This is where I can't. I can't get her pleasure bar to full, thus she can't level up. How?
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.