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  1. #1
    Virgin snapon's Avatar
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    Should I fuck my boss?

    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!

  2. #2
    Vilified Poster. BENDERBOY's Avatar
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    Re: Should I fuck my boss?

    I'd stay well clear if you value your job.

    There are millions of other guys you can get with.
    "You may only be one person to the world, but you may also be the world to one person"
    - anonymous quote.

  3. #3
    aww I wanted to explode looseliam's Avatar
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    Re: Should I fuck my boss?

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

    Give a man a fish, he'll eat for a day.
    Give a man religion, and he'll starve praying for a fish.

  4. #4
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

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

  5. #5
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    Re: Should I fuck my boss?

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

  6. #6
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

    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.

  7. #7
    JUB Addict racer2438's Avatar
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    Re: Should I fuck my boss?

    Never mix sex in thw work place....unless your planning on looking for a new job soon.
    You cant change the way the wind blow's, but you can change the angle of your sail to take you somewhere else!!

  8. #8

    Re: Should I fuck my boss?

    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.

  9. #9
    Impish and Mercurial Rolyo85's Avatar
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    Re: Should I fuck my boss?

    Yeah, not a good idea. Also, you have no excuse for roaming into his personal files.
    That we are capable only of being what we are, remains our unforgivable sin.
    - Gene Wolfe

  10. #10

    Re: Should I fuck my boss?

    Rolyo85, I follow a lot of your thread replies. I like how you think and you seem like my type of guy.
    Quote Originally Posted by Rolyo85 View Post
    Yeah, not a good idea. Also, you have no excuse for roaming into his personal files.

  11. #11
    JUB Addicts Orlandude's Avatar
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    Re: Should I fuck my boss?

    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.

  12. #12
    Impish and Mercurial Rolyo85's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by ryanboy View Post
    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
    That we are capable only of being what we are, remains our unforgivable sin.
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  13. #13
    On the Prowl chub23lauderdale's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by ryanboy View Post
    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

  14. #14
    Coward92
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    Re: Should I fuck my boss?

    Quote Originally Posted by ryanboy View Post
    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.
    How can you possibly even compare something as sensual and wonderful as sex to shit?

    To the OP: Just dont.

  15. #15
    I'm now a grandfather! JUB Moderator Seasoned's Avatar
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    Re: Should I fuck my boss?

    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.
    Last edited by Seasoned; February 6th, 2013 at 11:39 AM.
    "Be who you are and say what you feel because those who mind don't matter and those who matter don't mind."--Dr. Seuss

  16. #16
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

    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.

  17. #17

    Re: Should I fuck my boss?

    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...
    Bad decisions make good stories.

  18. #18
    I'm now a grandfather! JUB Moderator Seasoned's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    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.
    "Be who you are and say what you feel because those who mind don't matter and those who matter don't mind."--Dr. Seuss

  19. #19
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    Re: Should I fuck my boss?

    Glad you came to your senses with the good advice you received here.
    #439th oldest member on JUB.

  20. #20
    JUB Addict HunterM's Avatar
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    Re: Should I fuck my boss?

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

  21. #21
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by jaysizzles View Post
    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.

    Quote Originally Posted by Seasoned View Post
    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

  22. #22

    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    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.
    Bad decisions make good stories.

  23. #23
    vvaamim
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    Re: Should I fuck my boss?

    Don't shit where you eat. It never turns out well.

  24. #24
    GiancarloC
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    Re: Should I fuck my boss?

    In all honestly, no WAY. Keep the job... even if it isn't your primary work. The economy still isn't great, so I would be happy to keep the job and not put it in jeopardy. And who knows... it might mess up future work opportunities too.

  25. #25

    Re: Should I fuck my boss?

    Sex complicates any relationship, even the very best one. I've succumbed to the temptation twice in years past. Both instances resulted in the loss of the job, not to mention you have no reference and you just don't know what people are saying about you behind your back.

  26. #26
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    Re: Should I fuck my boss?

    So I am getting my shit together. I am going to just let it be, act as usual. Not sure what to do if he comes on to me? Being a virgin who is really ready not to be, I'm not sure I could resist. However, I plan on coming out to one of my better friends on saturday when he comes home from college. I hope this is the right decision, i don't think he will have a negative reaction but I don't know about my other best friend. We have known each other since we were three years old, but he has said on multiple occasions that he "hates" gay people, but never gave a reason. Sorry for the rambling, just thinking out loud.

  27. #27
    I'm now a grandfather! JUB Moderator Seasoned's Avatar
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    Re: Should I fuck my boss?

    It's not a ramble. Good luck this weekend! As for your other friend, if he truly hates gay people, which might be more bravado than fact, you've already done your share of tiptoeing. The tide has turned. It's homophobes who are now the outcasts in forward looking circles. He has more to explain than you.
    "Be who you are and say what you feel because those who mind don't matter and those who matter don't mind."--Dr. Seuss

  28. #28
    Sex God AngolaZee's Avatar
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    Re: Should I fuck my boss?

