Fantasy: Sleeping with the Boss

Photo Credits: MEN

Have you ever fantasized about sleeping with the boss?

Say, you’ve been working with him closely for two months and already you’ve been together everywhere: a three-day business trip, you guys worked overnight together on a project, spent several working lunches. The next thing you knew you are fantasizing or wishing that your relationship with him would progress into a sexual one. You fantasized about the two of you rendering an overtime work together on a weekend and no one was around and you had sex in his office. Or maybe the two of you went out for a drink after a successful project launch and somehow you guys ended up in bed together.

While the idea seemed hot, I have never fantasized about sleeping with a boss, or even with a colleague. I never had an office romance either. What about you?

Or maybe it wasn’t just a fantasy for you anymore because you already slept with a boss or a coworker in the past? How did that go for you? Maybe you are currently contemplating to do so?

If you are (thinking about it), bear in mind that this sounds like a sexual harassment suit waiting to happen not to mention some companies do have anti-fraternization policies. Also, every single office affair I’ve ever known ended up in Splitsville and it mostly ended with either one or both of them resigning from their jobs because the workplace became too uncomfortable for them. And if the affair is made known to everyone?

You guys become rich fodders for the office gossip mills.

That being said, have you ever fantasized about sleeping with your gay boss or maybe that hot colleague? Would you or have you ever acted on that fantasy? Why or why not?

Share with us your thoughts and stories in the comments section below.

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  1. Randy

    Those two hot dudes in the photo sure do not look like they are sleeping.
    I’d like to do what they are doing with several of my employees.

  2. Manny

    Office relationships can work if both parties or more are respectful and know their limits.
    Never showing jealousy or trying to be always next to the person, (not being possessive) and keeping your personal affairs away from your working relationship/s.
    I met my husband at work we date for 6-7months then got married. Now going on our 12yr anniversary.
    When we announce our wedding and passed out invitations to our office co-workers people were in shock, that we were engage and getting married.
    We also hold an open relationship THAT WORKS FOR US..
    It’s all about knowing your limits and respect.

    • Danny

      LOL! I had an aunt and uncle meet like that,except their seeing each other was for over a year.
      Since the company they worked for did have the non-frat policy so it was no more than Good Morning, Hi,what’s up? at lunch and “Later see you tomorrow” at the end of the day. They kept it quiet until they announced their engagement Over 45yrs. ago, 3 kids,2 grandchildren later.

  3. arturo23

    I’m the boss!
    Last winter, a very-good-looking fellow is assigned to help me with a client presentation in Buffalo, NY. We stay at the airport hotel, have dinner, but he’s looking at me, just won’t stop looking. Dropped things a couple of times, so he could brush me lightly as he bent down to retrieve his item, but I’m still clueless as to his intention. He heads back to his city, I go to mine.

    The following month, he offers to make the travel arrangements, and for some reason the airport hotel is full. We stay at a place downtown, and after work he suggests the bar across the street. Pretends not to know it’s a gay bar! We walk in and he’s still looking at me, finally saying ‘what do you think, is this OK?’ Now he tells me his intention, he was hoping to get drunk and have me carry him back to my room.

    Sex is more fun if you’re still sober enough to remember it the next day, so we dispensed with the extra drinks. We had a great time, doing what men do- he had a short but super thick cock that was just right for sucking, he grunted what I took to be approval of mine in his mouth. He went back to his room afterwards, went back to his city, and was assigned to a different project the very next week. He keeps saying he wants to come back and visit though….

  4. Justin

    Yes, I have fantasized about this! Work with a really hot manager at my work in retail, haven’t acted on it due to the sexual harrassment part plus I think he is straight, but there has been several fantasy’s about him, from heading over to his or my house after work or for a weekend or a fantasy of the 2 of us being locked in a room together alone. When he’s near by and I smell his cologne or whatever he uses, that sends me over the edge and makes me want him even more lol.. I’d love to act on it if I could but like I said afraid of the consequences

  5. Hunter0500

    “…and somehow you guys ended up in bed together.”

    The notions of “ended up” or “found yourself” are absurd. If that’s the case, you’re an irresponsible child who has no business being in charge of an adult body. And you have no reason to whine or complain or call yourself “victim” when your world comes crashing down in misery. As they say about money, a fool and his job are soon parted.

