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Chapter 1 - Don't take knife and try saving the princess, when the narrator drops the blade near you, slay the princess until you get an option to give up, this gets you to the beast
Chapter 2 (The Beast) - go in without a knife, move out of the way of the first attack, then keep asking questions and dodging out of the way, you'll eventually get killed when half your body is eaten
Chapter 3 (The Den) - if you did things right, you should have the Skeptic as a voice, from here, try to lure the princess out of the shadows, you'll be able to escape successfully and get the achievement
For Past the Point of No Return
Finish a route of your choice, doesn't matter what.
For the 2nd route, try to get the good ending. The mound won't be happy and won't let you.
You need to interrupt the 'Good Ending' for this achieve. So, on your second or third vessel slay the Chapter 1 Princess without asking any questions, and then just agree to wait forever.