Rob's Fortune

I smiled and said, "Luckiest accident I've ever been involved with."

When we arrived we were each given a ticket for the drawing that would determine who would get the signed first editions that were being given away and my number was called. On the drive to the event Ellen and I had discussed the dinner and the circumstances and I learned that the author was one of her favorites so I took Ellen's ticket and gave her mine and sent her up to get the book. The author personalized the inscription and Ellen thanked me and asked why I didn't want the book for myself. I lied and told her that as a member of the committee I didn't feel that it would be right for me to take the book. The truth was that I had read two of his other books and hadn't liked either one of them.

After the dinner I asked Ellen if she would like to stop somewhere and have a drink or two with me and she said yes. I'd expected that she would since we both knew that she was on my time for another two hours. We stopped at Sardi's and when Giselle came to take our order Ellen asked for a Cosmo and I asked for my usual. My usual looked like a vodka tonic with a slice of lime, but was actually a glass of water with a slice of lime in it. I made it a habit not to drink and drive, but I had found that just ordering a Coke when everyone else was drinking made some people uncomfortable. It was almost as if they thought something was wrong with me if I didn't booze it up.

As soon as the drinks arrived I started asking Ellen about being an escort. Not the "what's a nice girl like you" type of questions, but questions about what an escort could do. She was hesitant to answer and I thought maybe she was thinking I was trying to sound her out on whether or not she played for pay so I figured that I'd better explain.

"What I want to find out is if a long term relationship is possible. By that I mean can I arrange to have the same escort all the time or do I have to take pot luck every time I contact the agency for a date?"

"It depends."

"On what?"

"Say you wanted the girl for every Thursday or every Saturday. Yes, you could lock her in for those specific times or at least you could as long as she still worked there. But if you were to call on a Tuesday and ask for a specific girl for Thursday it would depend on whether or not she was already booked for that night. Why do you ask?"

"Because I can see the need for me to have to use escorts on a regular basis and showing up with a different woman every time I attended an event would make me look a little unstable and that is an impression that I don't want to make."

"How far ahead of time would you normally know if you needed someone?"

"Usually a week or two, but sometimes only a day or two."

"A week would probably give you enough time to insure that you get the woman you want, but a day or two would be iffy."

"Could I ask a woman for a date at the end of the date and have her inform the agency or do I always need to go to the agency?"

"You need to go to the agency because she could already be scheduled for something else and not yet know it."

We talked a little more and then I drove her back to the agency so she could pick up her car.

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My life settled into a pattern. Work, evening classes at the college taking the classes that I had wanted to take back when I was earning my degree but couldn't and attending functions put on by the committees I served on. I dated off and on, but never found anyone that I was interested in.

I did have a sex life of sorts. A friend had put me in touch with an extremely high class call girl and once a week for fifteen hundred I was able to take care of my needs. Tasha was so good that once I even offered to set her up as a full time mistress, but she told me no. She was another Marcy, but at least she was honest about it.

"I'm curious about different cocks and I'd have to give that up if I settled in with one man."

I called the agency and asked for Ellen several times and always had a good time when she was with me. Twice she wasn't available and one time I got Mellisa and the other time I got Karen and while they were okay I didn't enjoy myself as much with them as I did with Ellen. I found myself thinking of Ellen a lot. She seemed to be everything that a man would want in a woman and I couldn't understand why she wasn't engaged or married. Or maybe she was and didn't wear her rings, but I didn't think it likely. Even though we did spend a lot of time together the relationship wasn't the kind that let me ask her about her personal life.

Then I hit a rough spell as far as escorts go. Four times I needed an escort and Ellen wasn't available. The ones I ended up with served the purpose, but I was less than satisfied.

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The fall semester rolled around and one of the classes that I wanted to take was only offered in the afternoon on Monday and Thursday. One of the nice things about being the boss was that I could give myself time off from work during the day and so I signed up for the class.

The second day of class I got to the campus early and so I decided to go to the cafeteria in the Student Union for pie and coffee. After I paid the cashier I looked around the room looking for a place to sit and I saw Ellen sitting at a table alone with her nose in a book. She looked up annoyed when someone sat down uninvited on the chair opposite her and when she saw it was me she smiled and said:

"What are you doing here?"

"I'm a little early for my two o'clock so I came in here and I saw you over here so I came to join you. I can leave if I'm interrupting something."

"No,no, I was just reading up on what Professor Reynolds will be covering today. I didn't know that you were a student here."

"Then we have something in common because I didn't know you were either."

We talked and I found out that she was working on a degree in Business Management and had been working on it for three years and hoped to be done with it in another three."

"Why so long?"

"Money and time. I have to keep the days free for classes so I have to work nights. But I can't work a full time night job because I do need time to study and work on term papers and the like. Escorting pays pretty good when you are working, but it is tight trying to squeeze living expenses and schooling out of what I make. Sometimes I can only afford one or two classes a term and that is why it is taking me so long."

"What do you mean "pays pretty good sometimes?"

"You have to go on dates to make money. Some weeks are good and I get called three or four nights and some weeks I only get one. There have even been weeks when I never got a call at all so I have to budget pretty close."