    You and the boss or coworker need to keep it in you pants long enough for one of you to change jobs. Keep in touch. Agree there is an attraction. But be a responsible adult adult and agree that dating in the workplace does not go well long term. Agree not to date or have sex until one of you has left the business. Given today’s turnover rates, you can expect it’ll only be a matter of months before one of you finds a better job, is terminated, has his position cut, etc.

    • Exmil

      You are about the only poster with old fashioned civility decency and common sense, that I read on here… Sadly the world we came from has departed from us long ago, for this mess it is now.

    • Exmil

      99 percent of the sexual discrimination and harrassment claims come because morons did not grow up with boundaries or and kind of civility instilled by their parents. In my book, if you have problems at work with your coworkers and boss, it’s not because of your sexuality, it’s because you push your (not you or yours, Hunter0500, but in general) sexual preferences, or politics and conduct on others who quite frankly don’t want to know, don’t want hear it and they react accordingly by being disgusted and reactive to it being shoved in their faces and down their throats. After reading many of the posters on here on many topics, it is the core reason why alleged victims are not victims at all, save for their own selfishness and lack of sense, common or business wise. If the dipsticks had basic upbringing, boundaries, dignity and restraint, nobody would care what they do or how they live. Its their lack of respect TOWARDS other people that makes the public hate them.

  6. Rob

    I’m in the closet yeachsr and my straight gym teacher buddy have hung out a few times. I’m average build and he’s very muscular. When were out drinking a few times he loves to piss in the same bowl as me and has stared right at my dick a few times. In the bathroom at work I’m sure he’s peeked as well but not as obviously. It’s never amounted to anything more than that but hey you never know.

  7. Erotikbottom

    I’ve slept with my boss back in 2004(I was 25 then and he was 43) a really hot 6’4” toned silver haired hunk of a man with bedroom eyes and a killer smile.

    He absolutely slayed my hole while we were staying in Vegas for a workshop. Good times.

  8. latinlust69

    Sleep with the boss?! Eww. Most of my bosses have been women. A co-worker or five, yes. I’ve worked with some hotties. Seen some naked too. There was a hot mailroom boi, blond, blue, bubble butt. There was a built silver fox. Never did one, really wanted too tho.

  9. Rano

    It creep me out when one of my subbordinate want to have sex with me. That person blantly told me. It ruin the whole image being a team player, i endup quit because he becomes obcess with me and he stalks me. Crazy and creepy

  10. SquashMA1987

    Have had sex with the boss here. I was 28, he was about 44 when it started on a business trip, sharing a hotel suite. He needed data for the meeting with the client at 10am; I was at the desk in the hotel room working on my laptop, just in a kinda snug tee and gray spandex boxerbriefs when he woke up about 6:00. It started when he leaned over my shoulder to view the laptop screen, his warm shirtless chest against my right shoulder, him balancing himself with his left hand on my left trap. He was happy with the charts I had put together and started to massage both my traps and the back of my neck. My nips got hard and my cock got hard, and things went from there. We’re only active when in hotels out of town, but the business trips do seem to be coming more frequently lately. He books the hotel suites himself, so I don’t think anyone at the office knows.

  11. Richard

    I have never slept with the boss before, but have often fantasized about it. There are some guys in the office that would like I would like to play with but have not acted on it yet.

  12. Scott

    I never slept with my boss… I had the next best thing ….his father …We all lived in the same town ..we hooked up a couple of times…He was 55 and I was 35 . I found out after the first time we meet . Who he was…

  13. Jim

    I haven’t slept with a boss. I did have an existing sex buddy who got a job with my company. I have an office, so over the 4 years he worked here, we had a lot of sex in my office. He especially liked to slowly suck me off and ride my dick when i was on conference calls. We got really good at making almost no noise. The hardest part was the cleanup, but we got good at having everything stocked in my office. He is still a buddy of mine.

  14. Sarevok

    I did. In fact the interview started normally and ended up with me spending the night with him at his place. We did for 3 years until the business closed and he moved away.

  15. David

    Well, my last four bosses (going back about 20 years) have been women, so… no. Colleagues… not really. But my career has been in university administration, and some of the students – the stuff fantasies are made of. But of course they are off limits for professional reasons, even the few who have openly come on to me. I’ve gotten good at playing clueless in those situations.

