Do you need to increase each bar to 3 or 4? For 3, do the best you can (you won't max it) then spy on her room. You'll see her friends use lotion on her bottom (if I'm remembering correctly). You can then buy this and use it in punishments. This will be the key to levelling Rachel (and Cassandra) up.
If you've done that, then make sure you've maxed Debbie too. This should give you the options you need to level up further.
I think he's talking about the same thing I'm having trouble with. In headmaster's pet pt 2, you have to get her pain, humilation and pleasure all to 9 and still have an action point left over when starting with only 6 action points. I just can't figure out the correct actions to take to reach 9 on all of them. At least not yet after trying various combinations over the past hour. Sorry, you actually have to get humiliation to 16, not 9 like the pain and pleasure.
