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Dilemma

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I'm looking for a little direction here. I'm 23, recently graduated from a really competitive university, and like most of the people in my year, have had some trouble finding a decent job. After school i moved back home and was planning to stay 6 months, earn some extra cash and recover a bit from senior year. Now it's been over a year and I'm still stuck in the same shitty bank job. I also live in the an area with pretty limit social opportunities for your people in general and gays in particular. So after a few months i was getting pretty bored. I posted an ad on craigslist just to see what would happen. It was just a general ad for an NSA hook up. Not really my style but i was getting a little desperate.

One of the replies I got was from an older guy saying that he knew i had posted for someone around my age but he was willing to be "generous." It's not something I had ever considered before but he seemed like a pretty decent guy, just really really closeted and really paranoid about someone finding out. I met him once, and he was so nervous that all i gave him was a handjob after which he offered to "take me shopping." I thought that was weird so I passed and instead he gave me $500 which was pretty nice and also took me to dinner. I found out that he was an executive at Sony and that was why he felt the need to be super discreet. I told him a bit about myself and i think he was surprised that i wasn't some kind of like, professional rent-boy or something. We only met two more times after that but the most he ever did was blow me. However, at our last encounter I mentioned that i was frustrated with my job and my general situation. So he offered to find me a job at Sony.

Now come's the dilemma. I'd actually love to have the sort of media job that he's offering me. However, I'm not sure I really want to build a career on a foundation of prostitution. I was never totally comfortable with the idea of taking money for sex, I did it and I'm not making excuses but it does bother me a bit. The other concern I have is that this offer seems out of character for him. He's so guarded and concerned about secrecy but he's willing to find a job for the twenty-something kid whose dick he sucks. I don't want to pass on an opportunity but I also don't want to end up in a weird situation. Any suggestions you guys have would be helpful.
 
Do you really think it was prostitution? It sounds like you had no expectation of receiving money for sex - other than him mentioning that he could be "generous." That's pretty vague.
It's not like you set a price or gave him a bill or anything. Instead, it sounds like he enjoyed his time with you and gave you a gift. Basically, you didn't charge him for sex, he offered.

The second part is the job offer part. You said you don't want to "build a career on a foundation of prostitution." It doesn't sound like you are trying to build a career off of him or use him. You mentioned your frustrations with your job search. He's in a position to help, and again, he offered his help -- it doesn't sound like you asked him to find you a job.

I think the safest thing to do would be to not accept the job search help and just occasionally see this guy casually when you feel like it.

However, you are stuck in a "shitty bank job" you can't stand, for which you are well overqualified. You also say that the kind of media job he can help you with is what you want.

I kind of think I would take him up on his offer for job search help. A couple of questions though, do you know if you would be working directly for him? Have you talked about any of your concerns with him? (Perhaps this is a non issue to him, and you've built up more of a dilemma than it is.) I think the deal breaker would be if part of your job at his company was to be his on site booty call.
 
Your thread title is perfect--it's the definition of a dilemma, which is the choice between right and right. It's right to want a good career-advancement opportunity, and it's right to feel weirded out by how it all came about.

Your last paragraph is insightful in that it is him that is taking a huge risk by offering to bring you into the company knowing what you know about him. It *probably* is that it is HE who is taking the risk here, though, so keep that in mind.

There are a couple of things to think about and do. First thing to think about is how "out" do you want to be, professionally. Is that a concern for you? If so, then you might want to pass on this. If not, or you're neutral, keep considering.

Second, you'd need to have a heart to heart with him and find out why he's taking that risk, knowing what you do and how he needs to be so discrete. You'd have to have an understanding that there are no "expectations" for a routine thing--that, if you joined the company, you'd need to cut off the physical stuff (otherwise, you're headed toward a career-ruining mess). Even if he promises that, you'd have to use your instincts in whether you trust him, or whether he'd try to blackmail you or sexually harass you (he may not if he has more to lose than you do).

Overall, you're going to need to use your judgment. How much do you trust him? Is the offer firm (how does he just create a position, and fill it without a search or the involvement of human resources?)? Can you trust him not to be obsessed, fall in love, or be otherwise risky? Only you can answer these things, based on what you know. I wouldn't defacto decline just because he blew you and offered you $500 for a handjob. I would, though, want to have some clear understandings and perhaps know him and the situation better before committing.

Good luck. What an interesting problem to have, really. Let us know what you decide to do!
 
You both make really good points. My major concern isn't really that he would expect more from me. To be honest I sort of feel like I have the upper hand in that sense. He's extremely sensitive about being outted in any way. I would never do that to someone but I think it pretty effectively blocks any potential he would have to force me into something. I also don't think it's really in his nature to do that.

