Confessions|My Boss Has the Hots For Me

Confession by Micheal written by Maria Morrow

It all started when I stayed at work a little past the clock out time. My boss works from home but occasionally we see her once or twice a week although there’s a room she used to occupy a year prior to my hiring that still sits there empty. I had been working for the company about three weeks in but didn’t have a chance to officially meet the boss lady until my fourth week in at our monthly meeting. Immediately after the meeting was over, I rushed to introduce myself and ask if we could talk about the company’s expectations for me, something I typically do when I am first hired. She seemed really pleasant and I was looking forward to our next meeting that is until I found myself being inappropriately fondled. That’s right, I couldn’t tell if it was in a sexual way or if it was innocent, mind, I am 25 years old and this woman, my best guess, is in her early to mid forties. She is an incredibly attractive woman but comes off as needy, self-conscious, and sometimes desperate. I’m not hard to look at either, but most do say I have a baby face, whatever that means. It could have easily been misinterpreted so I decided to go forward with the meeting and  get the hell out of there ASAP! I can honestly say, she made me uncomfortably nervous and her being incredibly hot didn’t help the matter.

This isn’t the crazy part, after our one on one meetings, I started noticing her coming by our office a lot more often. It was very unlike her, according to the rest of my coworkers, especially the fact that she was bringing us breakfast and offering to buy lunch, something she had never done since she got hired two years back. Fast forward two months of her unusual behavior, she really started raising eyebrows. SHE MOVED HER OFFICE BACK IN OUR BUILDING! During this time, she still occasionally pet me, but I slightly got used to it telling myself it was just me overthinking and she only saw me as a son even though I never saw her doing it to everyone else. She had made a couple comments here and there about getting a drink some time but I brushed it off, we all make imaginary plans with coworkers to hang out outside of work.

A couple weeks after her moving into our building, I found myself overloaded with work and having to stay in the office past closed time. To my surprise (or not) the boss lady was still inside her office finishing up reports, however, I didn’t think she was aware I was also in the building. I tried hurrying up before she left but with no luck, she comes out of her office to get some water and poor little ol’ me was still in my desk desperately drowning in paperwork. After a couple jokes about work, and tips on how to handle certain assignments, I finally took her offer of getting a drink. She hadn’t been inappropriate that night, which is why I was a bit more comfortable but either way it was a BIG MISTAKE. We drove our own cars, thank goodness! I followed her to a low key local hole in the wall bar a couple blocks from our office building. As soon as we got to the place, I started regretting it. Her fondling didn’t immediately start, but the way she flirtatiously  approached me and made deep eye contact as I spoke, was enough to set a man’s alarm off. Two drinks in and the typical caresses started. Hand touching every time she laughed, legs softly rubbing against each other, that type of stuff. Eventually, I saw her make the decision to go for it, she was about to definitely kiss me when I suddenly looked at my phone as a nervous reaction and decided to call it a night.

I’m not going to sit here and lie and say I didn’t enjoy the attention, I did. I’ve told few of my buddies and they all have conflicting thoughts about it, mainly with the fact that I’m engaged… Two of my friends made a comment about how they would’ve totally gone for it only adding to my insecurities. It’s been about a week and a half since it happened and everything seems to be the same back at the office. I have a feeling she didn’t realize I knew she was going to kiss me since we were both buzzed and I have a feeling I might be in this predicament again and I can’t say it doesn’t excite me. I love my fiance to death, we have been together five years, the last one engaged, though we haven’t set the date. We have an exciting sex life and I think she is amazing, I just think this could be like a cheat day out of my diet, it doesn’t hurt if she doesn’t find out, right?


Comment by Maria Morrow: Micheal, I can’t lie either and say I didn’t enjoy this story, I thought it was hilariously awkward actually, all up until you told me you are engaged. It is completely normal to freak out during the process of a drastic life event, however, it is unfair of you to keep these thoughts a secret, here’s why: More than likely your fiance is also experiencing some type of doubt (considering your age) and it would be a perfect time when you can both provide reassurance and/ or come up with a solution to these thoughts, whatever the solution might be. It is completely unfair for you both to start on a new life together with unresolved issues because whether you would like to admit to yourself or not, there’s something deeper going on preventing you to commit fully. There’s a difference between fantasy and reality, what you do you can’t take back.




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