Job w guy who fucked you

[sinfuljock]

So I have interviewed for and am likely to get a job working for an older (40s) man who fucked me at a pool party last weekend. After he did we talked while everyone was recovering and he mentioned he was looking for a new personal assistant which is what I currently do. This new position under him would pay significantly more than my current job and have extensive travel.

Based on the interview and activities after, it's pretty clear he expects the sexual aspects to continue as well. I have no problem with this and find him very hot, but wonder if anyone has a different opinion that isn't as biased in favor of taking a big dick up my ass. So what are your thoughts?

[melvin0095]

What happens when he finds a new assistant in 6 or 8 weeks?... and we both know he will.

[seaguy]

Is it going to be a real job where you are paid legit not under the table? I agree with Melvin0095 though. Sleeping with the boss is not really wise cause when things go bad which they usually do in situations like that your going to be the one who suffers and if you need your job to pay rent bills etc. I would not want to be in that situation. Unemployment sucks I am on it right now.

[NLbear]

I would agree to keep work and play separate. It sounds good to have a big raise and travel around but, as you said yourself, he expects the sex to continue. If anything happens in that area (either he becomes tired of you or you are no longer comfortable with this side of the job) then you're out. Would you be free to roam around or does he expect you to have sex with him only?

If you are satisfied with your current job and it feels secure stay where you are even if it pays less.

Of course, when you feel your current job is not secure or you don't like it anymore you may give it a shot. But my gut feeling is you would be looking for a new job in a few months time.

[barehole4use]

Always better to keep work & play separate even is he is hot as you say, you might regret making a decision like that in the long run.

[Whitebutt]

There's an old saying: don't dip you pen in company ink. And he should know that, or maybe he owns the company and thinks he can do what he wants. I had a long career in management and always kept my dick in my pants. Maybe boring, but then I never had difficulties getting laid outside my work. My advice: don't do it! It's bad for both parties. You will be at a disadvantage, and the day he needs to fire you, the relationship will be a problem for him also.

[rawTOP]

If you think your current job is ending, or you're unemployed - sure go for it. Or if you can do it part time in addition to your regular job - no problem there. But I'm with the other guys - don't quit a solid job for what might be temporary.

[Guest GoodExercise]

@sinfuljock, is he going to keep you on PrEP?

[Deaner]

With ANY job interview, the employee gets to ask questions, just as the employer does. This is something you should have brought up with him already (but DEFINITELY should if/when he offers you the job). It's as important and reasonable a question as asking what your salary will be.

There have been many jobs that I applied for where I knew the company or position had a high turn-over rate (people quitting or getting fired frequently). When you bring this fact up, you can often get the answer that will decide for you. If you bring up the issue that he may 'tire' of you in a matter of weeks or months, you may be able to read his response to see if he truly would keep you longer even if the novelty wears off. Asking how often he has to replace his assistant will let you know if he prefers long-term commitment to the job, or if he considers his employees to be disposable.

Lastly, finding out what qualities he considers to make a successful assistant (and demonstrating those qualities) may help you become invaluable to him in other ways, even if the sex cools off.

I wouldn't write this opportunity off completely, but go into it with your eyes open and well informed.

[seaguy]

@sinfuljock, is he going to keep you on PrEP?

If the position provides medical benefits those kind of decisions are not up to supervisors but would be up to the insurance plan would be something that can't be just changed whenever.

[sinfuljock]

The insurance will still cover PrEP, and his previous assistant is still at the company but has just been promoted. From what I understand they dated for a while while he was his assistant, but have been broken up for several years.

[melvin0095]

Sounds like a better deal now.

[FJLinNYC]

As long as its on the up and up, a real job with benefits. I work at a very large company, more than of the people I work with met their partners at work. So they all started fucking before they married at some company function lol.

[seaguy]

I take it the company does not enforce or have a no fraternization policy. lol

[sean_alan]

Take the job. Get laid. Worst that can happen is you are job hunting again with a great story and a great lawsuit. Or a good job and a great sex life. Live it.