. "I wouldn't know ... I'm not sure I ever have."

Ted then introduced me to "Bella," this new assistant as she in turn escorted in yet another young woman. This one less formally dressed, more like I'd expected some sort of servant, butler, or even a maid to have been dressed as she and another young woman who then appeared, brought in the first course, serving us simultaneously as Bella stood there looking on.

After Bella then poured us both wine, she followed out the two young looking females, once again closing the large doublewide doors, and backing through them as she did, almost bowing in a way.

"I can barely afford the cleaning lady I have," I said trying to make a joke, simultaneously trying to calm my nerves as I once again caught Ted with his eyes obviously devouring my chest again.

"They don't clean ... they serve," he said pointedly, though once again smiling. "I have other staff hired that do that ... but not when I have guests here of course."

"Of course," I said sipping the perfectly prepared potato soup and marveling over the obviously expensive bottle of wine that had been especially opened and served along with it.

We sat enjoying our meal together as one course after another was served. Each one perfectly prepared, especially the Beef Wellington, as we continued on getting to know one another a little better. At least far more on a personal level than we had done when we'd been alone together in the past.

When we were finished, Bella passed us back off to Deidra again, now led into yet another room where after dinner brandy's had been prepared and were waiting for us. I also noticed that there were two bound leather binders lying on a nearby table as we entered the room.

"Well, as I mentioned to you earlier, I have a proposition for you Chris, and hopefully, you'll give it some time to think about it and seriously decide."

"Decide what?" I now asked curiously, though by now ... I had a pretty good idea as to what he was about to propose to me.

"What you'd think about coming to work for me of course," he said once again smiling that smile. Such a simple thing really, and yet ... sending a pulse of excitement coursing through me, stiffening my nipples, which in turn sent a relay of anticipation and pleasure all the way down to my groin. "Now I know ... they pay you well, or well enough where you work hopefully. But after you've had a chance to read through the contracts, I think you'll find that the compensation I'm offering you, will be substantially more than that."

Now I had to ask, curious. "Two contracts? Why two?"

He paused looking at me, trying to decide perhaps if now was the time to tell me, obviously deciding that it was.

"If you're half the woman I think you are, then you've already done some homework learning about me," he began. And he was right, I had. Long before we'd even met, which is how I had learned a bit more about his lavish way of living, the bevy of women he seemed to have on each arm at nearly every social event in town.

"I have ... yes, and I'm pretty sure you've done the same thing with me as well, which is obviously how you knew I enjoyed a nice dry, vodka martini."

He smiled at that. "Yes, I have. But ... it was actually working with you, judging your character and professionalism, under stress, and under very unusual circumstances, that convinced me to see if you'd be interested in coming to work for me," he stated.

Once again, I was curious about the two different contracts however, and so asked him.

"As I've already said, I would hope that you would take both contracts home with you tonight, read both of them through thoroughly, and then after having done so, be prepared to give me an answer as to which one you'd feel most comfortable in signing." He grew serious then, his look ... the same one I'd seen him use when he was consulting, firm ... non negotiable in his approach, almost menacing. "Whichever one you decide on ... IF you decide on either one of them, is non-negotiable. I need to tell you, they'll be no discussing it, the terms are specifically clear. What it says, it says. There are no hidden or double meanings, in other words ... no fine print. It is what it is, and I'd expect you to live up to the terms of the agreement, one hundred percent. Whichever one, you decide to accept, should you choose to even do so."

Now I really was curious. "Ok, I will do that. I'll read them each thoroughly, completely, and then give you my decision. But will you at least tell me now ... what the difference between the two of them is?"

He seemed to think about that for a moment, and then nodded his head. "Very well, since you've asked, and since you've promised me to at least read through both of them later before making any final decisions towards either one, I'll tell you. The biggest difference between the two of them is this. Under the terms of the first agreement, you come to work for me solely as my assistant in whatever consulting project we're invited, or hired on to do. Nothing more, nothing less. But that means ... there will never, ever be ... anything intimate or sexual in nature between us. Period. The moment you even suggest it, hint at it, desire it ... you'll be terminated for cause."

His answer, his explanation shocking me a little. "Ok," I paused hesitating ... not sure what I should be feeling at the moment at his surprising candor by way of explaining it to me. "And the other?"

"Just the opposite," he said smiling. "You come to work for me as my assistant, much like Deidra and Bella. You'll escort me at times, be there with me to entertain and socialize with clients, friends, and influential people of all sorts in a wide variety of ways. We will no doubt become intimate, have relations, and from time to time, enjoy ourselves in the company of others. At any time you thus choose not to fulfill that particular role as outlined in the agreement, you will also be terminated for cause. And I can assure you, they're both legal, binding contractual agreements. There will be no severance, or any other monetary compensation beyond that which you will have already earned. So, as I said ... it will be entirely up to you, which one you elect to choose. But once decided, there will be no going back either way. Understood?"

