My Boss's Date

  • 11 months ago
  • 17 min read
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It was another busy day at the office as I would over some paperwork when one of my coworkers stopped by my desk to talk to me. We chatted about a few different things and I made mention to her that I was possibly going to look for a second job to help me out with some of my financial problems that I was having. I had a bad habit of spending money before I made it and it had put me in quite a hole. My husband had stopped supporting my spending habits a while ago, so I was pretty much on my own when it came to paying a credit card bills. We weren't talking a couple hundred dollars either. I had managed to max out two cards and had some stuff on a third card. I needed to get everything paid off and the quicker I could do that, the better it would be. The job that I had now, paid well but I had to do something to make some extra cash. My coworker and I talked about it for a little while before she went back on her way. The following day, as I was wrapping up a few forms before lunch, my boss stopped by and asked to see me in his office before I left. I immediately became nervous and hoped that it wasn't anything bad. After finishing what I was doing, I headed down to his office and he was doing some stuff on his computer. He asked me if I had lunch yet and I told him that I was actually getting ready to go out and he offered to accompany me. I was a bit surprised because it wasn't often that he went out with his workers, but at the same time I wasn't about to deny him. He was in his late 40s and was a very wealthy and powerful man. He had invested his money when he was young, along with his father's help and since then, he had become very wealthy. On top of the wealth, he was very smart and intelligent and also had decent looks so he had just about everything going for him. After finishing up what he was doing, we headed out and he offered to drive. We walked over to his car, which was a very nice Mercedes Benz, and definitely something I could never imagine owning.

We went to a local restaurant, where we enjoyed lunch together and I was still surprised to be treated to lunch by him. As we ate, we discussed several business topics and some of the stuff that I was working on. While we were discussing things, he told me that he wanted to ask the a serious question. I wasn't really sure what to expect, and basically just sat there and told him to ask away. He mentioned that he was walking down the hall on the previous day and overheard a conversation I was having with my coworker, regarding me looking for a second job. He asked me if everything was okay and sounded concerned that I might be quitting my job. I quickly reassured him that I wasn't putting and was just trying to find a second source of income to help me with some of my finances. We discussed it for a bit and he seemed relieved that I wasn't leaving the job. He told me that if he heard of any possibilities that would help in anyway, then he would let me know. I thanked him for his help and we finished up lunch a short time later. We eventually headed back to the office where I went back to doing my work.

A few days later, as I was wrapping up for the week, I headed down the hall to the bosses office to grab my paycheck. When I walked into his office, he greeted me and asked me if I had a minute to talk. I said sure and he asked me to sit down. After locking the door to his office, he went over and sat behind his desk and said that he had a possible job offer for me to make a little extra cash. I was intrigued and asked him what it was. He began telling me that he would love to help me and hated to see me have to go out and look for a second job because it would occupy all of my free time. He said that he had a proposal for me and hoped that I wasn't offended. I just sat quietly as he continued talking and wondered what he wanted from me. As he went on, he told me that from time to time, he was invited to business dinners and other functions and whenever he went to those events, he usually hired a woman from a local agency to attend the functions with him. He said that they usually would spend several hours that evening, attending the function and then at the end of the night, they would get top sated nicely and be on their way. I was a bit taken back by his offer, as I never expected anything like that to be offered to me. It was a bit weird to have your boss asking you to basically he is date but at the same time, I would obviously be paid for doing so. He explained that it was nothing more than attending these events at pretending to be his date. He told me that he be paying the same rate that he paid the agency which some nights and that up in the women walking home with $500 or more. The amount that he was offering definitely caught my attention and I began to become more interested in his offer. It didn't sound like there was anything sexual involved, and if that was the case then I was in. I didn't mind dressing up a bit and going on some dates with him if it resulted in some serious pay. I could use the extra cash and at the same time it would make me look great in front of my boss and hopefully that would result in something good at the office. It had been a while since I had received a raise so whatever I could get would be great.

We discussed it for a while and he told me to take the weekend and think about it. I thanked him for the offer and was soon on my way home. That weekend seemed to drag on. I basically spent the entire weekend thinking about his offer, as it weighed on my shoulders heavily. I tried to look at all the pros and cons and it seemed like the money was driving my decision in a certain direction. I talked to my husband about it, but didn't go into crazy details with him. I basically told him that I would be attending business functions and that my boss was willing to pay me for attending. If I told my husband that I was his date, then he probably would be against it. After discussing it with him

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Written by Greenside 80
Cargado July 12, 2020
Notes My boss new I needed money and made me and offer...
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