My Boss Makes Me An Offer

Several months ago, as I was working at my desk, my boss approached me and made me a very unique offer. I was fumbling through some paperwork when he walked into my office and asked if he could talk to me. I said sure and became a little nervous as he sat down in front of my desk. He began to chat and asked if I was interested in making some extra money on the side. I told him that I was, because money was a little tight and I could certainly use a few extra bucks and asked what he had in mind. He opened up to me and said that he was having problems at home, and that he was trying to fix things with his wife. I won't get into the entire story or all the details, but basically, he knew his wife was cheating on him with her boss, and was willing to forgive her, because he didn't want to go through a divorce and end up losing his kids. As tough as it was, he would rather try to work and fix his relationship, then leave his wife. I found it kind of odd, but wasn't about to give any relationship advice because that could always backfire.

As he vented to me, he mentioned that they were going to start going out on Friday nights, to see if they could rekindle things and needed someone they could trust, to watch the kids. I wasn't crazy about the idea, until he mentioned the amount of money that he was offering me. When he told me the number, the choice was pretty easy to make. Like I said, I could use some extra cash and he was offering me plenty. All I had to do, was go to his house and watch his kids for several hours while him and his wife went out on a date. His kids were 9 and 11 and didn't really require much work, so the gig wouldn't be terribly hard. We discussed things and I agreed to help them out, especially him, because I really liked my boss. It shocked me that she was cheating on him, because he was the absolute friendliest and sweetest guy you would ever meet. He helped everyone out whenever he could, often going out of his way to do so.

After agreeing to do it, I finished up my work day and headed home. That night, I discussed the situation with my husband and he agreed with me. He was glad that I had accepted the side offer, and said that it would help out tremendously. I was relieved, because I wasn't completely sure how he would take the news.

The following Friday arrived, and after showering and getting dressed, I called an Uber and headed to my boss's house. I arrived a short time later and was taken back by the home. It was a beautiful house, and much bigger than any house I had ever been in. I made my way to the door and after ringing the bell, my boss let me in. Once inside, he introduced me to his wife and although she seemed friendly, I could tell she had a bit of an attitude.

I wished them a great night and they were soon on their way for their date, as I kicked back and hung with the kids. We spent most of the night watching TV, having some popcorn, snacks, and playing some games. It wasn't anything overly stressful and I was glad. It would be easy money. My boss and his wife arrived a few hours later, and after paying and thanking me, I was in an Uber, on my way home.

I ended up doing this same routine for the next several Fridays and was happy that I had agreed to do it. I was making plenty of extra cash and had paid a bunch of the bills at home, so things were going great. About a month or so went by and one Friday as I was wrapping up and getting ready to go, my boss offered to drive me home, instead of me waiting for an Uber. I agreed, as it would save me a couple of bucks and we were soon in his car, headed for my place.

As he drove, I asked him how things were going and he shook his head, before telling me that nothing had changed. His wife was being a stuck-up bitch and basically taking advantage of him taking her out to eat. Nothing had changed at home, and he was miserable with it. We discussed it as he continued to drive, and at one point he mentioned that he was basically at his breaking point and was considering finding someone that he could pay, just in order to get laid. He said that he hadn't had sex in close to a year and was extremely frustrated in that department.

As he talked about it, I tried to console him since I knew the feeling. Things at home weren't always the greatest, and my husband and I would go long periods without having sex as well. I understood his frustrations, but I had never considered paying someone for sex, like he was thinking about. We talked about it some more, before arriving at my house and eventually saying our goodbyes.

Things basically remained the same for the next couple of Fridays, and I continued to feel terribly bad for him. Like I said, he was the nicest guy you could ever meet, and was also very good-looking, which baffled me as to why his wife would cheat on him. I thought about his situation, and after a while began wondering if maybe we could help each other. Like I said, I was enjoying the cash and started to ask myself, if maybe, he was to offer me a little more, I could help him out with his frustrations. I knew it wasn't the greatest idea, but at the same time, I wouldn't mind getting laid, and making some money in the process. I knew it was a wild and crazy idea and one that could get me into trouble. At the same time, I also had needs because I was still relatively young, and those needs weren't being filled at home. Plus, extra cash would be a great incentive. Then again, I could be overthinking it, because I don't even know if my boss would be interested. I thought about it often, and the idea weighed on my mind for the next couple of days.

That following Friday, as I was once again getting ready to head home after their date night, I asked my boss for a ride. He agreed and we were soon in his car. As we drove, we chatted, and I mentioned that I may have a proposal for him. He asked me what was up and nervous and afraid that I might screw things up, I slowly mentioned my idea to him. He didn't say anything at first, and that made me even more nervous, but then I saw a smile creep across his face as he looked over at me and asked if I was serious. I told him that I was, and that I found him to be a very attractive person. I explained my situation at home, and after breaking everything down for him, he confessed to me as well, telling me that he found me to be a very sexy woman. We hit it off on the rest of the ride home and decided to take things slowly. He offered to take me out for dinner the following weekend and I agreed. We discussed it a bit, before arriving at my house and saying our goodbyes. I was even more nervous now, then I had been before as I realized that I had put things in motion.

The following week went by quickly, and the weekend soon arrived. I told my husband that my boss was taking me out to dinner as a thank you for everything that I had been doing, and my husband didn't seem to mind. He told me to have fun and went down to his man cave to enjoy his beer and games. I took a long hot shower, before heading into my room to get dressed. I decided on a pair of tights along with a nice shirt. Everything hugged my curves nicely, and I really liked how I looked. Once I was ready, I called an Uber and was soon on my way to the restaurant that we were going to me at. I arrived after a quick ride, and my boss was already in the restaurant, saving a table for us.

