My Boss's Date
- 9 months ago
- 17 min read
- 94,795 views
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 and thinking about it some more, I decided to give it a shot. I really needed the cash and at the same time I really wanted to make myself look good in front of the boss. The following Monday arrived, and after going to work, I stopped and talked to my boss and told him what I had decided. He seemed happy and said that he would prefer to give the money to somebody that he knew really needed as opposed to one of the girls at the agency. We discussed a few things and he told me that he would let me know when the first get-together would be. I thanked him again and was on my way back to my office to do my work.
A few days went by before Adam, my boss approached me. He told me that there was a function coming up and wanted to see if I was ready to attend. I smiled and told him that I would be honored and he gave me the date along with the details. I was excited but at the same time I was nervous, as I didn't know what to expect. I would be attending a business dinner with him the following Saturday and hopefully I would do a great job.
Saturday arrived and I was a nervous wreck as I began to get ready. I decided to wear a nice dress that wasn't overly sexy, but enough to get the point across. It hugged my curves and showed a slight touch of cleavage. It wasn't anything crazy I wasn't showing off too much but at the same time, I really liked how I looked. After getting ready, I went into the living room to wait for my ride. Luckily, my husband was down the basement in his man cave and didn't really notice that I was leaving. A limo arrived a short time later and I was impressed as I headed out. Adam was already inside and greeted me as I got in. He complimented me on my looks and thanked me for attending. After a short drive, we arrived in the city at a very elegant restaurant. I spent the rest of that evening by Adams side, pretending to be his date while he discussed business stuff with other business owners. We ate and drank very expensive wine and overall the experience was very nice. As the evening came to an end, I am thanked me for being such a great sport and for doing such a great job as his date. I was grateful and thank him for giving me the opportunity. He handed me an envelope and told I have a great evening as the limo dropped me off at my home. Once inside my house, I opened the envelope and saw five $100 bills. I smiled and thought to myself, this wasn't so bad. From there, I attended several more business functions with him over the course of the next couple of months. Each time, it was a similar situation where I was pretend to be his date at the end of the night, I would get compensated very nicely for all and all, I was making a decent amount of cash and Adam seemed to be happy with me as his date.
Things were going good and I was doing good at work as well. After six months of attending these events with my boss, he mentioned that there would be a few promotions coming up and that I was in the running for one of them. I was excited because a promotion meant more money, which would help me out in a great way. I thanked him repeatedly and told him that whatever he was willing to do would be great and highly appreciated.
As the week of the promotions approached, I grew nervous and tried to do my best at work so that I could impress everyone. My boss mentioned that there was a big event that Saturday, where a few of the higher ups would be attending and discussing promotions throughout the entire company, in all of the branches. He told me that the main executives from the branches upstate would be in attendance and that this was a very big get together. He even offered to pay me extra in order for me to the extra friendly that night and just put on a heck of a performance so that he looked good as well. I told him it wasn't a problem and figured that I would just to a few extra things like holding his hands and hugging and kissing him on the cheek and whatnot. It really wasn't a big deal for me. I just needed that promotion.
Saturday arrived and I once again got ready for the big event. I went with a nice black dress that hugged my curves and showed off a decent amount of cleavage. I usually only wore this dress when my husband and I went out special occasions. It turned him on to watch me walking around in it so hopefully I would be able to turn some heads and impress at this event. After I finished getting ready, I headed out to the limo that was already waiting for me. Adam was inside and was wearing a tuxedo. We quickly complimented each other as the limo began driving us to our destination. We arrived in the big city and attended the gala at a very fine dining establishment. As the night went on, I did my best to impress everyone. I constantly held Adams hand and the close to him whenever we mingled with people. There was music playing and I made sure to hold him close as we danced. I even rested my head on his shoulders and made it look like I was kissing his neck while we danced. It actually was a very nice feeling and I was enjoying myself. Even though I was acting, it felt nice to do. Throughout the night, we would flirt and complement each other and on a few occasions, we playfully gave each other pecks on the lips. I was having fun and Adam seems to be enjoying everything that I was doing which indicated that I was doing a great job. Everybody that was talking to us also seemed to be very friendly and were enjoying our company so in the end, I assumed I was doing everything that I was supposed to. I enjoy the night and had a great time.
