People Candidly Reveal What Happened When They Slept With Their Boss

It’s a cliche which has long been perpetuated by the media that beautiful women who managed to advance pretty highly in their careers must have “slept their way to the top”.

I mean, generally, top positions in corporations are dominated by men, so people make the assumption that women have no other option but to use their sex appeal to convince their superiors that they are worthy of a promotion.

Of course, it’s a pretty sexist assumption to assume that a woman can’t be both beautiful and accomplished. However, despite this, sleeping with someone in a position of power, is actually not hugely uncommon.

And it’s not just straight, conventionally attractive women who do it – people of all kinds of genders, orientations and physical appearances have crossed those risky boundaries, with varying outcomes.

The following Redditors either found themselves in this situation or knew someone else who did, and their stories are juicy AF:

1. One thing led to another

“When I was 18 I was part-time running food at a really high end Italian restaurant. After shifts ended everyone went to the bar next door and got s***faced every night. One of the managers was a 24 year old blonde that I really had a thing for.

After a night at the bar we were loaded and she said I could crash at her place. So I went and one thing led to another, we f***ed and I took a cab home.

The next weekend when I had shifts the managers called me in because they fired the bartender and because I’m “very hard working” that I’m going to fill his position. Maybe not an “office promotion” story but I was making a couple hundred more a night bar tending than bussing.

Edit: For everyone losing their marbles because I wasn’t 21, I live in Canada so 18 is the legal drinking age. – The tips were amazing, on a good night I could clear a couple hundred because I only worked there Fridays and Saturdays.

Edit 2: I live in Alberta so it’s 18 here. I’m drunk right now can confirm.”

2. A true love story – of sorts

“I was the boss sleeping with my employee. She was a very mediocre employee to begin with, raging alcoholic, would come to work looking like hell with black eyes and wet hair, never on time. After we started sleeping together I think she developed the attitude that she had to start performing better at work or it would be obvious there was something going on when she didn’t get fired.

Within a few weeks she’s a model employee, probably far better than even I was. She received several small lateral promotions within a few months, one I was involved in and one I was not. We ended up dating for over a year while I was still her boss before we both left the business.

We both started looking for other employment because of our relationship and found better jobs with better pay. A few years later we are still together and now living together and engaged.

3. He even got a raise

“I slept with my boss. We were all out having drinks and were sharing a cab. She told the cab driver to just drop both of us off at her place and I gladly went with it. I transferred to another department shortly thereafter because we both agreed it was weird now. Unbeknownst to me, I was giving a raise and a new title when I transferred. I always thought of it as a reward for being discreet. I had sex with her because she was a hot older woman, the raise I got later was unexpected. “

4. Not bad for a summer job

“Pretty awesome. She sat on my face, and I got three bucks more an hour to lifeguard the local pool. Best summer job I ever had.”

5. She has absolutely no regrets

“I had sex with my manager so I could become a full-time waitress. 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 GM and AMs to be made a full time waitress but there just weren’t enough shifts at the time.

Eventually my GM announced that he would be leaving to open another restaurant in another state (not part of our small chain; completely different franchise). 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 realized 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, though, and that’s when I realized 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 okay 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 paycheck to paycheck. In the 2+ years since I’ve managed to save a pretty decent amount of money. When it’s not killing me I like the work, too. But if I’d had to wait for that promotion, especially after that GM left, it would have probably been months before I became a full time waitress. There’s no way I would have been able to manage that and I’d have probably ended up getting a different job. So yeah, I was happy with the results.”

6. A cautionary tale

“Girl just returned home from being an air-hostess for a few years. Got a job at my work. Tele-customer services. (everyone bangs everyone in CS) She was school friends with my boss so, we saw a lot of each other. We got on well, started sleeping with eachother. She moved into her own home and asked me if id join her…Foolishly, I said yes. 6 months later, using her connection with her friend in the company, she got a promotion and new job role in training and HR. Tiny bit more money but more importantly, she was now MY boss…. you can see where this is heading.

Another 6 months later, we started to have some issues and agreed that we should work at it. It was, for my part, the fact that we were together 24 hours a day made me feel a little suffocated. From her point of view, I wasnt ambitious enough. She told me to go for jobs I didnt want to do in the company because “It looks better for us”. Anyways, a little resisting her urges for company promotion and my own plan to go to University part time, to study for my dream job, everything seemed to get better.

Then, it stopped being better…

We drifted even though we were still together constantly and after deciding to give it one last go, she dropped a cannon ball on me. She told me she had been sleeping with not only her boss but with the company director and a co-worker. I asked how she could do this, it boiled down to that she did it because she wanted to, without regard for me, just to progress her career… rest assured my world crumbled.

