how do you get the jailor scene
After doing the first Adventure Guild quest, ignore John's rightful warning and let Charlotte get herself in trouble by drinking her worries away (though she does have sad circumstances that drove her to the point of being an alcoholic, she will get 15 days of jail for fucking things up really badly).
She'll end up in jail the following day, where you can either bail her out (500 gold iirc?), wait it out, or... what you would expect from any corrupt male guard...
If you keep her company, she will not end in jail and you will miss out on that scene, but you can always do that in another walkthrough or mess around with triggers if you want a "full green room". Being a pure lesbian Aura politely telling all men to fuck off unless they want to get fired, I pretty much had zero scenes unlocked on my 100% one.
Edit: Ninja'd by
Pretentious Goblin, heh.
Better instructions and much more straightforward so I recommend that post
I didn't do lewd things with Charlotte by the way! P-please don't misunderstand, I just wanted her Fire spells really badly so I just got a bit... heated up...