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Can we get into a romantic relationship with someone eventually (besides Ned cause I'm not into him and he's also too unhinged) ? Also it'll be impossible to have good grades if I never give the Headmaster any sexual favors ?

There are already some options to come at least close with Ron, and I intend to develop this further. And I would like to add something with Vincent at some point, so I hope to add a bit more romantic soon. 

Since the headmaster controls the grades, it is pretty tight with his opinion of you. You can increase them with Ned for a bit, and I plan to have other means to increase them in the future, but for now, it depends pretty much on the headmaster's favor.

Alright, thanks. Granted I have a last question about the wrestling match (where I'm at currently), if I somehow manage to lose it will someone else be publicly exposed naked and tied up in the gym ?

You are being tied up either way. If you win you can choose not to wear the chastity cage though.