Scenarios that will end the walkthrough. You'd want to avoid them if you didn't save beforehand, or you play in Ironman mode. On this page Game Overs are sorted by tables according to the map where it's possible to earliest obtain them. If it's marked with *, you will complete achievements by getting those Endings.
Ask for staying in the Silajam inn either having not enough money, or lying about it (requires low purity/catamete perk + Charisma 3). Repeat three times in total. Fourth time you shall ask it's Game Over.
Force to deepthoat Daisy or Rose, twice. In the morning go to Town Square. Either wear Ring Gag there, or fail a check. When the option to pretend reshackling yourself comes, choose another.
Seat of Power *
Ask the Brothel Madame about odd jobs. When you giggle, say it's because her chair is creeking, than call her fat.
Finish the Brothel Madame questlines and do with her everything she ”likes doing for fun”. Then ask her for a marriage and choose whatever is needed.
Complete all quests for the Brothel Madame. Hire Lupa four times (it will cost 20 gold every time) and than agree to take responsibility.
Wearing no chastity, choose to give it to Mermaid, then get egged. Give birth, and with low purity/catamete perk marry her.