I looked at my watch and saw that it was time to head to class. I told Ellen I would talk to her later and I got up and headed for class. On the way home I came up with a germ of an idea and by the time I got to work the next morning the germ had grown. I called Premier and requested Ellen for the Tuesday of the coming week. They said she was available for that day and I told them to tell her to dress casual – jeans would be fine – and to have her meet me at the Texas Steakhouse on Bromley Lane.

I was there in a booth when Ellen arrived and when she sat down she asked me what we would be doing and I said that we would be having a business meeting.

"A business meeting? Dressed in jeans? And why in the world would you want me in a business meeting?"

"You are a business major right? And you have specific knowledge that will be pertinent to the discussion."

"What knowledge?"

"Your knowledge of the escort business."

"I don't understand."

"It will all become clear to you at the meeting, but right now enjoy your dinner."

Over dinner we talked about school and I told her why I was taking classes and she told me that she knew just where I was coming from. She had classes that she would have loved to take, but they wouldn't help her get to her degree. We followed dinner with some Bailey's Irish Cream and then I said:

"Okay, time to talk business."

"Where is the meeting?"

"Right here."

"I don't understand."

"On our first date I told you how important it would be to me to have the same woman as an escort whenever I needed one. It has worked out for me some of the time, but there have been several times when I have called the agency and you haven't been available. Last Thursday in the cafeteria you filled me in on how unpredictable the escort business is as far as employment goes and how you have to budget real tight so the good weeks will offset the bad ones. I've thought about it and I've decided to offer you a proposition."

"Whoa! I don't think I want to go there."

"You haven't heard the proposition yet so don't go jumping the gun. On our dates I have never even hinted, not once, at doing what just flashed through your mind. Not that I haven't thought about it. Here's the deal. I want the same woman with me when I attend social functions and I do not want to play hit or miss when I call the agency. I want to hire you as a full time escort – a full time employee. I will hire you through my company so as a full time employee you will be entitled to most of the benefits like health insurance, paid vacation, 401k, sick leave and stuff like that. You will also get some of the paid holidays, but not necessarily all of them because on some of them you will have to be with me at some function or other. Does that sound like something that you might be interested in?"

"It sounds intriguing at least as far as benefit go, but what about pay?"

"What did you make last year?"

"Well, that's the sticking point."

"Why?"

"There is what Premier paid me and what I made under the table."

"My turn not to want to go there. Just give me the total of what you made last year."

"My income from Premier was just a little over thirty-nine thousand."

"And the under the table you mentioned?"

"I'm going to be honest with you Rob and I hope it doesn't change your opinion of me too much, but I made another thirty under the table providing additional personal services."

"Additional personal services?"

"Some clients wanted a little more than just someone hanging on their arm for the evening."

It took a second for what she said to register. "Oh. Oh my. How come I never knew that?"

"Because I only do it if the client asks and even then not always. I never volunteer the information."

I looked at her for several seconds and then said, "That doesn't change anything. The offer is still on the table. All we need to do is work out the details."

"You are willing to pay me seventy thousand a year just to be your permanent arm candy?"

"No. I am willing to pay you forty and carry you on my books as my personal assistant."

"I appreciate the offer Rob, but I can't do it."

"Why not?"

"The money. Discounting the under the table income which is not all that reliable since it depends on the client asking and a lot of clients like you never ask, my after tax income was only about twenty-nine five. When I get done paying rent, utilities, car payment, car insurance, groceries and keeping myself in the kind of clothing I need for the work I do I'm pretty tapped out. My under the table is what pays for school and as I've just said it isn't all that reliable."

"What I'm hearing is that you would consider it if the money was better."

"Of course I would. It would give my life some structure. I wouldn't be waiting around for the phone to ring to tell me that I had work that night or the next and knowing that I had a steady paycheck would be a relief, but what you are offering just won't do it for me. Without the escorting I wouldn't have the under the table opportunities and it is that money that is paying for my schooling and earning that degree is what is going to lead me to a decent job where I can show my worth, climb the corporate ladder and end up in a position paying me a pretty decent to a very good salary."

I looked at her as I contemplated what she'd said and then I said, "Forty is as high as I can go on wages without having to make some awkward explanations, but there are some other things I can do. How much do you value the privacy that living alone gives you?"

"What kind of a question is that?"

"I need to know if you would be willing to give some of it up if the circumstances were right."

"I don't know."

"I'm going to lay this out and I want you to spend some time thinking about it. I have a six bedroom house in Regency Park. I've turned one of the bedrooms into a home office and den. You can have one of the other bedrooms and I'll convert the one next to it into a study for you. That will eliminate your apartment rent and utility costs. I'll give you a company car and a company credit card to pay for gas and you can sell your car. That will get rid of the car payment and the insurance costs. As far as school is concerned I'll pick up tuition and books. Since most of the time I am going to want you on my arm is in the evening you will have pretty much all day to take classes and that means that you can start carrying a full load instead of just a couple of classes a semester. Take some time to think about it. I'll call the agency and set us up for Saturday evening and we can talk about it some more."