    What if he was hoping you would discover the files. I mean i have porn but i lock it with TrueCrypt to make sure even the FBI wold never find it. To make you work on his computer (without his supervision) is a little bit odgy. Either way better stay clear unless he comes on to you

  29. #29
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    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    I plan on coming out to one of my better friends on saturday when he comes home from college. I hope this is the right decision, i don't think he will have a negative reaction but I don't know about my other best friend. We have known each other since we were three years old, but he has said on multiple occasions that he "hates" gay people, but never gave a reason. Sorry for the rambling, just thinking out loud.
    hi Snapon,

    Good to read that you have decided to come out to one of your better friends. I tend to think that this is right now (you are 21 years, and I assume he will also be around your age) a good moment to tell him the truth about yourself. So I would like to wish you good luck. I hope he will react on a positive way, and that things will not change alot when he is aware that you are gay. Well, I even predict that the friendship between you and him will improve, as right now he does not have a real idea why you don't have a girlfriend, and why you don't seem to be interested in girls.

    When things go well with him (and I am expecting that this will be the case), then there is the other guy. Well, real homophobes cannot be friends with gay guys, that's out of the question. So either he will excuse himself for all these homophobic ideas / opinions (or consider them as outdated, or bad informed, or whatever) and he will stay good friends with you as soon as he becomes aware that you are gay. Or you must decide that he not a 'best friend', and thus must decide to stop with being friends with him.

    Friend A (first one you want to out yourself) and friend B are aware of each other? You might also discuss this topic (the reaction of B) with friend A, after you have told A that you are gay?

    Anyway, I would like to wish you good luck by telling him that you are a gay guy. Take care.

    Feel free to react and/or ask addition questions.
    I am Dutch, so please excuse me for my low level of English.

  30. #30
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by AngolaZee View Post
    What if he was hoping you would discover the files. I mean i have porn but i lock it with TrueCrypt to make sure even the FBI wold never find it. To make you work on his computer (without his supervision) is a little bit odgy. Either way better stay clear unless he comes on to you
    Perhaps. He is very computer illiterate (why I do his computer work) so I don't think he knows that that kind of stuff is saved in the download folder, much less how to hide it. But who knows, maybe he is the one throwing me for a loop and setting it up. Either way, I am not going to pursue it any further, it will be up to him.

    Quote Originally Posted by Ganoderma View Post
    hi Snapon,

    Good to read that you have decided to come out to one of your better friends. I tend to think that this is right now (you are 21 years, and I assume he will also be around your age) a good moment to tell him the truth about yourself. So I would like to wish you good luck. I hope he will react on a positive way, and that things will not change alot when he is aware that you are gay. Well, I even predict that the friendship between you and him will improve, as right now he does not have a real idea why you don't have a girlfriend, and why you don't seem to be interested in girls.

    When things go well with him (and I am expecting that this will be the case), then there is the other guy. Well, real homophobes cannot be friends with gay guys, that's out of the question. So either he will excuse himself for all these homophobic ideas / opinions (or consider them as outdated, or bad informed, or whatever) and he will stay good friends with you as soon as he becomes aware that you are gay. Or you must decide that he not a 'best friend', and thus must decide to stop with being friends with him.

    Friend A (first one you want to out yourself) and friend B are aware of each other? You might also discuss this topic (the reaction of B) with friend A, after you have told A that you are gay?

    Anyway, I would like to wish you good luck by telling him that you are a gay guy. Take care.

    Feel free to react and/or ask addition questions.
    Thanks for the support, I really appreciate it. Friend A is actually coming home today but I am not sure I am ready to bring it up. I was sure about it yesterday that I was going to, but now that it is coming closer I am just feeling a lot of mixed emotions. Part of me is afraid (not sure of what) and the other side KNOWS that this is the situation, and holding it in further is just going to make things worse in the long run. I guess I just gotta stop being a pussy and get it over with. After the initial "outing", does it get easier? With friends at least, parent's and family is going to be a whole other issue.

  31. #31
    Virgin snapon's Avatar
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    Re: Should I fuck my boss?

    Well, I was hanging out with both friend A and B tonight. While we were hanging out, Friend B was trying to hook me up with some chick he met (this doesn't happen often). I kinda went along with the oh, thats cool, but trying to dodge any commitment but they kept pushing. I was at the point where it was really getting to me and I was just about to blurt it out (don;t think this would have been good) but in the nick of time I recieved a phone call and they ended the discussion after.

    I will be hanging out with friend A tomorrow by himself, and I am going to do it. Wish me luck.

  32. #32
    PerScientiam AdJustitiam bankside's Avatar
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    Re: Should I fuck my boss?

    I wonder if his last escort also started by working for him as a computer tech.

    "Oh no! I'm so embarrassed! I didn't mean for you to see my entire 4 terabyte collection of "Bear on Twink Action Videos." Oh I'm so embarrassed! Will you show me how to clear my cache? I'll pay you extra for it. I want you to clear it alll…..clear it deeeep…oh my god i think i'm cumming…."

