This story is bittersweet. I’ve mentioned my ex in a story before, specifically how he started to training me to be his little anal slut. (Link). But there’s a lot more to our relationship. It started in a pretty fucked up way, though I didn’t quite see it at the time. Well, you can guess, it also ended in a pretty fucked up way. It was never perfect, but there were some very fun, and some very sexy times over the course of about three years. Ultimately, he turned out to be a piece of shit.

I was in another failing relationship. My ex, Ben, and I were merely coexisting in the same apartment. Any romance or spark gone. I should have ended it already, but I was scared to hurt him. And of course, knowing me, I was suffering from wandering eyes. Yes I know it’s bad. Yes, I’ve tried to work on myself since then. But at the time, it was what is what.

I worked for a small company. I worked in our HQ office, but many members of our company mostly worked remotely from various cities around the country. Once or twice a year everyone got together for a team meeting or conference. I hadn’t been at the company too long - so this was my first time meeting some of my coworkers who I had only interacted with online.

We socialized a bit in our HQ office at happy hours, but nothing ever got too crazy; so, I didn't expect the team meeting to be too thrilling. During the first day we all sat through 8 hours straight of meetings, so I think everyone was definitely ready to unwind in the evening. After dinner my coworker, Ben, knew the city we were in well and lead a group of us to a few bars in the area. We started taking shots at every bar we went to, and I was getting progressively more drunk.

When I had met him earlier in the day, Ben didn't specifically stick out to me, but I was also just meeting everyone for the first time and not going into things with a flirty mindset. He was pretty quiet all day, so I didn’t have much of an impression of him yet. As the night went on our conversation picked up a little bit of a flirtatious vibe and he seemed quite funny, and very confident. He had a very irreverent sense of humor. Pushing the envelope of things you’d say around your colleagues. Maybe even a little cocky. I found myself drawn to his energy.  

At the last bar we went to, a group of about 7 or 8 of us had to squeeze into a booth really made for 5 or 6. Ben and I were sitting next to each other. My leg was pressed up against his, and I realized I really liked the feel of it. A bad realization was dawning on me. I was very turned on by him. He was suddenly so sexy. I noticed his handsome facial features, toned arms, big hands. I could tell he was tuned into me. Watching me with interest whenever I’d speak to the group. I knew: if interest was mutual, there was no way to stop myself from sleeping with him at this point. I had accidentally let myself pass the precipice of self control.

I tried not to make anything obvious as of course I didn't want to come across as unprofessional around my other coworkers. 

We all decided to take a taxi back to the hotel, and Ben and I were both sitting in the very back of an SUV. For a moment he put his hand on my thigh and gave it a little squeeze. He had confirmed that the interest was mutual. Sleeping together was truly inevitable. I thought it was incredibly sexy that he was bold enough to touch me in the uber we were in with all our other coworkers, and confident enough to even make a move in the first place. Pretty sure I had mentioned having a boyfriend more then once over the course of the night. A group of us went back to his hotel room, and slowly people left one by one. As the last person left I acted like I was about to leave as well, but let them go a second earlier.

But then, when we were alone I crossed from the other side of the room and went over and sat on his bed. There were a few moments of heavy silence. Then he walked over to me, looked me in the eyes, leaned down and kissed me.

From there a mad rush to take off our clothes insued. There wasn't a moment wasted before we were tangled together naked and making out. I broke the kiss and said "Don't you have a girlfriend?" to which he replied "...Don't you have a boyfriend?" We both said nothing and went back to furiously making out. He kept calling me sexy and hot and beautiful and was exploring my entire body with his hands. His hands were really big and strong and I loved feeling them all over me. 

He kissed down my body and proceeded to give me some of the best oral sex I have ever received. He had a couple of fingers inside me as he expertly used his tongue to play with my clit. He had me cumming in no time. After I came he moved back up and started to rub his hard cock all over my clit and my opening, without entering me. It drove me crazy and I told him I had to feel him inside of me. Finally he relented, and slid his hard cock inside of me, commenting on the fact that I was dripping wet.

He was incredibly strong with muscular arms and a firm torso and he used literally every ounce of force to fuck me hard. He just kept going and going. He flipped me over and started fucking me from behind with his hands all over my ass. I had probably cum one or two more times by this point.

We stopped and took a break, and then picked back up again, over and over for the next few hours. I have not had sex like this with my boyfriend in so long. Ben and I would fuck until we were exhausted, but as we laid next to eachother our hands would start to wander and suddenly he was pushing himself inside of me again. Incredibly, at this point - a few hours from when we started - he hadn't cum yet even though I had cum so many times already.

When we were taking one of our breaks - probably around 5 AM at this point - I whispered in his ear that it was his turn to cum. He forcefully pulled me toward him and slipped himself inside of my soaking pussy. I wrapped my arms and legs entirely around his body as he pounded me hard. It felt like he kept going forever as I moaned and kissed his neck. Then suddenly his grunts started turning into moans and he started fucking me with longer strokes. I felt my pussy get hot and even wetter and realized he was filling me up with cum. He hadn't even asked if he could cum inside of me, he just did it. Honestly - I found this incredible sexy and I started to cum again too as he was shooting his last bits of cum inside of me.

He collapsed on top of me and said "you're on birth control right?". I laughed and said I have an IUD. We fell asleep for about an hour. Then woke up and started fucking again. I really can't believe his stamina – literally one of the main things that lead to us eventually dating…. (Advice to the ladies out there, don’t choose your boyfriend based on sexual chemistry alone. Even if it’s magical. Trust me.) 

He ended up cumming inside of me a second time. Then we got dressed and he went to grab us some coffee. When he came back up we were both dressed and joked around about how surprised our coworkers would be if they knew what happened. It was getting close to when Ben had to leave for his flight, but slowly we started getting closer and his hands were all over me again. He told me I was going to make him miss his flight as he started taking off the clothes I had only put on maybe ten minutes before. He took off his pants but not his shirt and started fucking me hard again. Honestly we fucked so much that I was a little sore but it still felt great to have his strong body over me and his rock hard cock relentlessly fucking me. 

I came extremely loud and told him I wanted to feel him cum. In a few more minutes he was filling my pussy up with a third load of cum. Then he got dressed (again) and left for his flight. I went back to my hotel room and took a shower. As I got out of the shower my boyfriend called to ask about my night and plans for the day. I told him the night was pretty mundane but I felt like I got to know my coworkers "pretty well" and that I was tired and excited to come home. He has no idea what really happened.... I felt guilty. But not guilty enough not to continue the affair for a few more months before finally ended things with my boyfriend.