Sorry it didn't help. Maybe yours is bugged and mine is fine?
possibly, i've looked up multiple walkthroughs and read as many comments about it as I could find and no matter how I do it its always short by 1 point and i've tried it probably 10 times by now and I did the soccer event and tried as many things outside of the punishment as possible to see if it affects anything and no luck
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"