    • Danny

      Same here with me. I’ve been working retail and with it’s been with teens– the kind we dreamed of. I to refrain by my own choice for the same reasons you do. I’ve only dealt with a couple who were open with but they weren’t my type anyway felt them a little obnoxious about it. The cute ones who were quieter, I found sweeter and flattering ,but had to play it “clueless” like you did for my own professionalism convictions.

  16. Jade

    I have a few times ,I guess you would call them the boss , I have my own co and a few times when I am doing the work alone I’ve had the customer come on to me .. some were a big surprise and most of them married to women ,but I happen to give awesome head and that’s what these men wanted ,I even still play with a few of them , service with a smile

  17. Danny

    I won’t do it. There’s a fine line. Personally I have little respect for those of either side who practice such crap! The boss for blatantly taking advantage of a person’s necessities ,and the employee for demeaning themselves all for the sake of scaling up the job latter! Now,I know some of you may be taking me for some kind “goody”. Well, one develops that kind of resentment for that if you’ve been affected by persons who were doing such practices. It can screw over people not involved too, the hard working and dedicated workers. In my case I would eventually get wind of what else they’d been up to after some of these person’s quittings/transfers probably because things were at verge of getting a little hairy. Which explained why some managers/supervisors seemed to give the impression of having a cynical or smug edge about them,which was passed off as serious “business attitude”.

  18. Mark

    One morning at the coffee put i mentioned to the gay guy in the office that my wife actually had voluntarily gone down on me over the weekend,which she never does. Well a few weeks later he walked into my office and said “you know that thing your wife went do for you, i would”, i was shocked but blew it off and sarcastically said “oh yeah sure”. The next day he came to my office again and said ” i’m serious, that thing your wife won’t do i would, i’m free Saturday, and here’s my phone number” , as he handed me a paper with his phone number on it, and left the room.
    That night i called a married buddy of mine(who doesn’t know i like cock), and told him.what happened his immediate response was “GO FOR IT). I.knew my wife was working Saturday and the kids were gone to out of town school function, so i thought i might as well go for it. Didn’t see the guy around the office next day until riding the elevator with others so i commented to him, “i am putting a home theatre in my basement, you should come check it out on Saturday if you have time” and hesaid he could do that.
    Saturday morning i called him and we set up.a time, i told him if he had porn be wanted to bring we could watch it. Right before he showed up at the house the wife called and said she would be home early, in about 2hours. It was cutting my play time short but was still doable. Mark got to my house and i tried to play it nervous about how i had never done anything like this before. He assured me discretion, we went to the theatre and put in his movie and got naked. Just as we started to play the phone rang, it was the wife she was leaving work now and would be home in 15 minutrs. I hung up the phone, told him shewas on her way home, grabbed the back of his head and skull fucked him quick and hard and shot down his throat. Then got him.out of the house before the wife could get home.

  19. steamy4u99

    Only happened one time for me. I was scheduled to visit a large client of ours who was having some serious production problems. My boss decided that maybe two of us should tackle this one. Sorting out this particular issue was going to take a few days so we got separate hotel rooms in the same hotel. The last night we were there, we went to the hotel bar after dinner for a few of drinks. He paid for the drinks, turned to me and said, let’s go back to my room and watch the basketball game. Never suspecting anything, I thought sure, why not. I knew he was divorced from his wife, but had no idea he was bisexual as well. With the game on tv, and us enjoying another drink in his room, he blurts out “trips like this make me horny”. I forced an uneasy laugh as I blurted out “I seem to always be horny”. To which he said “let’s do something about that, are you up for it”? My stumbled reply ” I didn’t know you enjoyed naked fun with other guys” . “For years now i’ve been enjoying it” was his response, “how about you”, are you into it”. “yes, for years now” was my response. He leaned over and put his hand on my thigh, as I reached for his cock and balls. Soon we were completely naked on the bed, basketball game blaring on tv as we were sucking each other’s cocks. Before long, I was laying on the bed, pillow under my hot tight ass, legs spread wide and over his shoulders as he drove that 7 inch cock deep inside me. It felt so good. I stroked my cock as kept plunging that nice cock deep inside me. Soon we were both cumming together. We showered together after, and stroked each other off one more time before I went back to my room. We drove home late the next day and I couldn’t help wondering if anyone ever had a connection like this with their boss. Believe it or not, we never did anything ever again. In fact, he took a job with another company and was gone two months later.

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