I have some problems with two quests. The first one is Reluctant Rebel. The quest requires punishing Priti. But there is no way to maximum the pleasure bar to get Priti to level up. The second quest is the Maid for Punishment, which requires finding Harriet to perform a body search. And I couldn't find her even know I had done all the requirements like find her on Monday and Friday evenings at the sport centre lockers.
Depends on which level you are stuck on. Hard to tell from your description, but assuming it is from L2 to L3. For that, you need to have bought the paddle and the ointment. You also need the action 'massage inner thigh' which you get when advancing both Ms Newman and Debbie's questline; if Pleasure is the issue, it sounds like this is the action you are missing.