I mean, isn't that what makes it hot though? Part of the kink is that an unattractive fat old dude gets to have fun with someone as hot as Jessica, at least that's what makes the kink hot for me. So yeah, pretty sure having the guy be not sexy is the "sexy". Same deal with Mr. parker.
I agree with you, there are many kinks from it, the difference in attractiveness, the age difference, the fact that she left her boyfriend waiting downstairs while she is having fun with the mayor, the lust within the power, her way to improve her career with the mayor and the senator. It's as you said, the same deal with Mr. Parker or the private detective and perhaps even the senator...it's the sluttiness and cheating while still looking and behaving with class that makes it even hotter.
That's why in
MY playthrough, my focus is for Jessica on the slutty route, flirting and messing her way around with Christian (but not Heather, My Jessica is
NOT a lesbian nor Bi), the mechanic, the editor of the newspaper, the policeman, the principal, the P.I, the kid in the bathroom stall, the Mayor, and possibly the senator. Then, there are the
more individual paths mainly with Mr. Parker and also with Tommy (with other hot kinks when it comes to Jessica & Tommy) which both paths are
my favorites in the game, and after the recent update, the mayor's path too.
I'm aiming at some point for Jessica to break-up with Conner (as
stoper mentioned in one of his posts earlier that it could be possible through choices or consequences, I think) but in the meantime, unless it's absolutely forced like it was at the beginning of the game, Jessica is not having sex with Conner anymore (or ever again) and getting her good times with someone else.
(The same deal in AWAM, Sophia is not having sex with her husband since she arrived in San Alejo and just focusing mainly on her son with just some filthy interactions like the Prison event).