The Time Me {24 at the time} and my Boss {35 at the time} [MF] had some fun on our work trip. (Part I)

I randomly received a text from a previous boss the other day, and invariably this is where my mind wandered to pretty quickly. A few years after I graduated college I ended up working at a medical education firm. It was a pretty typical job, required some late nights and a little bit of travel for conferences.

(Little background info which you can skip if you want)

Elizabeth (not her real name) was not my first manager at this company. I was on another team initially and ended up getting switched over to hers after a few months. The first time we interacted in any detail was at the company Halloween party. Our conversation started off innocent but gradually became more flirtatious and interesting as the night progressed.

The more we drank, the more we danced and the more “handsy” we got with each other. I was dressed as a Spartan soldier from the movie 300 and Elizabeth was wearing a referree costume – which was sexy but not over the top. We danced a lot that night and I certainly did not mind the way her hands explored along the edges of my costume and her fingernails grazed along my chest.

Elizabeth bore a resemblance to one of the actresses from old school – Sarah Shahi. https://upload.wikimedia.org/wikipedia/commons/7/70/Sarah_Shahi_cropped_and_retouched.jpg https://images1.fanpop.com/images/photos/2100000/sarah-sarah-shahi-2143727-333-500.jpg https://static.tvtropes.org/pmwiki/pub/images/sarah_shahi.jpg https://image.shutterstock.com/image-photo/sarah-shahi-first-cmt-giants-600w-95937169.jpg

I was immediately attracted to her and was getting extremely turned on by her advances. Apparently she had hooked up with a younger guy at a company party a few prior to that, and someone made a comment to her about that, and Elizabeth seemed embarrassed and her whole entire demeanor changed and unfortunately nothing happened that night.

A few months after the Halloween I ended up being switched account and began working on Elizabeth’s team. Nether of us brought up that Halloween party, and we developed a very good personal/professional working relationship. Occasionally we would go to happy hour after work – sometimes with colleagues from our office, other times with colleagues from different companies & maybe a combination of both. The tipsier we both the more noticeable our flirtations got, often saying things like we wished we could go back to that Halloween party.

(If you aren’t interested in the buildup, you can just skip to this point)

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Several months progressed and it turned out that we worked really well together. I’m not sure how much of that can be contributed to the palpable sexual tension. That following May, we had a work function that brought us down to hilton head, south Carolina for the weekend. One of the partners was also supposed to join us but wasn’t able to at the last minute.

Elizabeth and I got down to the location a few days early so we could set up for the conference. There was also a good amount of free time for us to relax and take advantage of the awesome amenities of the resort. We spent a good amount of time at the pool, on the beach, by the hot tub, and by the bar at nights.

Spending all that time with my manager, in those capacities, just the two of us – really intensified the sexual tension between us and reached its peak on the Sunday before the conference was going to take place. That night we were at one of the more secluded hotel bars, just the two of us. The flirting, conversation & exchanging of touch really suggested that something was going to happen that night.

Elizabeth even pointed out one of the members of the hotel staff who she said was looking at & flirting with me earlier in the day by the pool. She kept teasing me saying things like that she would find out just how good I was, since our hotel rooms were right next door to one another. I quickly replied saying something along the lines of “well we certainly don’t need her to figure that out” I replied in jest, looking directly at her with a seductive grin on my face, to try and make things as clear as humanly possible.

Elizabeth and I finished our drinks and began making our way to the elevator, Constantly exchanging glances and flirtatious giggles. We got into the elevator and it almost was completely shut before another hotel guest obnoxiously threw his arm through the elevator doors so they would open back up. I was a few seconds away from throwing Elizabeth up against the elevator walls and passionately kissing her. And to make matters worse, the other guest was on the same floor as us so we didn’t have any time alone in that elevator.

Once we got off and began walking toward our rooms, I could tell something was off. Elizabeth was much stiffer, wasn’t smiling or laughing anymore and was hardly even looking at me. It seemed like all the air had been taken out of the building. She barely even glanced at me as she fumbled with her room key and then muttered “good night” under her breath as she scurried into the room . . .

Source: reddit.com/r/gonewildstories/comments/lwdhby/the_time_me_24_at_the_time_and_my_boss_35_at_the

1 comment

  1. I always wonder, what if all of the flirtiness was perceived only by one party, and the sexual tension was one sided?
    In these stories, right as something good is anticipated to happen, at that point the horny associate finds out that it is his/her misperception.
    I want to see that on a Larry David episode.

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