He greeted me with a hug and kiss on the cheek, while complimenting me and telling me how great I looked. I did the same, before we sat down and ordered a couple of drinks as well as some appetizers. We began to chat and while wining and dining me, he also gave me plenty of attention, flirting and complimenting me throughout the dinner. He really made it enjoyable and comfortable and it's exactly what I needed. He was treating me like a queen, and I loved it. I felt at ease and knew that we would have a wonderful evening.

Once dinner was done, we headed to the parking lot where his car was and he walked me to the passenger side door, where he opened it, and once I was inside, he closed it for me. That was something that my husband hadn't done since our early dating days, back in high school. He then got into the driver side and after a couple more compliments and thanking me for allowing him to take me to dinner, he began to drive.

As he drove, we continued to chat, and he was being very romantic. It was turning me on, as I was enjoying all the attention that he was giving me to the point where I eventually became very bold, reached over and began to rub his crotch through his pants. I couldn't believe what I was doing, but there was no turning back now.

I rubbed his crotch and could feel his cock getting hard through his pants, and by the smile on his face, I could tell that he was enjoying it. I did this for a bit before getting even bolder and unzipping his pants as he turned the car and began to drive down a dark road. After unzipping his pants, I pulled his cock out and it was at full hardness. It was about 6 inches long and reasonably thick. It wasn't super impressive, but then again, I hadn't gotten laid in quite a while, so a cock was a cock at that point.

Once I had his cock out, I began to stroke it slowly before looking around and then getting on all fours on the passenger seat. Once I was in position, I took another look around before lowering my head to his cock and taking it into my mouth as he continued to drive. I couldn't believe what I was doing. I hadn't done something like this since my college years.

I began to suck his cock and by the way he was moaning, I could tell that he was loving it. As I blew him, he reached down and began to squeeze my ass through my tights. I took my time, slowly bobbing my head up and down and it didn't take long for him to tense up. He quickly warned me that he was going to cum and I picked up my pace a bit.

I sucked him even harder and within seconds he exploded in my mouth, filling it with his hot seed. I continued to suck on his cock and used my hand to stroke it as well, pumping all his hot cum out of his cock and down my throat, and it was certainly a huge load. He wasn't kidding when he said he hadn't gotten laid in a very long time.

Once he was done, I released his cock from my mouth and sat up on my seat while smiling and asking him how it was. He looked over and told me that I was amazing while thanking me. As he did, I noticed that his cock was rock hard and couldn't believe how quick he was able to get excited again. Without hesitation, I grabbed it and slowly stroked it while looking around and telling him to find a place to park. We were in a suburban area where there weren't a lot of houses, and many places surrounded by trees, so it wasn't too hard to find a private spot to park.

After parking the car, he turned to me, and we quickly locked lips. We began to kiss each other passionately, and I was surprised that he was doing so. I had just swallowed his load and now he had his tongue down my throat. It's something that my husband refused to do whenever I had given him blow jobs. He would never kiss me afterwards, not even a peck on the lips until I had brushed my teeth. I always found it funny and didn't really mind.

As we kissed, his hands immediately went to work, rubbing and squeezing me throughout my body. He wasted no time squeezing my tits and rubbing my ass and pussy through my tights. I grabbed my shirt and took it off for him, as well as my bra, revealing my tits to his eager hands and mouth. He grabbed them and began to lick and suck my nipples while rubbing my tits all around his face. I could tell that it had certainly been a very long time since he had any kind of interaction like this. I allowed him to enjoy himself, and he did just that.

After playing with my tits for a while, I pulled my tights and panties off, leaving me completely naked in the passenger seat. I then grabbed the handle to the seat and pulled it, laying it completely down. I lied down on the seat, and he wasted no time climbing over the center console and positioning himself between my legs. I knew there was no turning back as he grabbed his hard cock and lined it up with my eager pussy.

He rubbed the tip against my opening, before plunging it deep in to me. He didn't waste any time, thrusting in and out of me, and I had expected that. I wasn't expecting any kind of romantic sex, since he hadn't gotten laid in so long. I knew that he would fuck me as hard as he could, and I didn't mind. I enjoyed a nice hard fucking every once in a while.

As he thrust, I gripped him tightly and moaned into his ears for him to fuck me harder. He did just that and I enjoyed the feel of his cock as it thrust in and out of me. It was a great feeling to be fucked again and one that I was enjoying.

He thrust in and out of me quickly and within a few minutes, moaned that he was going to cum. I gripped him even tighter and told him not to stop and that added to his excitement as he thrust in and out of me even harder for a few more seconds, before finally exploding deep inside of me. He shot wave after wave of his hot seed deep into my pussy and I loved it. I could feel him filling me with his hot cum and it added to the erotic situation.

Once he was done, he pulled out of me and climbed back into the driver seat as the two of us tried to catch our breaths. We laid for a bit before deciding to clean up and redress ourselves. Once we were done, he began driving again and took me home. He thanked me for an awesome and memorable evening and handed me an envelope. I did the same, telling him that I enjoyed our evening very much and looked forward to doing it again. With that, I headed into the house where I counted the money, and it was twice as much as I would have made watching his kids. I was happy, and since then we have gone on several more dates and even graduated from his car to hotel rooms where we fully enjoy each other and take care of each other's needs since our spouses won't do it...