He then further shocked me again. My compensation as he called it, in the first one ... the monthly amount alone more than I made in an entire year. And I honestly thought I was making fairly decent money in my position. And though I enjoyed my job, I also knew I was in a niche, one in which I would never be able to climb out of, or leave, or hope for any other kind of advancement in the company I was currently working for. It's just the way it was, family owned and controlled for the most part. And unless I was willing to marry into it myself ... which I wasn't, then I was basically at a dead-end job, even though it still paid fairly well.

But if I thought I was surprised, shocked, by the first offer, I was even more confused by the second one. It paid substantially less. Still far more than what I was making now, but at a considerable difference.

"Ok, I'm confused here," I told him honestly. "I make more ... a hell of a lot more, if there's no sexual relationship between us, just business correct?"

"In a way, yes. On paper at least. But in the second option, you will have considerably more perks so to speak. For one, you'll find there is an option to move in here, so all of your needs, requirements, and expenses will be taken care of. You'll have an entire private wing all to yourself, complete with a personal maid, driver, and even a chef, all of which will be on twenty-four hour call for you, should you ever require anything of them. Even if that is wanting or desiring a hot freshly baked cinnamon roll at three in the morning. That's what they're here for, and that's what I pay them handsomely for in doing. Obviously, you'll accompany me on certain trips, you'll be in a position to see a lot more of the world, go to exotic places with me, entertain guest with me, go to premiers ... that sort of thing. But as you will see upon reading both documents, I do have ... and will require, absolute obedience, in whatever form that it takes. If you cannot, and will not agree to either one of those conditions or terms, then we part ways here tonight. And we will not speak or see one another again afterwards. And likewise, as already mentioned. The moment you break the terms in either one of those contractual agreements, then so too will our relationship come to an immediate end. As long as you understand that, and can accept it, then either one you choose, I look forward to working with you ... or, being with you," he then added.

It wasn't long after that, I was escorted to the door again, and out to my still waiting limousine, carrying the two leather bound contracts. Both Deidra and Bella walked me out to the car, somewhat surprised that Ted had said his own good-byes for the evening there in the sitting room where we'd finished our Brandy's, not following me out.

"We do hope, you'll decide to come and stay ... and work with us," they both told me. "If you do ... I think you'll find it to be very interesting," Bella added. "If not far more enjoyable than anything you could have ever imagined," Deidra concluded. And with that, I slid into the seat, watching them close my door, and then kissing one another, as the car slowly pulled away.

"Fuck me!" I thought looking back through the window. I had every intention of reading every single word in both contracts ... at least twice, if not three times.

As it turned out, I read them both, three times that amount. And even then, I still hadn't made a decision.


I decided to sleep on it. But all I did was toss and turn half the night, getting up at four in the morning, reading them both again. What finally decided it for me, was while sitting there in the dark, all alone ... I realized then what my life had become like for me, and what it would continue to be unless I went out and did something about it.

And then suddenly, I knew.

I waited until six a.m., and then called him on his private number, which he had told me he changed once a week, so I only had that long in which to contact him with my final decision. It hadn't as yet even been twenty-four hours. To my surprise, he answered on the first ring, telling me he was in fact already up. Even the sound of his voice when he answered was sharp, crystal clear, sounding like he'd been awake for hours, maybe he had.

"Mr. Mason?"

He laughed. "For now anyway ... call me Ted. Surprised to hear from you so soon, and so early Chris," he spoke sounding genuinely surprised. "Have you made a decision yet?"

"Maybe," I responded back, though I'm not sure he was too pleased with my answer. I do have one more small question before I do that," I informed him.

Having read through the contracts numerous times, Ted had in fact been correct in that everything was clearly stated, and accurately defined. There was no legalese being used to confuse me, or require that I too obtain a lawyer, just so I could read it. And there was also no fine print. If anything, there was BOLD print, which had been paragraphed all by itself, at the bottom of one page. It was clear, precise, and obvious as to what it said. But it was also the one thing that still bothered me, caused me to hesitate.

"When asked, you will do what you're told without question."

"What does this mean precisely?" I now asked.

"Just what it says," he responded back simply. "Whatever I ask you to do, I expect you to do it, without pause, without hesitation, and without question."

Just the way he'd said that told me he meant what he'd said. The problem was, what was it he'd require of me, ask me to do? What if ... I just simply, couldn't, or wouldn't do it? I already had the answer to that, I'd be terminated, our contract broken, end of subject. But the real question was ... what would I be asked, expected to do? What if ... I just couldn't do it, was I then throwing away a good job? Would I thus come to regret my decision?"

