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Is my Straight Boss coming on to me?

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I work in an office and my boss is this hot, married, middle-aged guy (looks like Tom Selleck - mustache and all). We have this combative banter and tend to get smart-alecky with one another. Oh, and he knows I'm gay.

One time, I was eating a sandwhich, my mouth full and chewing. He walked by, stopped, looked over his shoulder at me, then said in a low voice, "Got room for more in there?" He grinned then quickly walked out the door. I was, like, what was that about. Am I crazy or was that a come-on?

There was such a strange vibe. What do you guys think. I'm pretty sure his wife doesn't blow him. Another time, I handed him some paperwork and said, "I promise this is the last thing I will give you." Then it that low voice again, he said, "I'd be very disappointed."

What do you guys think?
 
There is an old saying, "Never shit where you eat." You eat (make a living) because you work. Don't screw around with the boss. If he is only joking with you, then he may be offended if you make a move on him. Even is he is seriously flirting, when he is through having his way with you, he may fore you because he is uncomfortable having you around.
 
I agree with Homoerectus. Proceed with caution. While this may innocent for now..if someone else picks up on his playfulness and your attention and calls his bluff because your gay and he is married, it could be a loose, loose for you. Fishing may be fun for now but there maybe an alligator in the shallows.
 
or you could get a recorder for your ipod. allow for a 'situation' where he makes a sexual innuendo and record it. listen to the recording to hear if it will hold water in court. then blackmail him for sex and then sue him if things get weird. funny alot of people who know i'm gay joke around w/ my boyfriend and i--and yeah there's the weird vibe. and yes i think he wants to swing bi. a friend of mine (who's straight) told me he would when he was drunk. it isn't going to happen though :)
 
If it makes you uncomfortable, say something.

I wouldn't consider getting involved with my boss, straight or gay.

I worked with a guy for many years who was quite the cutie. We'd always share innuendo back and forth - it was all in jest. There was no way in hell that we'd end up doing anything together for three reasons - he's straight, he's married, he's my co-worker.
 
To be honest, the first joke sounds more like a jibe at the way you were eating or your weight (depending on your body type). The second one sounds like he was making an awkward work joke about productivity.

He may have meant sexual things but my above interpretations show just how wrong you could be -- and that would put you in a sticky situation. I would just keep tight about it and see if he says anything else that could be taken in a worse way. Go from there but I'd go the sexual harassment route before I went the sleep-with-the-boss route. As someone else said, he could fire you if things get weird.
 
There's every chance that you boss is interested in you, scorp. Or at least interested in you blowing him.

A former boss of mine at a job I worked at 15 years ago used to do the same to me. He'd lightly flirt and drop innuendos, but I assumed he was just teasing since he was married and had two kids. One day when we were alone, he pulled his dick out. We've been fuck buddies ever since.

I still don't advise getting involved though. The job I was working at the time was just a summer job while I was in college, so there was no future in it anyway. I would have to think long and hard about doing the same in my current job.
 
Thanks... I will be cautious though. But what a hottie he is. Anyhow, get this... The other day I was in his office, and I was a little distant, and he was saying that I was being "Unfamiliar" and I replied "Would you rather I was overly familiar?" And he said, yes...

Hmmm. Ding?
 
I'd enjoy the flirtation and keep it at that if I were you. This thing could go wrong in so many ways--with you getting hurt in every one.

Suppose he's just teasing; if you show real interest, it puts him in an uncomfortable place and he's likely to get angry or resentful, or lose his respect for you. Things between you will get tense, possibly hostile, which will make your job suck big time. (It will also kill your chances to move up the ladder.)

Suppose he means it. That's even worse. There's no telling how he'll behave after you fuck around with him. But it will certainly change him and things at work.

If he really gets into it, he'll keep wanting more and because you two are together for hours on end, it will turn into an obligation that offers no practical or emotional benefits to you. He'll stay with his wife to maintain appearances; you'll become "the other" and have to be happy to get him when you can, rather than when you want or need him.

If it's a fantasy driving his comments, he'll do the deed but won't be ready to cope with the emotional conflicts it triggers. Maybe guilt, maybe confusion, maybe disappointment (no matter how great you are in the sack), maybe truth about himself--he'll feel something that he's not expected, though. And it will cloud his view of you and your professionalism.

If it turns out great, you'll be squeezed in a box, unable to talk about it at work. That will make you crazy. If not so great, you two will have to pretend it never happened, which will probably lead to distance and anxiety for both of you.

You'll know things about him that will change how you see him, too. How he looks naked, how he behaves in bed, etc. But he's not a trick that you can avoid. He's your boss.

And what if it turns out to be one-sided with one of you thinking it was amazing and the other not so impressed? How do you work around that?

If you like your job, the office atmosphere, your coworkers, etc., you can pretty much kiss all that goodbye... sooner or later.

On the other hand, if you let him flirt all he wants, a strangely exciting bond will happen. He'll realize you're respecting his position and his marriage; you'll get to enjoy attention from what sounds like a damn sexy guy.

Years ago, I was in your shoes. I had this hot, hot married boss--looked like a Kennedy, but with the body of a linebacker--who sent every imaginable signal my way. He'd park in my office for hours, closing the door as he came in and had no business reason for being there. He'd make two-sided jokes, ask me about my personal life, complain about his marriage being at a standstil. He'd rock back in his chair, legs wide open, and watch closely to see if I checked out his package. (I did, of course, and it was obvious he had feast tucked away in his suit pants.) I played along, flirted right back at him, but never indicated I wanted it go further than our little game.

I wanted this man so bad and I probably fell in love with him, too. That's how I realized that if I had him, I'd lose him somehow--and my job would either go sour or go away in the aftermath. As he moved up, he took me with him until I got a great offer from a competitive firm. When that happened, he wrote my letter of recommendation.
 
You're absolutely right. No sense playing with fire.... Besides, I can always just fantasize about him and leave it at that...
 
I am a professor at two local community colleges in our county. Both districts are pretty conservative. Therefore, I am ultra-careful about any interaction with my male students. Gay professors aren't safe these days.

Well, the head of our department comes along and makes a pass at one of my female students. Not once, but several times. What kind of BS is that?
 
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