I could see that she had a lot of questions, but I did not want to deal with them until she'd had time to thoroughly think about my offer. As I drove away from the steakhouse I was asking myself if I knew what I was doing and I had to honestly admit that I didn't. Did it even remotely make sense? I used escorts maybe four times a month at an average cost of about four hundred dollars. That was sixteen hundred a month or nineteen thousand two hundred a year. Why was I offering two and a half times that much just to guarantee having the same girl every time I needed one? I was single. So what if I showed up with a different woman every time I went somewhere? Then I started thinking that I was going to have to come up with some sort of reasonable explanation for the people at work if I did end up putting her on the payroll. I fell asleep still wondering why I had done what I'd done.

By the time I met with Ellen on Saturday I'd thought the idea to death and the best I could come up with was that I really enjoyed being with Ellen and I liked being seen with her because she was drop dead gorgeous and being seen with a drop dead gorgeous woman hanging on me didn't hurt my reputation at all. As for financial justification? What the fuck! I could afford it and I didn't have to justify it to anyone.

And there was one more thing. One more very important thing. It took a while before I admitted it to myself, especially after all of my previous experiences, but I wanted Ellen. I wanted her, but knew that I couldn't have her, at least not in the way I wanted. She would never be interested in someone my age and while I couldn't have her I could have her close. I could have her in one way because she had told me herself that she had provided "extra services" for some clients, but I didn't want to go there. It would change the relationship in ways I might not like so I would stay with Tasha to take care of my needs in that area.

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"So, what did you think about my offer?" I asked Ellen over the table at the restaurant.

"I like it because it would allow me to concentrate on school, but I have some reservations."

"And they are?"

"Two really big ones. First, I give up the apartment, say goodbye to the agency and a month later you change your mind. There will be no apartment, no job, carrying a full load at school that I will have to drop so I can use the time to find a job. Next is the privacy issue. I don't have a boyfriend now, but if and when I come up with on how would we handle my bringing him home?"

The thought of Ellen with a boyfriend didn't set well with me at all, but I should have expected that it might come into the mix at some time. I would just have to put it out of my mind.

"To allay your first concern I'll give you a legally enforceable contract and it will have a renewable clause and financial penalties for early termination. I'll make it for two years. That will give you enough time to finish school and then figure out what you are going to want to do with your degree. Taking a full load you will probably finish in a year or a year and a half and two years will give you some cushion. At the end of two years we can discuss renewal. As for your second concern I don't see a problem. The company has an account with Best Western and I will add your name to the list of those people authorized to use the account. If you feel awkward about bringing him home with you you can use the Best Western. What else?"

"What do I tell my mother?"

"That is strictly up to you. Tell her whatever you like. Just let me know so that if it ever comes to it I can back you up. Maybe tell her I hired you to house sit because I travel a lot on business."

By the end of the evening she decided to do it and on Monday she gave notice at the agency and informed her landlord that she would not be renewing at the end of the month. Two weeks later on a Wednesday I helped her move her things into the house at Regency Park.

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Thursday morning I had to question my sanity in making the deal I had with Ellen. I got up at my normal five am to do my morning workout on the equipment I had set up in my basement. When I got there I found that Ellen was already up and was working out on the Stairmaster. She had on a very short pair of shorts and she was obviously not wearing a bra under her tank top. Instant wood! Instant obvious wood! To keep Ellen from noticing I made sure that I did my workout with my back to her.

And that was just the start of it.

It seemed that her favorite sleeping outfit was an oversized tee shirt and she thought nothing about moving around the house in the morning in just it and most of the time without a bra under it.

What really did me in was what happened when I told her I was a member of the country club and I had put her name on the list as a member of my family. One Saturday around noon she came out of her room in what she laughingly called a bikini, but was no more that three very small triangular pieces of cloth held together by a few pieces of string and told me she was going to the clubhouse, lay by the pool and soak up some sunshine. Luckily I was wearing baggy sweats at the time so she couldn't see the effect that it had on me. I pointed at the scraps of cloth and said:

"In that?"

"Sure. Any thing wrong with it?"

"Only that you are going to give some of those old farts over there heart attacks. I hope nobody drowns because the lifeguard won't be paying any attention to anything but you."

"You say the sweetest things."

She turned and walked to the door and I saw that marvelous ass with the tiny string running between her butt cheeks and I'm amazed that I didn't faint because of all the blood that rushed to my cock to turn it into an iron bar that I could have driven nails with.

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Two months went by and I used Ellen on the average of two times a week and I usually took her out to dinner on either Saturday or Sunday. She seemed to be very comfortable with our arrangement and there was no awkwardness in the house. She gave me a lot of 'wood' but I managed to hide it from her although I did increase my visits to Tasha.

The only problem that I had was with my accountant who told me that I couldn't (or at least shouldn't) be doing what I was doing through the company books. I finally had to tell him to do it and then do whatever he had to do to make it legal. If I had to pay some extra taxes or whatever, just get it done. "What the hell" I hollered at him, "It is my goddamned money and I'll do with it what I want."