“I Slept With My Boss—Here’s What It Was Like”

Ever fantasized about sleeping with your boss? What if that fantasy actually became a reality?
Well, for these four women it did. Here are their stories—firsthand.

“I actually think we’ll end up together.”

“To be real, it was only a matter of time before it happened. During my interview, we flirted the entire time, and he gave me his personal cell number before he hired me. I worked as his assistant for two months before we ended up at a bar, taking shots, which led to kissing. It went downhill from there, and we officially started a relationship. It’s still a complete secret from everyone we work with. I brought him home for the holidays and my parents and family know. I think we’ll get married in the future. It wasn’t a good idea to get involved with him, but you can’t help who you fall in love with.” —Marcy D., 31


“I blame it on our Christmas party.”

Christmas parties are never a good idea. I ended up getting really, really drunk and spending the night with my boss. Neither of us had any chemistry or feelings for each other beforehand. It was a drunken mess, and we both woke up the next morning embarrassed. I was scared I’d get fired. My boss was scared I’d tell people. It was so awkward for the first couple of months because I directly report to him and we have meetings once a week—just us. A few months later, we both chilled out and decided to put it behind us. It’s been a year and we’re finally starting to act normal. I would never, ever do this again with a boss. Our Christmas party is next week, and I’m not even going.” —Liz H., 29


“I did it right before I planned to quit.”

“I’d call the sex with my boss revenge sex. I was planning on quitting in the next month or so because my boss was awful and I wanted to move on with my career. I figured it would be a lot of fun to sleep with him and then quit because he’s super hot. He’s just a hot asshole. I asked him out for a drink, and then we slept together. Two weeks after the first and only time we hooked up, I quit. It was right before the holidays so he wouldn’t be able to find someone to take my place for a while. I never spoke to him again.” —Debby S., 31


“It’s my best kept secret.”

“I’ve been hooking up with my boss for two years. We aren’t dating, but we do have something pretty consistent going on. Nobody in our office knows and when we are at work, we pretend like we’re hardly even friends. It kind of keeps my life interesting. It makes me wonder if other people in my office are sleeping with their bosses, too!” —Carrie F., 27