    Your first experience?
    Americans need to keep their guns so they can protect themselves from gun violence just like Nancy Lanza did. And like Chris Kyle did. And like Gabby Giffords did. And like Tom Clements did. And like Michael Piemonte. And Joseph Wilcox.

  33. #33
    JUB Addicts Dobson73's Avatar
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    Re: Should I fuck my boss?

    110% agree. A major no-no to do what you've done. And nope, probably one of the worst ideas you've had this week. Let him be who he choses to be.
    Quote Originally Posted by Rolyo85 View Post
    Yeah, not a good idea. Also, you have no excuse for roaming into his personal files.

  34. #34
    JUB Addicts Dobson73's Avatar
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    Re: Should I fuck my boss?

    Sorry, Safari issue and two replies at one.
    Last edited by Dobson73; February 9th, 2013 at 02:38 AM.

  35. #35
    JUB Addicts Dobson73's Avatar
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    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    So I am getting my shit together. I am going to just let it be, act as usual. Not sure what to do if he comes on to me? Being a virgin who is really ready not to be, I'm not sure I could resist. However, I plan on coming out to one of my better friends on saturday when he comes home from college. I hope this is the right decision, i don't think he will have a negative reaction but I don't know about my other best friend. We have known each other since we were three years old, but he has said on multiple occasions that he "hates" gay people, but never gave a reason. Sorry for the rambling, just thinking out loud.
    Good on you and good luck. I'm in a different time zone so not sure if you've done this yet. It's an incredibly brave and empowering thing that we do; to tell another human being that we're not what they see and it may challenge every fibre of their being. But it also challenges every fibre of our own being to face someone you love, eye to eye, and say "I'm not who you thought I was".

    I wish you well, my friend and all power to you. After the first comes many, many people and each step is so much easier. You will very quickly learn that the people who care love you and among them will be "The One"!

  36. #36
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    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    Well, I was hanging out with both friend A and B tonight. While we were hanging out, Friend B was trying to hook me up with some chick he met (this doesn't happen often). I kinda went along with the oh, thats cool, but trying to dodge any commitment but they kept pushing. I was at the point where it was really getting to me and I was just about to blurt it out (don;t think this would have been good) but in the nick of time I recieved a phone call and they ended the discussion after. I will be hanging out with friend A tomorrow by himself, and I am going to do it. Wish me luck.
    hi Snapon,

    Thanks for the update and for your friendly reply. Yeah, I think you should stop with being a pussy. So just tell friend A that you prefer guys and that this was the reason why you gave such a lousy reply when friend B (and A) were pushing you to get in contact with that girl. By telling this to him, you don't need to stay hiding this kind of things to him anymore. I mean, A and B will keep wondering why you are not interested in getting a girlfriend, and likely they don't understand your lousy excuses. Maybe (who knows?) both might have already some clues why you don't want to hook up girls?

    I cannot predict for sure what will happen and how B will react when you tell him that you like guys. On the other hand, you are living in the US and its right now 2013. The general opinion about gay people is changing alot and I would like to remind you to what Seasoned told you
    The tide has turned. It's homophobes who are now the outcasts in forward looking circles. He has more to explain than you.
    Finally, there is only one way to go on and that's telling them the truth. Right now, you are -more or less- lying to them (= don't tell them the real reason why you don't want to hook up with that girl), and you must realize yourself that you will need to ly (hide) more and more in the course of the time (as long as you don't tell the truth to them). So better tell them now, and see how they react. I mean, how do you see the future when you will get in contact with other gay guys? Do you also want to hide this kind of information to your best friends? Good friends (= straight guys who are long-term friends) of a gay guy understand very well that gay guys will also have gay friends.

    So please don't be a pussy and tell friend A the real reason why you did not wanted to hook up with that girl.

    I would like to wish you good luck and please keep us informed.

    Best wishes & take care.
    I am Dutch, so please excuse me for my low level of English.

  37. #37
    JUB Addict Ninja108's Avatar
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    Re: Should I fuck my boss?

    No,because at the end of the day,he's in a position of power over you. Never good in a relationship.

  38. #38
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    Re: Should I fuck my boss?

    Quote Originally Posted by snapon View Post
    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!
    No because if anything goes wrong he can retaliate by firing you for any number of reasons and you wouldn't be able to prove anything. Then you would have no job and no reference from him. Has this happened? You bet!
    Your post comments are forwarded to the CIA.

  39. #39
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    Re: Should I fuck my boss?

    Discreetly for a raise, but their are a lot of ppl that will hook up with u sexy man

  40. #40
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    Oct 2011
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    Code of Conduct

    Re: Should I fuck my boss?

    Quote Originally Posted by cgymike View Post
    No because if anything goes wrong he can retaliate by firing you for any number of reasons and you wouldn't be able to prove anything. Then you would have no job and no reference from him. Has this happened? You bet!
    Quote Originally Posted by Ninja108 View Post
    No,because at the end of the day,he's in a position of power over you. Never good in a relationship.
    Quote Originally Posted by kibashyho View Post
    Discreetly for a raise, but their are a lot of ppl that will hook up with u sexy man
    Not sure if you guys have read the thread, it has moved far past this...

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