I was embarrassed at so many things. Being cheated on by your GF is one thing. Being cheated on by the person you share a home with another, being cheated on by a co-worker is something too, but being cheated on by your boss with members of the same company….After we broke up I tried to continue working at the same place. But it became very clear that she wanted me gone and twice went to her boss to find a way to get rid of me (I found this out from our mutual friend years later) I couldn’t take it anymore and quit.

I went numb for 4 years after that. Went to that bottom of that barrel everyone talks about. I was Low, very low. I felt completely lost and alone with my troubles. I had no idea where to go, what to do and thinking like this was just my fault, deal with it. I lost a good job and a bad girlfriend. I gained around 100lbs. I cloistered up socially. I thought that I was weak to need help for feeling ‘a bit down’ That this is something you cant ask for help to deal with, no one cares. This went on for years. I remember genuinely thinking that everyone around me would have their life improved if I was simply dead. I was diagnosed with Depression and Social Anxiety with suicidal tendencies.

But, things are getting better for me. Ive lost 84 lbs of the 100 lbs I put on in the last 18 months. I have re-signed up to finish my degree in September of next year. I volunteer regularly at a local mental health charity that helped me during my problems. Don’t sleep with anyone you work with. It can’t only potentially ruin your job, it can ruin your life. She is now a stay at home single mum… worth it, wasn’t it, dear?”

7. She tried and failed to sleep her way to the top

“My dad is the boss of a mid-sized company (no, this isn’t an incest story) and he hired this girl a couple of years back who was quite young and attractive, and seemingly thought she could use her s*x appeal to get a promotion. She started coming on to him, and he made it really clear he wasn’t interested, he was very happily married and she was 36 years his junior, he thought it was weird and creepy.

The girl wouldn’t take no for an answer. It started off as really outright flirting, looking for excuses to touch him, wearing inappropriate outfits to work (the office has a strict dress code for employees and she was definitely breaking it, one day showing up in a very transparent men’s white shirt with no pants and nothing underneath, one day wearing a sexy Halloween costume on a day that wasn’t anywhere near Halloween), and other such behaviors that whilst annoying and weird were harmless.

Then she started to send him really explicit emails and pictures of herself, groping him as he walked past her, trying to kiss him, etc. He ended up firing her on the grounds of sexual harassment.

A few weeks later there was an office party and she showed up and somehow got him alone, climbed on his lap and told him she’d do anything to get her job back, and started to unbutton his pants. He pushed her away, told her he wasn’t interested and if she tried anything like this again he’d call the police. She told him that she “Was never interested in an old prick like him anyway”, that the only reason she had tried to seduce him was to get a promotion, and that “Any guy would be lucky to have me, you must be a total fag to turn this down.” A few weeks later a similar thing happened, she showed up at an event she wasn’t invited to and tried to have her way with him in order to regain her job. He called the police. They charged her with sexual assault, and she got off on community service but would be registered as a sex offender.

Then it got really scary. She started showing up at our house, threatening my family, saying my dad had ruined her life and that she was going to make him pay. One day we came home to find her naked in my parent’s bed. On another she showed up at my school claiming she was my mother and needed to take me to an appointment. Luckily the receptionist knew my mother and told her to leave, wouldn’t let her get anywhere near me. We called the police again and they took her into custody, and then to a hospital where she is now receiving mental treatment.

Moral of the story; Don’t try to f*** your boss if they’re not interested, seriously, it’s not going to end well for anyone. Actually, don’t f*** anyone if they’re not interested, consent is vital.”

8. His professor “gave him an A”, he “gave her the D”

“Male here. I had sex with a professor when I was 20 (she was 42). It wasn’t for an A, but I got one (to my own credit, I was a good student). It was nice having an experienced woman to sleep with. We had a brief relationship and then ended things when the semester was over.

Was it worth it? Yes and no. Things were rough with my then-girlfriend, so I (very incredibly regrettably) cheated on her. Lowest moment of my life. Even though we’re not together, and haven’t been for about 7 years, I still live with guilt. The guilt was not worth it. Also – at alumni/reunion events, there is always an awkward conversation (Professor was also an alumna).

But a lot of good came of it: I stopped questioning my self worth pretty much then and there. I thought my girlfriend was as good as it got (and it wasn’t good), and I realized that despite being a scumbag, I obviously have attractive qualities about me. Attractive enough for a professor to jeopardize her career to sleep with a student… I never want to revisit this guilt.

I never came clean to my ex, and to this day she doesn’t know (Wore condoms, I was tested, came back clean, didn’t have sex with her in the interim), but I don’t want to do that to someone else, or myself. So – communication. It taught me the importance of staying open and keeping things in perspective. I cheated because things were bad. I had an opportunity and took it. Today if I get to that point, I have a serious conversation and end things before cheating happens. I know that sex is good, but it can be AMAZING. I never had mind-blowing sex before, and a fit 42 year old can provide it after a long life of experience. That was nice. tl;dr – Professor gave me an A, I gave her the D. Was worth it in some ways, but not worth it in other ways.”

