I recall the original releases of the game before it was even a paid product having some pretty questionable content. Like I recall you could straight up blackmail one of the girls and maybe knock one out (although that might be completely wrong). There's also the custom story option but I don't think anyone's made anything particularly risque in terms of non-con content, unless anyone here knows of any custom stories like that.
There was a blackmail quest, but it wasn't really as bad as people made it out to be. You couldn't actually have sex if you went down it. You could just strip Madison and send her back to the party, embarrassing her and getting revenge on what she did to her sister. Although there was a bug where if you got her relationship high enough despite it, she would still give you a blow job I think. After the game got popular though the devs re-wrote it into the current quest, which is kind of the same thing because you steal Madison's phone and her nudes and ship them off to a porn director to try to get Madison hired for porn without her consent. For some reason that is an easier pill for people to swallow than direct blackmail.. lmao.
But overall the game was always pretty vanilla. There was never any physical violence like knocking girls out and having sex. In fact, they never even had a route where you could sleep with a girl after getting her too drunk or giving her sleeping pills or anything like some of the other games on here have.
If anything, the earlier versions you were talking about were darker, and included more violence. Like you could kill Frank and Rachael I believe. It was still done in a funny, way, but it was just very dark humor.