Here is the full list of all 7 Trapped with Jester achievements. It takes around 0-1 hour to unlock all of the achievements on Windows.
Smack Jester.
Obtain Ending 4: You’re Boring
Obtain Ending 3B: An Unwilling Pet
Obtain Ending 2: A Blasphemous Partnership
Obtain Ending 1B: My Master
Obtain Ending 1: Our Vow- Until Death Do Us Part
Obtain Ending 3: An Obedient Pet