It is possible. I have Rachel @ Level 10. If u read the "Headmasters Pet part 2" it tells u what u need to do next (mostly teach football and then have fun in the showers with Miss Newman too) During punishment, some of the positions give u Humilation points, so do those first, then do photos & maybe body search (cant remember sorry) Then work backwards to know how many points are remaining. ie if u need to put the dildo in Rachels arse, see what points it gives you, then work out how many pain and pleasure points u need. And dont forget to change to Headmaster so u can Straddle Rachel. Good luck
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