2 years later and it is still bugged. Get to the last step and it allows it then stops saying "This needs to be the final action of the punishment" and it will not proceed to level 10. I have looped back on this same thing 30 times now. No change.
Order to strip naked. Position with hands above head. Take her picture. Position bent over the desk, give her a paddle and ruler spank (or ruler and paddle-no difference). Put in diaper position, insert dildo. Put over knee, choose anal dildo. Choose to make her straddle Headmaster' lap. Choose to have sex with her... "This needs to be the final action of the punishment"