s it cheating if SHE were to be paying another man to satisfy her (and not telling you about it, and letting you think you were the only one to be intimate with her?)  

Whatever you answer for her, then that's the answer for yourself.

Of course, if you tell her up front, that you're going to be doing the HJ and BF thing , let HER decide if she's okay with that.  Maybe she will be, who knows.   Takes some of the work off of her then that way, as most women stop doing all that once they get what they want from a guy.  (the security of half of everything you own and maybe a few kids to boot)   Why do they care if your'e getting it from someplace else, many are no doubt relieved.
That's how I've always justified it

Hers would be the only opinion that counts if you become a couple. Doesn't matter what opinions we might hold, nor what your personal guilt meter might have to say.  

But have a good long talk with the HR department before you get sexually involved with someone you supervise. It's not just your own reputation at stake, your employer is also at risk if you fuck it up. It might be worth $1K for a one time fucking experience with her, but is it worth your career?

In my opinion, seeing an escort is not "cheating".   Cheating is having a deep, emotional connection to a person other than your SO or Spouse.  Even if you develop a friendship of sorts with the escort, it is not  
cheating.  There is (or should be) no expectations of Love or deep feelings between hobbyist and escort.

Whether the civie lady believes the same is another question and one you would have to ask her feelings about.  I would have the discussion sooner rather than later to avoid hurt feelings.

As for the boss thing............well, that is just asking for trouble and sexual harassment lawsuit waiting to happen

You say she is an 8-9 and we would pay 500-1000 for a one time fuck?  

Tell her she is an 8-9 and offer her the 1k for a fuck and see what happens!  If she takes it and does not punch you in the face, she is probably setting you up for a lawsuit.  The 1k is just a retainer fee for her lawyer.

Most places I have worked fired both employees for fucking around.  

Who knows she just might be an escort and you are a john, how would we know?  This is all for fantasy on this site right!

Btw it is only cheating if she swallows!

...months now. In fact, the last few times you've kissed her you've been sucking my cum off of her youthful pouty lips. Times have changed and it's now OK for a boss to have sex with a subordinate as long as the boss treats the subordinate favorably with frequent pay raises, inflated performance appraisals and paid time off whenever the subordinate asks. Good luck and have fun, buddy. She LOVES side saddle!

You have an intelligent, beautiful women in a professional setting and your sick view of women immediately objectifies her as a source of pleasure, not an equal in the workplace. Even worse, she is an organizational subordinate that you have rank over. Maybe it's the workplace power you have over her that makes this even more enticing.  

Please leave this girl alone and let her become something more than your paramour