My Boss [F] had an affair with me [M]

Background: I (M) was single and around 24 at the time. My boss (F) was around 35, married and with a kid.

So, my counterpart at work was scheduled to go with my boss to a conference at a nice large resort. Unfortunately, for him some family stuff came up last minute and I was selected to go in his place since everything had been booked and purchased by the company.

My boss and I meet up at the airport and have different seats on the plane. We check-in at the resort and our rooms are on the same floor but on completely different sides of the resort building. Our first few days at the conference at pretty uneventful. We meet in between conference sessions and trade notes, after the conference for the day we usually have dinner together and then go do our separate things.

It comes around to the final day of the conference, which ends a little early and then all of the attendees are invited to a social mixer with a couple of drinks. So, we each head back to our rooms to change. I get ready pretty quickly and tell my boss to just text me when she is ready, and I will meet her at the elevators. A few minutes later I hear a knock on her door, she needs an opinion of which shoes to wear. Instead of wasting more time, she decides to leave the extra shoes in the room, and she will get them when we check out the next day.

The mixer is winding down and I decide to check out some of the local bars in the area and she decides to accompany me. Which is no big deal as we had been out together for team events that involved drinking. We go out drinking for a little while and are having a good time, yet still professional. By the end of the night, we each have had a few drinks and are feeling good, but still in control of our senses.

We head back to the resort, get on the elevator. I tell her goodnight and we each start heading to our respective rooms. About 30 feet away from one another she runs back to me, and says she wants to get her shoes now so it’s easier to pack in the morning. Me, completely oblivious to everything says ok.

We get to my room; I plop on the bed assuming she is going to grab her stuff and go, and I can simply pass out. When all of the sudden, she climbs on top of me and start dry humping and grinding on me. I try to explain to her all the reasons why we shouldn’t, but she just tells me to shut up and starts making out with me. Me in my buzzed stooper, just decide to go along with it.

We continue making out for a while and I end up getting one of the best blow jobs I think I have ever had. We get ready to have sex and she asks where the condom is. I told her I didn’t plan on getting laid during a work trip so, I didn’t bring one. She just says “Fuck it” and we end up having sex raw. After a few minutes, I am about ready to bust and she tells me to cum in her because she is on an IUD. So, I oblige.

After that, we end up falling asleep and spooning throughout the night. The next morning, we both wake up each a little hung over. The awkwardness and guilt starts to get to her and she is gathering up her things to leave. Me, wanting one more go before we return to reality hops out of bed and starts kissing her and telling her its alright.

We end up having sex again that morning. She heads back to her room to pack up. We eat breakfast together and head to the airport. Knowing full well what happened stays between us and will never happen again, it was a work trip fling.

We arrive at the airport and we are heading to depart. She explains to me that her husband dropped her off and she needed to take a taxi home. Since I left my car at the airport I offered to drop her off since it was on the way to my place. As a thank you for taking her home she decided to give me some road head swallowing it all up! I drop her off at her place.

The following week at work, she calls me into her office, and I assume this is where I get fired. She explains to me that I left a hand-print on her ass from spanking her during our drunken night together. Not completely remembering that, I feel pretty damn cool but then she also mentions she has to hide it from husband.

Shortly after her and her husband separated, so we continued our sexual exploration of one another. Often having sex in utility closets, break rooms or her car during work. Eventually, I found a new job closer to home and with more money, but we continued to date for about a year when she suddenly broke it off wanting to get back together with her husband for the sake of the kid.

Source: reddit.com/r/gonewildstories/comments/u2v21c/my_boss_f_had_an_affair_with_me_m