I really wish the prison scene is finished.... though I wanted to help... unfortunately I don't have the best writing ethics '''OTL btw, is Obedience capped at 50? I tried to raise it but its stuck there even with 0 self esteem and willpower
Have you been submissive to Elly each time she visits you? Doing this raises your "Mistress Elly's Training" rank every once in a while, so I recommend doing this if you want to get past 50. other than that, choose "Self Pity" and "Discipline" when you decide to study in your cell.