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Three Men Who Slept With Their Boss

The sneaking around. The power dynamics. The aftermath. What’s it really like?

Apparently, 61 percent of guys fantasize about having sex with someone they work with. But how complicated — or untenable — does it get when that person is your boss? Can you even have a normal relationship with someone who exerts a certain level of power over you? To find out what it’s really like, we talked to three guys who lived through it.

It Was Fun(ish) Until Everyone Found Out About It

Daniel, 33: At first, people we worked with at the restaurant had no idea I was sleeping with the boss. I was single, she (my boss) was single and the whole thing, at the start, felt like a regular hook-up.

But then, one night right before opening, some of us were looking at the new schedule and one of my coworkers joked that he should sleep with our manager to get the shift he wanted. There were a few “oohs” and laughter. That’s when I became aware that people knew. I just laughed and said it doesn’t actually help.

We liked each other, and the sex was great at first. It was basically mutual, us wanting to hook up. Did I feel pressured to sleep with her? At one point, yeah, a little bit. It’s not like she could have fired me, but it probably would have made things difficult and I didn’t want the drama. We are about the same age, so it wasn’t weird for us to hook up, not like a Harvey Weinstein situation. But still, because we weren’t a real committed couple, the feeling that she was my boss was always kind of there because we had to sort of keep it to ourselves, and then it felt even stronger when other people found out.

I think in the beginning people guessed about it because my boss and I were respectful at work. Neither of us really wanted people to find out. But a couple nights we’d go home together at the end of the night, and people probably saw it. Then one day, maybe three weeks into our thing, my boss and I woke up together and spent the next day together on our day off, and we ran into a girl we worked with, which was awkward. After that, we were both basically like, “Well, the secret is out now.” Not that it wasn’t allowed at work, so it wasn’t the end of the world, but there wasn’t any upside to people knowing. She told me she didn’t want people to think of her as the type of manager who sleeps with her employees, and I didn’t want people thinking I was sleeping with my boss for favors. There wasn’t a corporate ladder to sleep my way to the top of, but still, it was an uncomfortable situation to be in.

Eventually, it just kind of lost its spark for me, like in other relationships. I didn’t want to date her. We got along fine, especially working together, but I didn’t like her perspective on things. I couldn’t see us getting along as a couple. I think that’s where it was headed, into relationship territory. So I told her instead that I didn’t feel comfortable with this anymore, with everyone at work knowing. I could tell she was upset but she didn’t want to reveal it. We didn’t tell the people we worked with that it was over — it didn’t come up — but they figured it out on their own the way we acted around each other at work after that. Which was awkward, but not horrible. We both kind of downplayed it.  

Still, a few months went by, and we slept together again after a birthday party we were both at. That was the last time. That was all a while ago, and we both moved on, though I left first for another job. We haven’t talked in years, but we follow each other on social media.

It Was As Though It Never Happened

Philip, 32: My boss wasn’t the person who hired me, but she was higher than me on the ladder, so at first she was my superior. Then the boss in our particular department got laid off — probably as a cost-cutting move — and she became my direct boss.

We’d already been working together for a couple years. We got along great, but there was always some sexual tension there; it was fairly obvious. She was really good looking. We were friendly and I liked her as a person, but we didn’t flirt — we were basically a little shy and awkward around each other. She was a “nice girl,” and didn’t have a potty mouth like others at our office, so I never knew what was coming.

She was married, by the way. I was single, although girls at the office would joke about their “work husbands,” and I’d overheard that her work husband was me.

One time we were in a conference room going over some planning for the next few months. We always worked as a team, so it was something we did together. It was just us, at this big table, alone in this room with no windows, and no lock on the door. We were sitting next to each other and — this sounds so junior-high — at one point our legs were touching. They continued to touch for a little while. We could both feel it.

The work conversation started to trail off. Then we looked at each other for a split second, and we each just went for a kiss. I’d never seen it coming, so it was surprising. We made out for a few moments, I guess. The “meeting” ended quickly, without us saying much, just smiling, giggling and quickly wrapping it up, which was awkward, but I don’t think either of us knew what to say. I couldn’t stop thinking about it. Then I emailed her later in the day to see if she wanted to get lunch the next day. She said yes.

I lived close to that office at the time, and that’s where we went. The sex was good. She wasn’t a very demanding boss, so it didn’t feel like a power trip, it was just … regular sex. The fact that I was doing it with my boss didn’t really go through my head.

It was one and done though. We never did it again, and I swear it never came up. It’s hard to explain, but that’s just kind of how we interacted. After a while, it was like it never happened. I’m guessing there was some guilt involved. I felt bad about it too, in a way. I don’t think anyone at the company knew about it because it was so brief. I got moved to another department about a month later. I don’t think she had anything to do with the decision, it was way above her, but that was that. She left the company a year later. I’m still there. I honestly don’t think about it that often.

It Was A Night the Storage Closet Will Never Forget

Antonio, 41: My boss probably could have gotten fired for the things she said to me before and after we had sex. I didn’t tell, though. She was a boss in the company, but not my direct boss. She was definitely sexy, and whenever I’d walk past her, or see her in a meeting through the window, I could feel her eyes on me. She was also really friendly when our paths did cross.

Then at a holiday party, we were standing at the bar together. Others were close, but I don’t think they could hear us. She was telling me about her family. She had a kid but was separated from her husband or boyfriend (I’m not sure what he was), and she was making that clear to me. Then she looked in my eyes and said, “If I hadn’t had so much to drink I’d take you into that bathroom over there.” I didn’t really know what to say to that — she had had a lot to drink, for one thing.

Nothing happened that night, but then she started emailing me at work. Some of it was just stupid things — jokes or random thoughts from her. I stopped responding to them, then she sent an email that said, in Spanish, “I WANT TO FUCK!” I think it mentioned one of the office bathrooms.

I’d been thinking about that holiday party ever since it happened, so I asked her to meet me in the storage closet for some help with filing. She met me there. It was almost animalistic; she was wild. There was nowhere comfortable to do it in that room, so we did it standing, with our pants around our ankles or with one leg off. It was great sex under the conditions, but also it felt like a relief when it was over.

I’d heard gossip that her ex-husband or boyfriend was a shady guy, possibly in jail, so I was immediately worried about getting more involved. I stopped returning her emails, which were pretty much the same, and I stayed on my end of the office. It was kind of stressful for a little while. For one thing, you don’t want anyone else to see an email like that on your computer screen or over your shoulder. I don’t know if anyone else found out. It was a weird place to work, with a lot of strange characters. It wouldn’t surprise me if others were hooking up, too.

After a while she got the hint, and luckily, I didn’t have to take it up with HR. When I did encounter her at work we would ignore each other and try not to make eye contact. She left a few months later. Talking to others after she left, it sounds like she wasn’t that good at her job. It wasn’t a very good company either, though — people came and went all the time.

I haven’t had sex in a storage closet since then. I wouldn’t really recommend it.