"I know what you're thinking, what you're wondering about Chris," he told me, as though still able to read my mind. "You're concerned that I will ask you to do something that goes against your moral upbringing, your self-worth, your conscience? Yes?"

"Yes," I responded back. "That's it precisely. What if you ask me ... tell me to do something, and I can't. Then that's it right?"

"That's correct Chris ... that's it. However, let me assure you of something before you decide one way or the other. Things I might ask you to do, are things I know that you can and will do. Even during the short time I've come to know you. I believe I know you, better than you know yourself. I will never ask, nor will I ever require you to do anything illegal, or immoral, though some by society's standards might see that a bit differently. But the point is Chris, and especially in the beginning, I won't ask you to do things that I know for now ... you might not be comfortable in doing. It is not to say I won't test you a little, cause you to stretch some until you are. But I will never, ever ask you to do anything that I don't think you'd be ready or willing to do. Does that make things any easier for you?" He asked.

I had the distinct feeling he wouldn't accept another "maybe" from me ... so I told him "yes," instead.

I could almost see the smile on his face when I said that.

"Tell you what Chris, how about you come over this morning, have some breakfast with us," he said obviously including both Deidra and Bella in his invitation. "And I will give you a small, though dramatic demonstration of just exactly what I might expect of you for now. How's that sound?"

"Ok, that sounds fine," I said somewhat nervously, though excitedly too.

"You remember how to get here, or would you prefer I send a car?"

"I remember," I told him, best give me a couple of hours though before I can get there."

"You can shower here later, it's just six-thirty now. I'll expect you by eight." And with that, he hung up the phone without waiting for a response.


I barely had time enough to dress let alone anything else. I figured during the hour long drive I had ahead of me, I might at least be able to apply a little makeup. Beyond that, I threw a brush through my hair quickly, jumped into what I figured was a reasonably nice skirt and blouse, and then headed off. Taking both contracts unsigned with me when I did.

I arrived at ten minutes to eight. As before, Deidra meeting me at the door. She too looked a bit more casual, though still elegant. She had on what appeared to be an expensively tailored white blouse and black skirt. It certainly wasn't short, but she wore seamed stockings with it, and I knew then, she no doubt had garters on underneath it as well.

She smiled upon seeing me, even leaning over to give me a quick kiss on the cheek when I entered. "Nice to see you again," she offered. "I do hope you've decided to join us here."

"I don't know ... we'll see," I responded back seeing a slight look of disappointment in her face though she said nothing else, now leading me down the hall, though past the room I'd been asked to wait in before. "He's in his study this morning," she informed me, now leading me down another hallway, and then up a short flight of stairs. "This way, this is his own private quarters," she then informed me, letting me know, that coming here was by invitation only. Something I would no doubt need to remember.

He was indeed sitting behind a desk when I entered. Bella standing off to one side likewise smiling at me as I came in.

Once again another quick round of "good-mornings and hellos" followed. I placed the unsigned contracts down on his desk.

"Which would you prefer? Breakfast first? Or the small, simple demonstration first?"

I was too curious, and admittedly too anxious to wait. I'd already decided that if what I saw, or whatever it was he now asked me to do ... if I in fact couldn't do it, that there was really no point in wasting one another's time, even over breakfast.

"Why don't we do the demonstration first. That way, if we find out this just isn't going to work, we won't find ourselves being awkward over breakfast afterwards."

He smiled at that, nodding. "Deidra? Bella? If you two wouldn't mind standing next to one another at the door please?" He now asked.

The immediately did so, each one once again wearing the same identical outfits. Black skirts and expensively tailored white blouses.

Ted then looked at me, his face taking on that serious demanding expression of his. "Just remember Chris, this is only a demonstration ... a bit dramatic of course, with good reason. But even then, I don't believe I am about to ask you to do anything that I don't believe you incapable of doing. It might seem a bit of a stretch maybe, even for you. But certainly nothing that I think you, or anyone else would find themselves wrestling with after doing it. So ... having said that, shall we begin?"

Nervously I nodded my head.

"Oh, one small minor thing you need to know. When it's just us, and no one else ... you will always respond with "Yes Master." Any other time, it will be Yes Sir, or Yes Mr. Mason if we're in some sort of a formal setting, or if I am entertaining guests when you're around. Though ... there will also be what is called "relaxed time" when you are free to speak your mind, call me Ted, or whatever else you feel like calling me at the moment, without fear or repercussions for having done so. But ... to fail to do so, when it's not relaxed time, doesn't come without some form of minor penalty. All of which, either Deidra or Bella can explain to you later. So ... understood?"

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