9. They both slept their way to the top

“Maybe mine doesn’t count, but I was the boss that f***ed one of my employees… at first. To be fair she was hot as f***, and I had known her since I was five (we started kindergarten together). I had encouraged her to take the job, and we had had a relationship prior on some level, though nothing really serious. We had lost our V cards together early on, but it wasn’t a relationship deal.

She did get a huge amount of preferential treatment, but even if she didn’t f*** me stupid she was a superior employee (nice perk). She had the first pick on hours and had first pick of assignments. We didn’t hide our relationship. No staff complained (save for one girl that already hated me). My employee f*** friend was well liked because she enjoyed taking the hard assignments (mmm), and she’s so genuinely sweet nobody could really dislike her. Yeah, she f***ed me, but everyone was f***ing everyone there. We were young.

I left the job because I was just over working there and started doing several part-time jobs so the week wasn’t one monotonous blur anymore. One job I had was janitorial. So guess who applied at my janitorial job? My sexy ex-employee. This time she was the manager. I f***ed my boss like crazy. She took the job because she knew I was there. She promoted me to full-time assistant manager the month she got settled in. We are married now. Several of our ex-employees/coworkers attended the wedding, two were in the wedding party. 16 years. We work well together, but we both took different career paths. We no longer get to have mid-day romps save for the weekend. Yesterday was particularly nice, though. She was off work before noon.”

10. Oh, the drama

“My best friend and roommate (separate rooms!) in college slept with her boss. She worked as a receptionist at a law firm. He was a freaking creep. She was 18. He was in his 40’s. He wasn’t cute or nice. He moaned like a girl and it was disgusting to hear. I always lectured her about it but she did get a lot of perks. For example, he would pay for everything including giving her $100 bills nearly every time they met up. He would buy her lunch every day at work. It was pretty much a sugar daddy situation.

Long story short, one day he came to the apartment and started banging on the door, yelling. She wasn’t home and I did not answer it. He found her on a dating website (a sugar daddy one) and became scary. Fortunately, he left that time, but we ended up calling the police because he was threatening her. He went to jail for some crap and I moved out shortly after that. We’re still good friends though.”

11. They couldn’t keep their hands off each other

“I was pretty good friends with my boss who was a few years older than me, we always had a high sexual tension. She called me her “assistant” even though I had basically no job title. I would always joke about getting rich and running away with her.

One day she was transferred about an hour away from where we worked together and was replaced by a total douche bag tyrant of a new boss. Since we no longer worked directly together something must have clicked and made it okay to invite me out drinking with her. A few days before actually seeing her she was messaging me with all kinds of hints and obvious innuendo.

I went out with a friend so it wasn’t awkward if something went south. She ended up buying us both drinks all night, setting my friend up with her friend and paying for a cab back to her house. For some reason, sex with someone who you’re technically not meant to be banging is always the sweetest, and I think she really got off on that. I had absolutely no goal apart from to score with me smoking hot boss. After sex we went outside she was wrapped up in a bed sheet and I was in my underpants sitting out in the cold having a cigarette. She said she knew I wasn’t happy with my new boss, so she asked if I’d be interested in a new job… With our major competitor. She let me know she’s already taken a position her self and could offer me a better job than I already had. I promptly accepted and suggested victory sex. She was very firm and said not to push my luck. Ultimately got horny again and woke me up for a midnight snack.”

12. Plenty of regrets this time around

“Two years ago, the guys around my cubicle were borderline sexually harassing me. I didn’t want to bring it up with HR because I made that mistake with another company and that’s a whole mess of drama I don’t want to deal with again.

I went to my manager’s office, hinting that my coworkers are pushing me to the point of quitting. He brings up an open position that pays an extra 75k per year that will have its own office and I can stay there secluded for most of the day. The way he looked at me, I knew what he was hinting at. I asked him when he wants to talk about it. He says he’ll pay for a motel and we’ll both get off two hours before work ends. Nothing straightforward was said. I couldn’t even text my husband for the rest of the day. I arrived and we were there for around an hour. No one ever got suspicious afterward.

Was it worth it? No no no NO! The next morning, I realized something very important. I didn’t need that extra money. I could have just quit and found another job. Now I feel like an outcast in my family, a person who would sell out love for money.

I convinced my husband to put the extra money until our kid’s college fund for a few years, and then until a vacation account for when they’re in their late teens and we can go on a nice cruise, possible have them bring their girlfriends or boyfriends. I’m not spending a dime of that money on me, and I know that’s not enough to make up for what I did.”

So there you have it: there is no singular type of “sleeping your way to the top” experience. It’s an experience people from all walks of life have made and vary greatly from immense regret to an unexpected happy ending.

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