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  Should I sleep with my boss?
ConfusionAnonymous writes: I have been at my current job for 3 months and during that time my attractive female boss has been flirting with me. She is distant with my co-workers but she laughs at everything I say and blushes whenever I tease her. She has "accidently" touched my hand several times and always moves closer to me when she wants to talk. My fear is that maybe her signs of attraction are just me seeing things that might not actually exist. If she doesn't really like me, (she has mentioned her boyfriend)and I make a move, my job could be greatly affected. What should I do?

Boy, we all know how tempting a situation like this is! Here you are forced to spend hours a day with an attractive woman who happens to be flirting with you and who happens to have a boyfriend... Does it get any better than this?

Well unfortunately, sleeping with the boss, even when it goes well, is really not recommended. Basically you have to decide whether the job is worth more than a dalliance (or even a relationship.) If you want to keep your job, you'd best just keep things at a flirting level. And if you want to keep the relationship with your co-workers good, keep the flirting discreet and private. All is not lost, secret flirting can be quite fun in itself, especially to liven up a boring workday.

OK, so what if you really want to sleep with her, job be damned? Well, if you ever get her in a social setting, in the evening, have a meal, a few too many drinks, things might just happen. And then you can both chalk it up to one night of alcohol-fueled passion and put it behind you.
Posted on Thursday, 16 September 2004 (11:01:51) UTC by gfs

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Re: Should I sleep with my boss? (Score: 0)
by Anonymous on Tuesday, 15 November 2005 (04:26:43) UTC
I am highly attracted to my female boss (I'm male). She is the CEO and I have worked with her for three years. We have a strong professional relationship but due to spending so many hours a day together for so long we have a low key mutual care and understanding. I am 33, she is 41 and every bit the professional. I am in awe of her intelligence and gladly do whatever she tells me because I know how smart she is. Her dominance over me has built within me a yearning to serve her and be dominated by her. She is aware of my feelings about this from years of very subtle hints and I feel that she also thinks about dominating me in the bedroom and would go there if it wasn’t for her professionalism. After subtle hints, for so long, I’m just about at my whit’s end. I could live without the job, to me the loss of the job would be worth the experience and I believe it would work out well anyway. I want to find a way to come clean and just let her know what I think about her, and doing to her and for her. Coming right out is just not going to work. She needs to be assured of my confidentiality, that it would never under any circumstances either interfere with work or be repeated to a single living soul. My word on this would carry a lot of weight with her. She also needs to be sufficiently motivated funually, I need to turn her onto the idea. Get her thinking about it. Probably my biggest fantasy is to have her tell me to eat her and then to comply. I think if I could plant that seed, over time, it would probably grow into something I could work with. After all, what single 41 year old woman does not find receiving oral fun from a nice looking, nice, trusted guy ten years younger not appealing, especially when you consider the subtle seeds of arousal I have already sown over the past three years ? I had one idea about asking if I could put my personnel laptop in her office and leave it there for a few weeks with no password and a large obvious file with her name on it. In that file, I could put this nice naked picture of myself (I’m sure she would like it and find it a turn on) and a letter about everything I would like to do with her and for her. I was thinking about a hypothetical email she was never going to be sent kind of format. I should be safe because she should not be opening my computer and snooping and also be getting my message across. I think the chances of her looking at it some time in two or three weeks would be quite high. I would of course install a key monitor before hand so I could tell if it had been opened.. So what do you think ? got a better idea ? have any improvements to my plan ? What’s your take ?

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