Hiring Cindy

Chapter 1- Arrangements

I am in my mid thirties and single. I'm an average looking guy, but I was fortunate enough to have made a reasonable fortune in the dot-com boom. Recently I moved to Palm Springs and bought a very nice house with a pool, tons of bedrooms, etc. I had had many girlfriends in my life, some of them very attractive, but somehow something was always missing. The relationships would start out passionate, but over time the excitement would wear off and things would get more routine and less experimental. Sometimes I talked to my girlfriends about my fantasies. Sometimes they liked them, and sometimes they didn't, but even when they did like them, they never really were willing to act them out. I was looking for something different, and my mind had started to wander to a different type of arrangement.

This story starts when I was in Boston finalizing some of my affairs there. One of the last nights I was there I went out to a local bar. The bar was frequented mostly by college students, but I always enjoyed the atmosphere none the less. I was sitting at the bar when an attractive girl came up and sat next to me. I struck up a conversation with her. Her name was Cindy. She was very cute in a naive sort of way. She had light brown hair, above average breasts, a nice tight butt and a very endearing face.

As we talked I discovered that she had just graduated from the university and wasn't really sure what to do next. She was quite nervous at the prospect of finding a job. She would probably have been content to stay in Boston and continue her college lifestyle, except that most of her friends had decided to move to various cities around the country. As the conversation went on it became more apparent that she was flirting with me. The topics started to stray into sexual matters. She was single, and appeared to be relatively inexperienced. She'd had a handful of boyfriends while in school, and the most recent relationship had ended badly a few weeks earlier. The conversation drifted back to her plans for after college. Her lease expired in two weeks and she really was quite concerned about where to go when it did. She didn't have a job lined up, her parents didn't have the money to support her while she looked for a job, and her credit was maxed out.

She joked that what she really needed was to find a rich boyfriend to support her. I joked back that that shouldn't be hard for her to arrange given how attractive she was. She giggled and thanked me for the compliment, but insisted that no guy she had ever met would do that for her. I realized that this was just about the ideal chance to take a shot making my idea a reality.

Working up my courage, I said that I knew otherwise. She looked slightly startled and asked what I meant. I decided to go for it, and figured I would just come out and say it. I asked her what she would think of someone offering her a 'job' that paid up to one million dollars a year?

She said that nobody would ever offer a B student a job for even one 20th of that amount.

I said, "I am right now".

She looked stunned and confused and she asked me what I meant. I said that I would offer her up to one million dollars to live with me, and be my servant, for one year. She practically fell off of her chair in shock.

After she calmed down she asked if I were serious. I said that I was and she asked what kind of 'servant' makes a million dollars a year.

I said that she would be part maid, part secretary, part girlfriend, and part sex slave. I had never said anything like that to anyone in my life, and I was quite nervous, but she didn't seem entirely offended so I pressed on.

I waited until she composed herself, and finally she said "a million dollars is a lot of money. I would never have to worry about a job again, but a year is a very long time."

I said, "Well, it is a big decision. One that will affect the rest of your life. I wouldn't want you to make it on the spot. Here is what I propose. I live in Palm Springs now. How about if I fly you out there for the weekend next saturday. I will provide for all your expenses, pay for a hotel room for you, provide you with a limo, and anything else you require. I will also pay you $10,000 just to have dinner with me while you are out there to discuss this further. You may leave at any time and the money will be yours."

She looked stunned that someone was offering her $10,000 just to have dinner with them. How could she refuse? I got her email address and said that I would send her travel instructions, and bade her goodnight.

The next morning I made the travel plans and emailed them to her. I told her to be at the airport at 9am on saturday, and that the limo driver would meet her at the airport in Palm Springs and take her to the hotel. She was to be ready to come by my house for dinner at 7pm. I also decided to test her willingness a bit. I instructed her to wear a cute dress, matching sexy bra and panties, and high heels. I figured there was only about a 20% chance that she would show up, but I had nothing to lose, so I made the arrangements. To my surprise, the limo driver called me up on saturday after dropping her at the hotel to tell me that she had arrived and would be at my house at 7:30. I was going crazy with anticipation...

Just before 7:30 I heard the limo pull into the driveway. I went outside to meet her. I was pleased with what I saw when I opened the door. She gave every appearance of trying to impress me. Her makeup and hair were done impeccably. She was wearing a classic 'little black dress' that stopped well above her knees. She was wearing black stockings and black high heels. As she got out of the car I was impressed to notice a glimpse of the top of her stockings. That they were not actual pantyhose seemed to hint that she realized she might be asked to take off her dress.

After she got out, I instructed the driver to wait right there, and take her back to the hotel or wherever she requested, whenever she asked. Then I took an envelope out of my pocket with a cashier's check for $10,000 in it. I laid in on the back seat and told her that if she wanted, she was welcome to leave immediately with the check, but that would be the end of our arrangement of course.

She looked surprised and said that of course she would prefer to have dinner with me, so I lead her inside and sat her in front of the fire on the couch. I thanked her for coming.

She said that she was very curious what exactly I was proposing.

said, "ok, right to business then." and pulled out the contract I had prepared. I gave it to her to read. After some legalese it said the following:

#1) I would set up a bank account in solely her name in a Swiss bank. She would have all the information required to verify the balance and nature of the account at any time. Each month, on the last day, I would deposit $20,000 into the account. It would be tax free and anonymous.

#2) I would place an additional $20,000 into that account on the first day of our arrangement.

#3) At the end of the year, I would deposit $680,000 in that same account.

#4) I had set aside $60,000 for bonuses which I would offer throughout the year.

