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Hey, thanks for replying!

So I tried this, via another servant, just to test out the theory. The result was them gaining the "Masochist" and "Likes it Rough" traits. Nothing on "Advanced Sexual Actions" yet, however, I decided to poke further and place her into the Exotic Whore job with the traits she has (She also got the "Pervert" trait beforehand) and the Job Report went without problems, she got paid in full and the boss lady down at the Brothel didn't say anything about customers not liking her and halving the payment. So I think this might be it, gonna do another test with the servant I first encountered this situation with, as I used my Starting Servant for my test and she had some pretty good stats to begin with. 

For that job, they need to have over 45 lewdness or their gold will be halved, that's specifically what will cause it to say they had insufficient skill. So advanced sexual actions is mainly just being super lewd. However, doing kinkier stuff with them causes their lewdness to go up faster.

Then there are bonuses from Sex-crazed, hollow nipples, augmented tongue, and nympho.  Nympho also lowers the stress gained (or if they're a bunny).