My concern, honestly, is that I would be taking advantage of him. He's a nice guy but he's also a bit of a pathetic case. He's an attractive successful guy who's totally unable to come out and as such he's feels like he has to pay for even the most minor encounter. I've already exploited that by accepting cash. The first time was something of a surprise but the second and third it was understood that i was getting compensated. I was actually planning to end it for exactly those reasons until he made this offer. I guess what I'm saying is i'm confident in my ability to control the situation but I'm not sure if I should. Thanks for your input.
 
Why to simply discuss it with him? Say "The job offer is very tempting, and I'd love to have a job like that. My concern is that, at that point, I don't think I could get physical with you anymore. I don't want to appear ungrateful or anything, but if I took the job, I'd have to call an end to doing anything sexual with you. I want you to understand that, and I'll understand if that makes you hesitant to leave the job offer on the table."

Lex
 
You're right that that physical aspect of the relationship would have to end. Any scenario in which I take this job would definitely involve making that clear. I do still have reservations about taking a position like this when it would be the direct result of me hooking up with this guy. I should also point out that I wouldn't be working directly with him but I would be in a division that he oversees. Essentially he'd be my boss's boss. It's a relatively junior position but unlike what I'm doing now it would be a job with a future. I'm leaning toward taking it but I still feel like a creep.
 
I wouldn't feel creepy about it so long as everything was on the table. If you took the job without talking to him, which would suggest that the sex would continue, yeah, that's creepy. But if you make everything clear, and the job offer still stands (to wit - he doesn't seem crushed by your words), then I'd say it's more of a case of "he finds you to be a nice guy and is willing to do you a good turn". Besides, a job isn't like being handed money. It's a two-way proposition. You provide work in exchange for the money.

Lex
 
just ask him directly what the job offer really means. Tell him your concerns and let him get it straight. You don't actually have the job now, and it's nothing else than a chance you MAY have, then you sill have nothing to lose.

good luck.
 
I think he's the one with the dilemma more than you. And he's being foolish by going through with this. With his behavior he's going to be outed sooner or later. If he's so closeted he shouldn't be mixing work and super discreet pleasure. And he may have the expectation of messing around wtih you after, as others said, clear that up.

Well, why not take the job, you do have the upper hand, don't feel like a creep, look: How many young women (and men) who have risen up in corporations or become famous actresses did so through a little messing around at first? Ever heard the term "who did you have to blow for that?" Or I guess in your case, get blown, which is, easier :)
 
Question #1 is, "Do you want the physical relationship with this guy to end?". If you want to continue seeing him- whether it be as a fuckbuddy, a friend or a sugardaddy, then you can't work for him.

Question #2 is whether you could get this job and keep it on your own terms. You have a degree. Presumably, you have a stable work history. Is this a job that you can obtain and retain on your own merits and competencies? The problem is that if someone hires you on a whim, they can fire you on a whim.

Have a talk with him. It's fine if he opens the door for you to get the job on your own. If he's telling the hiring manager to hire you even though you're not qualified, then that's probably not a situation that you want to get into.
 
The answer to your first question is no. He's a nice guy but he's no someone I'm really attracted to. There are a couple of reasons not that least of which are the age difference and his extreme closetedness. I don't publicize the fact that I'm gay in a professional setting but my friends know and I don't think it's wise or even possible to have a real relationship with someone who is that committed to secrecy. As I said i had more or less decided to end our existing arrangement after our last meeting. However in the course of a conversation he presented me with this offer.

As far as your second question, i do believe the job itself is something I can do. Without going into too much detail it's a real position that I feel would be appropriate for a new hire. It's not just a fabricated position for a paycheck I wouldn't really be interested in that. It's definitely in my field and it's something that I am eager and able to do. As to whether I could land the job without his assistance, I suppose it would be possible. However, things are extremely competitive right now. This would essentially be a sure thing rather than a 1 in 100 shot.
 
Given your answer to #1, then there's nothing preventing you from taking the job.

And given your answer to #2, then apply for the job. Leave it up to your friend as to whether he wants to put in a good word for you but make it clear that if he does, there will be no bartering for sex in exchange.
 
I want to thank you all for your input. It's been helpful to have a neutral sounding board for this problem. After considering your comments I decided that I'm going to accept the offer on the condition that there are no physical requirements. I'm still wary of complications and I think it might be an ethically questionable move but I think it's a chance worth taking. I want to seriously thank you guys for the input. I'll definitely let you know how it goes. I stumbled onto this community and joined up just to post this question but I've enjoyed poking around over the last couple days and I think I'll likely become a semi-regular contributor to these forums. See you around!
 
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