Have You Ever: Fantasized About Your Boss?

It’s going to get awkward if I keep writing posts like this. Nevertheless, I can’t just sit here and ignore that people fantasize about their bosses, supervisors or other authority figures! Call it unprofessional if you’d like, but that’s what a lot of guys get off on—the taboo nature of the power dynamic. The forbidden fruit. Whatever you want to call it.

Maybe you’ve thought about bending him over your desk, paying him back for all the nights he kept you late at the office. Maybe you wish he’d call you in, unzip his trousers and fuck your face like a worthless bitch. Or perhaps I should stop coming up with scenarios, so you can leave comments about your own naughty dreams and desires…

– Dewitt

Photo credit: Men Hard At Work

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11 thoughts on “Have You Ever: Fantasized About Your Boss?

  1. boss: no – never had a hot boss
    coworkers: like crazy!  have had some seriously intense crushes and fantasies about coworkers

  2. Years ago in Florida I had a boss who looked a bit like porn star Max Grand–Latino, tall, muscular, handsome face, salt and pepper hair, good dresser…

    He was a great boss and a nice guy, too.  Unfortuantely, he was constantly having to clean up management’s messes.  Many a night after work he would vent to me, sometimes angry, sometimes sad and overwhelmed.  It probably crossed the line between what a supervisor and a subordinate should share, but I appreciated the platonic friendship that developed.

    Besides being my boss, he was straight and engaged, so I never acted on my desires, but GOOD LORD, the fantasies I had about walking behind his chair one night and giving him a slow, deep shoulder rub, then getting down on my knees in front of him, unzipping his dress pants, and making him “feel better” in a way his girlfriend couldn’t even begin to do.

  3. Never had a hot boss, but I’m crushing hard on a current coworker. He def str8 though cause we’ve gotten so drunk together so many times which have ended with me crashed on his couch half dressed that he could’ve had me any of those times, but alas nothing 🙁

  4. hm.

    no bosses come to my mind.

    (besides.. ..most of them, i’d never really been much a fan of.

    in considering their scruples.

    {specifically, the lackings, thereöf.})

    ..well, one gentleman (who was a pretty-recent acquaintance, actually) has just come to mind: he is “management,” and when i worked at his department, i was, indeed, under his jurisdiction of control.
    although, functionally, he wasn’t really my boss.

    anyway, he was very approachable (which always confuses the hell out of my gaydar.. ..that is already limited in functionality as it is), and very cute.

    a bald-headed italian, maybe 36, who appeared to be reasonably in-shape, and about 5’9″.

    if he had said “the word,” we would have been 6-9ing instantly.

    but, alas…..

  5. Hell yea I’ve thought about my bosses. I think it is a power thing, because I’m not even a bottom, and every time I have a male boss, I just want to get fucked.

  6. exmilman


    Make an anonymous call from a payphone to him in his office (make sure it’s him!) and proposition him saying that you’d like him to fuck you coz you think he’s hot and you want to arrange a place/time.
    Make it a quick call, then hang up to give him some time to think about it.
    Don’t let him say anything.
    Then call back later on.

    (Maybe use some cloth or something to muffle your voice)

    If he accepts, and you arrange a place/time, then when you meet him there, let him know it’s purely for sex and you don’t mean to climb the ladder or something.

    If he denies you, you save yourself humiliation & possibly your job.

  7. yes i had hot boss nice and friendly. dress well sometimes i though he was gay ,althought he is married. the way he used to talk to me made me think he likes me.

  8. I used to work in a kitchen and in the kitchen there was a window to a laundry room where my boss would often go in to change. I would love to see it when he was in getting changed and be stripped down to his boxers!!! It also helped that I used to play football with the same boss and often after matches he would be stripped off completely!!! He was quite large!!! 🙂

    But then I got a new job, and my boss gave up playing football!!! 🙁

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