Sure, we may all hold moral opinions about whether it’s ethical to do so, and many of us are still recovering from the betrayal that is Alan Rickman in Love Actually buying a necklace for his secretary, but we can’t deny that there’s something titillating about an office romance.
A 2019 survey found that 58% of employees have engaged in a romantic relationship with a colleague — but it’s another dilemma altogether when that colleague is your superior.
We scoured the pages of Reddit to find stories from real women about their own hookup experiences. What we found is that they vary immensely — from the lead-up sizzle, to what happens after the coitus, it’s clear that there isn’t a stock standard experience when it comes to sleeping with your boss.
I worked under him for a year and hooked up with him after a Christmas party. He gave me a raise a week later, he left the company a month after that and I was fired soon after for unrelated reasons. We lost touch for a couple of years, got back together after I desperately begged him for a place to live. Three years later he proposed to me. We’ve been married for four months.”
He ended up coming into my house to see my new puppy, we had some more drinks and ended up having sex a few times. I can’t say who initiated it, it was probably mutual, but he did say that he’s wanted to fuck me since he hired me. I won’t lie, I had thought about it too but obviously never acted on it. He slept over and we had sex again in the morning, but never really talked about it.”
I work in a small company with less than 30 employees. My boss owns the company. I joined a few years ago as one of the junior executives. We hit it off well from the beginning. He was divorced and I was only casually seeing someone at the time. As I mentioned earlier, we used to flirt and laugh all the time. It used to irritate everyone but they never said anything. One day after work, I pecked him on the cheek as we were leaving. He grabbed my waist and we kissed. After that, things became heated. That weekend he called me under some pretence. I knew what was up. So I dressed up and we had sex the first time. He was very aggressive and I thought it was because he was sexually frustrated. Only after subsequent interactions did I realise that he liked to dominate in bed.
After that, he gave me a corner office (usually most other junior executives share a large hall). A couple of senior employees resented this but no one ever said anything (not to my knowledge at least). It has been like this for some time.
He comes by my office. We have sex in the middle of the day. He likes to mix office themes with sex — for example, he would have me suck him during my performance reviews.”
It started really slowly, we don’t work directly together but really began to hit it off. I was always excited to come to work but I became more excited just to see him, and I noticed him putting us together on a few things.
One night, after a big day for the company, we stayed in the office and had a few drinks and talked. One thing led to another and I went down on him. A few days later he pulled me into his office to have a talk. He told me it was a mistake, that he was married and it was harassment.
I made things worse. I told him that I was upset for stepping on his marriage, but I was not 100% sure he even was married. I also pointed out that we were adults attracted to each other and could do whatever we wanted. I said what we did wasn’t really a big deal, and that talking about it made it a bigger deal than it was. He basically just agreed with me and said as long as we were not going to make it a big deal it wouldn’t be one.
It was a week or so before we started hanging out at work a lot as we used to. It was not long before we found ourselves alone again. And the same thing happened and it kept happening. For a couple of months, we found time alone together and I would go down on him.
About three months ago we went on a business trip, not together… but together. We slept in the same bed and we had sex several times a day. It was the happiest and kinda the worst time of my life. When we first got back, we went back to sneaking oral occasionally, but we both broke down and had sex in the office a few times during work hours. We spent the night together in a hotel once locally too.
He talks to me and he says he wants to be with me and not his wife but I am not naive enough to believe that. I feel awful about violating someone’s marriage, but I have also had a crush on this guy for so long.”
We had a great time all out together, and in particular, I was able to really talk to my boss a lot and get to know him. I even managed to get him to dance with me, which was a big surprise because he always comes across as the strong, silent type.
It got later and we all decided to head home. I knew that my boss lived relatively close to me so the majority of our journey home was together. I decided to ask him if he wanted to come to my flat for another drink and he said yes. We got back to mine, opened a bottle of wine and went to sit on the sofa. Well, at this point I guess we must both have been pretty drunk because the conversation became much flirtier and I could feel the atmosphere change.
In my drunkenly courageous state, I asked if he wanted to kiss me, and he did. We made out for quite a while, which was really nice. After a little while, me being drunk and horny, I moved my hand to his crotch and got his penis out. We kept making out while I gave him a hand job for a bit before I started to give him head. He seemed really into it, but after about a minute he asked me to stop. I was pretty confused, but he said that he didn’t think what we were doing was a good idea and that he should probably go. I tried to get him to stay and talk, but he decided to leave.
The next day I woke up to a text from him apologising for leaving so suddenly but also saying again that he didn’t think we should do anything together. I was still kind of drunk and courageous at this point and admitted that I had a huge crush on him. He said he liked me a lot, but that he still thought that it wasn’t right for us to get together.
I was quite upset and starting to feel my hangover and didn’t end up texting him again. Coincidentally, I booked a week’s holiday, so I won’t be in the office for a week now. I’m still upset about how things went, but I’m also worried about the atmosphere between myself and my boss when I go back to work.”
When I started working at my current job, I was a hostess. Eventually, I was able to wait tables part-time but still, most of my hours were for shifts as a hostess, which only paid minimum wage. I kept pestering the managers to be made a full-time waitress but there just weren’t enough shifts.
Eventually, my manager announced that he would be leaving to open another restaurant in another state. He ended up taking me aside to tell me that he really wanted to make sure I was promoted to full-time server before he left. I was thrilled! He asked if I’d like to talk about it with him at his house that night. I said absolutely!
When I got to his place I realised right away that there was a total quid pro quo type of thing in the works. Yes, he’d make sure I officially became a full-time waitress. He promised that while stroking my thigh and that’s when I realised what was happening.
Yes, I did it. Keep in mind I never felt threatened or pressured. I wanted the promotion, he wanted sex and I was ok with that. Did it make me feel a little dirty? Definitely. But it was actually a really fun night that I don’t regret.
Was it worth it? Absolutely! At the time I was barely able to pay my bills. I was literally living paycheque to paycheque. In the two years since I’ve managed to save a pretty decent amount of money.”
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