As we were wrapping up, we said our goodbyes to everyone and began to get ready to leave. As we headed out to the parking lot to wait for our limo to come around, Adam turned to me and thanked me for everything I had done that evening. He said that everything was going good and that I was definitely in line for the promotion. He told me that he had an incredible evening and really enjoyed my company and I thanked him while telling him that I had a great evening as well. The limo pulled up and we got inside. Once we were inside, he handed me an envelope and told her that he had compensated me well for everything that I had done that night. It was more than what I usually got and I was very grateful. As we talked about it, he once again thanked me for all the fun that he had and asked if I was interested in other proposal. I asked them what was and he said a little closer to me on the seat while looking me in the eyes. He said that after a night like that, he wouldn't mind compensating me a bit more if I were interested in extending the evening. I pretty much knew what he meant and before I could answer, he leaned in and kissed me. I responded by kissing him back. I guess I was caught up in the moment as the two of us locked lips and kissed each other pretty passionately. We kissed for about a minute or so and after breaking the kiss, he grabbed the phone and notified the driver to go back to his condo. I surprisingly didn't disagree or offer any resistance and we ended up kissing each other for the rest of the ride to his condo.
After arriving at his condo, we headed inside and I immediately noticed how nice of a place it was. He gave me a tour and I noticed the king-size bed, along with the hot tub. I was extremely impressed as we made our way to the living room where he poured us each a glass of wine. We sat on his huge couch and sipped the wine while chatting with one another. After finishing the wine, he stood up and took me by the hand, leading me to his bedroom. We immediately began kissing each other and it wasn't long before I felt his hands roaming around my body. He paid special attention to all of my curves, rubbing and squeezing them before slowly pulling on zipper of my dress. Little by little, he undressed me, leaving me standing naked in front of him. As he admired my body, he began to undress himself and I noticed his hard on. It was reasonably impressive, probably around 7 inches long and fairly thick. I could feel excitement growing within me as I looked at his cock. Once he was undressed, he once again turned his attention to me. He began to kiss my body all over, and paid special attention to my tits, licking and sucking on my nipples while squeezing them. I enjoy the feeling and it wasn't long before he had me lie on his bed.
After lying on the bed, he climbed on top of me and continued to kiss my body. He worked his way down to my pussy and spent a few minutes licking and sucking on my clit. It drove me wild as I laid back and gripped the sides of the bed. I couldn't believe how amazing it felt to have his tongue working my pussy. My husband didn't eat me out very often so this was a nice change of pace. It didn't take him long to work his tongue in and out of me before he sent me over the edge. I let out a loud moan and thrust my hips upwards as I began to cum. I couldn't believe that it was that easy. I came very hard and it sent shivers through my body as waves of ecstasy rushed through me.
After making me cum, he worked his way back up to my tits and as he did, I could feel his hard cock rubbing against my pussy. It wasn't long before he guided the tip of his cock to my opening. He easily penetrated me, burying his cock inside of me as I let out a loud moan. This was the first time I had another man's cock inside of me and it felt great. He was bigger than my husband and definitely thicker. I quickly wrapped my arms around him as well as my legs as he began to slowly thrust. He took his time, fucking me slowly and the two of us really enjoyed what was happening. As wrong as all of this was, it felt amazing and erotic to be fucked like this. There was just something about it that I couldn't explain, but it was mesmerizing and erotic. I hadn't felt this horny in a very long time.
Little by little he increased his pace and began to fuck me harder and harder. It felt great and I began to moan louder and louder with each thrust. It wasn't long before he tensed up and exploded inside of me, flooding my pussy with his hot cum. He continued to thrust as he emptied his balls inside of me. He thrusted until he was done, before finally pulling out of me. He then collapsed by my side as the two of us laid in a sweaty heap while trying to catch our breaths. We laid for a little while before starting to flow around again. We ended up spending the next several hours fucking each other and had one hell of a night. He gave me a fucking session like I had never experienced in my life. It was erotic and enjoyable and I had one hell of an experience.
Like he had promised, he compensated me well and I almost felt that taking his money because I had enjoyed the sex just as much as he had. I continued to attend functions with him and everything worked out positively for me. I got the promotion and was making twice the amount of money that I had been earning previously. My husband was happy because I was finally getting out of debt and he had no idea how I was making so much money. I continued to have fun with Adam at our work related events and we even started having some fun in the office after hours. Those however are stories for another time…