I was having an "bad-ending" idea for my planned game, but seeing that I will probably never been able to finish my demo due to my poor English writing skill, I think I will just share here for fun.
So the idea is that if the headmaster is too harsh punishing a tough girl (say Donna for example),
she will then attempt to flee like by swimming across the sea or climing through the mountains and forests.
After her failure to escape, the headmaster if at this moment still chooses to overdo his punishment, the girl will eventually
commit suicide, and thus a scandal will errupt to aware the public and lead to the bad ending...
This idea is intended for the education purpose of teaching people not cross the line...
First off, there are lots of people around here who would be more than happy to help proofread and edit your scripts. I don't have time for it personally, working on too many games as it is, but there are a lot of proofreaders here, and every game maker or writer of any kind needs one, even one who does that work. We all make mistakes.
As for the rest, owch, that is brutal. As it stands, I do not believe that we have a mechanic for 'going too far' other than with a couple specific examples, though I suppose each girl's punishment system is tailored to fit her, so something could be worked in.
On the other hand, I wouldn't mind seeing something similar in here for Donna or even Maxine, albeit maybe not to that extreme, just as part of the regular story line. Rather than us taking it 'too far' per say, they just don't take well to being punished in general. While it works well with Maxine, I like this better for Donna as seeing her getting in trouble because she can't do anything on her own seems funny. She tries to run away, maybe more than once, and each time she goes out, gets into trouble, and we come along as save her before taking her back to be punished after she recovers.
For example in the swimming one, she almost drowns, she could try to run through to woods and get attacked by an animal, try to dig a tunnel and cause a cave-in, and so on... Perhaps one of the other girls, like Rachel, and she tells us the plan, so we can be on the look out, that way we are there to save her when she gets in over her head. At first she is angry about having to be saved by him, but eventually she understands that we really only want what is best for her, and starts to follow orders, both due to her final resignation that she is not going to get away, and eventual gratitude to the HM for saving her over and over.