You will only be able to upgrade her masochism to lv 3 (enjoy rough anal) after you've met Alvarez. This is phase 3 of her corruption, so there's a few events ahead of you.I'm stuck with Gloria at level 18. I can not understand what she needs for 19. All the events for this level seem to have passed, but I can’t upgrade masochism to level 3, and further progress does not go. The task says that I have to discipline her, but I can't do it
To discipline her, call her into your office and select 'Continue disciplining her' action. Make sure that all conditions regarding her buffs and desire to cum have been met.