Should I fuck my boss?

[snapon]

So here is goes. I do a lot of accounting/computer work for my boss on his home computer, and while searching for a file I downloaded I came across some gay porn. This peaked my interest, so I looked though his computer history (shady I know, but I need to know what I was getting into) and I'm glad I did. He had a couple searches in the m4m section of craigslist, and he has been meeting with an escort which he pays, although I'm not sure how far they go or how often. He is closeted as far as I know, as well as myself.

Here's the deal. I am 21 and have never been with another guy, but I really want to and I feel like this is the perfect opportunity. He is 53, bear type which I am attracted to. I am not really attracted to guys my own age, and have always been to afraid to meet a random hook up from a4a or craigslist. The positives are that I'm sure he is discreet, which I would like as well because alot of people I know know him as well, and I am not ready to come out. This is actually like the first time I have actually been about to do something with another guy. However, some of my concerns are how safe he plays with his other hook ups (from what I saw, it was only the one guy for the past few months) and how it will affect my job. I am not looking for a relationship, I would really just like to try stuff with a guy and see where it goes. Fwb would be what I;m looking for if I do enjoy it, if I go through with it.

Anyone have any advice whether or not I should try something? How should I go about it? Any advice is greatly appreciated!

 

[looseliam]

I'm with Bender, but let me put it another way: FUCK NO!

 

[snapon]

:/ Ah well, guess it's for the best

 

[hylas]

bad idea. unless getting another job when things go south is easy for you.

 

[snapon]

It is not my main job, more like a on the side thing. However, with my prior apprehensiveness and the negative reponses, I probably wont.

 

[racer2438]

Never mix sex in thw work place....unless your planning on looking for a new job soon.

 

[ryanboy]

Not a good idea to shit where you eat. But if lust gets the better of you, at least get a pic of the event for job security. Good luck dude.

 

[Rolyo85]

Yeah, not a good idea. Also, you have no excuse for roaming into his personal files.

 

[ryanboy]

Rolyo85, I follow a lot of your thread replies. I like how you think and you seem like my type of guy.

Yeah, not a good idea. Also, you have no excuse for roaming into his personal files.

 

[Orlandude]

NEVER dip the pen in office ink. You are simply setting yourself up for the worst. Nothing is worth jeopardizing your job...especially the way things are these days. I've seen this happen so many times and it never ends up good.

 

[Rolyo85]

Rolyo85, I follow a lot of your thread replies. I like how you think and you seem like my type of guy.

Glad to help

 

[chub23lauderdale]

Not a good idea to shit where you eat. But if lust gets the better of you, at least get a pic of the event for job security. Good luck dude.

I was just going to say the same thing

 

[Seasoned]

My question to you is this. Are you going to be able to stop yourself from searching through his history file in the future? If not I'd drop him as a client. You have a job with a lot I'd security and sensitivity issues. You need a reputation and you need trust and discretion to do the job you do. Tread carefully. Whether you're ready right now or not begin to think about coming out. The problem with secrets is that they cause clandestine behavior which can be highly addictive and affect your life even after you come out. Take care.

 

[snapon]

It is not a legit job job, basically hes a friend of a friend that I help out and get paid under the table. Nothing corporate about it. However, I understand the concerns and I have no intentions of looking again as there is no reason to.

 

[jaysizzles]

in that case, I say go for it. How you go about getting his attention/ come on to him while remaining in the closet and not tipping your hand that you pilfered through his computer and seen his porn stash is another matter now...

 

[Seasoned]

It is not a legit job job, basically hes a friend of a friend that I help out and get paid under the table. Nothing corporate about it. However, I understand the concerns and I have no intentions of looking again as there is no reason to.

I'm happy you've cleared the air for yourself. Do take care. I hope you'll be out of the closet one day and further hope that day is not too far off. Best wishes.

 

[Just_Believe18]

Glad you came to your senses with the good advice you received here.

 

[HunterM]

No, you shouldn't fuck your boss. But I would like to. Tell your boss to call me.

 

[snapon]

in that case, I say go for it. How you go about getting his attention/ come on to him while remaining in the closet and not tipping your hand that you pilfered through his computer and seen his porn stash is another matter now...

He walks around without his shirt on all the time for no reason, and I catch him checking me out when I adjust my boxers/pants.

I'm happy you've cleared the air for yourself. Do take care. I hope you'll be out of the closet one day and further hope that day is not too far off. Best wishes.

Thanks

 

[jaysizzles]

He walks around without his shirt on all the time for no reason, and I catch him checking me out when I adjust my boxers/pants.

Then adjust away...catch his gaze, smile, lick your lip, adjust yourself again...send him signals that you are receptive. If he doesn't jump at that, then he ain't gonna.