First and foremost, I’m a serial cheater.
My boss and I had become good friends often times we will go to lunch together and our conversations had mutated to subjects that were far from work related. This how we learn each other intricacies of each other lives, which allowed an emotional attachment to develop. She learned too much about me and my fractured relationship with my SO, which probably turned her off as she was attracted to me but was scared to get in the way. After a recent fight with my SO, I had decided to share the previous night’s events with her during lunch. During this time, she grabbed my hand and reminded me that she was in my corner and I had every right to be happy. This was a sign that things will start spiraling out of control with her, that evening we spent time having a drink after work and during this time the gloves came off.
I wasn’t interested in talking about me and we talked about and her struggles, however after a couple drinks we were holding hands waiting for someone to make a move. The standoff did not last long and we started making out, we were making out like a pair of highschoolers in a booth at the corner of a bar while a couple on lookers staring. It was guilt that pulled us apart and she apologized briefly. I didn’t want to hear anything about it and shut her up by giving another peck in her mouth. At this time, we knew were things were heading and we left the bar holding hands with no idea where to go. Driving to her place was 12 miles away, and there wasn’t a chance in hell to get to my place unless I had a death wish.
We got in her car and drove down the boulevard looking for a motel. After a couple of blocks and over the bridge in to the next town we reached the Royal Motel, the place was empty at 7 PM, the owner knew we were up to no good when I approached the check in window. I negotiated for a room, he knew that we weren’t spending the night and cash only was the way to go. After getting the key we headed for room 12 holding hands. To our surprise the room was clean, but we couldn’t be so lucky when we turned the TV on it was full volume on a porn channel, we both laughed and look at each other amused.
We started kissing again and ultimately we ended in the bed rolling around while our bodies rubbing against each other. Our hands knew each other’s targets and we gently squeezed them. After cooling down a little we stared at the ceiling mirror without saying much as we lied next to each other. I grabbed her hand let her down towards my cock, she began squeezing with ferocity. She slid down and undid my belt, slowly pulled my pants and had a stare down. Her soft mouth began to stroke it and the only thing I could was watch her perform from the above mirror. My boss had passionate skill, she alternated between hands and mouth and I couldn’t tell who was doing the damage. She got me to the point of no return but instead of pressing me to finish she just left my cock alone, a stream of semen rolled down my shaft in to my balls. Those were the tortured tears of angel, I had orgasm but no joy. However, my cock was still as hard as before, she grabbed a the cum rag. It was fresh towel and with it cleaned the slight mess. She was highly turned on by the spectacle, and we were kissing again ferociously. I pushed her to the side and demanded her to get on top of me.
Her smile said it all and obediently got off the bed undressed and crawled backed. We were joined now. She was grinding me and at the same time trying to suffocate me with her kisses and breasts. But, I put an end to this threw her to my right and now I was on top. I was fucking her like I wanted, short bursts followed by more playful long strikes using my hips. These long strokes drove her inside deeper and deeper. Her two hands were the only way to confide the groans and moans, they rested on her mouth trying to muffle her feelings. She was all mine, but I could tell she was hanging from a string about come crashing down. When she couldn’t hold it no more and she came, her body twitched, but now she was soft and tender. She was done, I pulled my cock out and stroke it and finished in her belly. The cum rag came handy again. We stared at each other acquiring intel of all the uncharted parts we missed in this quick huddle. We got dressed walked out hugging each other with the smell of each other.
However, reality set in, she had to get the pill and the guilt grew and we had plenty of awkward silence for the next couple of weeks. Until our lust took over again.
Source: reddit.com/r/gonewildstories/comments/6okh8q/cheating_with_my_boss_at_a_motel_mf
Good way to lose your job