#5) Either of us may call this entire arrangement off at any time. She could call it off without having to give any explanation at all. I would only call it off for one of two reasons- if she failed to follow an instruction or if she did not convey the appropriate attitude. If I ended the relationship after more than 1 month had passed, I would deposit an additional $50,000 into her account. Whenever the agreement was terminated by one of us, she could keep all of the money received so far, but would not be entitled to the 'end of year' payment.

#6) During her term of employment, she would serve me in any role I required. This would include maid services, secretarial services, playing my girlfriend, and playing my sex slave. She would follow any instruction promptly and without complaint. Unless otherwise instructed, she was always to appear enthusiastic, loving, and happy.

#7) I may ask her to do things that she has never done before, or is uncomfortable with. For example, she may be asked to have sex with me, sex with other men or sex with women. She may be asked to wear extremely revealing outfits in public. She may be tied up. She may be spanked, but would not be submitted to extreme S&M or humiliation. I am interested in making this experience as enjoyable as possible for her, but the primary purpose of this contract is to ensure my enjoyment, so she would definitely need to perform some duties that went beyond her normal comfort level. I would, however, ask her to provide a list before we began listing those types of activity which would make her quit the arrangement. I warned her, however, that I would need to see that list before signing the agreement, so she should think long and hard about how far she was willing to go.

#8) She would work for me 24 hours a day, 7 days a week, with the exception of the last sunday of every month, when she would be free to go and do as she pleases, with the sole exception that she was not, under any circumstances to date or hook up with a man during those days.

#9) She was never allowed to masturbate or be intimate with anyone without my permission.

She sat deep in thought after reading the contract. She was clearly apprehensive.

She said that she didn't know if she could keep something like this up 24 hours a day, every day.

I said that that was an understandable concern, and that at times it would certainly be tiring for her, but that at the same time, it wasn't my intention to have her playing the sex slave role at all times. I expected that she would spend a fair amount of time cleaning and cooking, a fair amount of time reading in her room or lounging by the pool. I said that I didn't have the energy to play this game constantly either. I also said that it was my plan to start this out slowly, and reminded her that she could quit after a day if she were uncomfortable, and she would be $20,000 richer for her time.

She seemed consoled by that point, but asked if she needed to decide right then.

I said "no, let me show you the house first and have dinner".

I took her on a tour of the house. I showed her the pool, the various living rooms, my bedroom, and her room. Her room was really a large suite of rooms with a nice bathroom, a good sized bed, a huge walk-in closet, and all of the luxuries one could desire. She was clearly impressed by the house and excited by the idea of living in such luxury for a year. After the tour was sat down at the dinner table and I brought in the food. I told her that that was probably the only time I would be serving her dinner and we laughed. We talked during dinner, and really continued to hit it off. She was smart and funny, and gave every sign of enjoying my company.

After desert I asked her if she wanted to leave, or if she would be interested in continuing the 'interview'. She said that she wasn't sure yet whether I would accept all the things she wasn't comfortable doing, but she wanted to keep talking about it.

I said, "great" and said that we should get to her list in that case. I reminded her that there was a lot of money on the table, so if she was serious she should be very careful of how many things she put on the list of things she will not do. I brought her into the study and gave her a piece of paper, and left her to think things through.

When I came back, she presented me with the list. She had written that she would quit if she were asked to do a predictable list of things like scat play, serious S&M, anything that would get her arrested, etc. There was only one item on the list that I didn't like. She said that she would not have sex, or even touch, any strangers.

I told her that I didn't know how far I would want to take it in reality, but that I definitely had fantasies about asking her to touch, be touched by, and have sex with strangers. I said that if she were firm about that rule I would not accept the arrangement. She looked very distressed, so I offered her a compromise. I would not ask her to touch or be touched by anyone other than myself, for the first 3 months at least. At that point, we could discuss it again. If she still felt strongly about that point, she could leave with a good chunk of money.

She said that that sounded reasonable to her.

Then I said that I wanted to see what I was getting for my money, and I asked her to stand up and take off her dress. She looked uncomfortable, so I reminded her that she could leave at any time. She looked like she was considering it, but ultimately she stood up facing me and nervously unzipped the back of her dress. She let the dress fall off of her shoulders and then down to the ground and she stepped out of it. She looked stunning. She had on a matching, small, black pair of panties and bra, her thigh-high stockings, and a pair of high heels. I was very pleased and started to get excited. She looked uncomfortable, but didn't cover herself. I asked her to turn around. She complied nervously, and I was satisfied to see that she had a great ass that was barely covered by the thong back of her panties.

I said that she was very beautiful, and that she could put her dress back on. She quickly complied, and I said that I was satisfied with both her list, and her beauty. I asked how she felt about the arrangement.

She said that she was very interested, but she wanted more time to think about it.

I said that that was fine with me, and suggested that if we were to do this she should be at the airport in Boston, with the signed agreement, one week from that day. I instructed her that she should wear something cute, but bring only a small bag with personal items. I told her that there was no need to bring any clothes, and that I would be providing her with a whole new wardrobe. I took down her size and measurements and walked her back out to the limo. I held the door open for her, and she said that whatever else happened, she had enjoyed having dinner with me, and she gave me a quick kiss on the lips before getting into the car.

I was not certain that she would come, and we didn't talk at all during the intervening week, but I spent my time preparing just in case. I bought her dozens of dresses, pairs of underwear, stockings, swimsuits, costumes, night gowns, and everything else I could think of. It ranged from cute to absolutely over the top sexy. I put it all in her closet and waited.