I was seriously embarrassed for her myself as it started to come into focus who she was to be paired with

Not knowing what is to come is such a powerful feeling when the story really sets up a deliciously horrible set of possibilities
I don't envy the task you set before yourself of rising to that occasion and writing the rest of this
2 suggestions if you'd like:
1. Set up the next chapter to give some breathing room to the main storyline by doing the assembly with Miss Monroe next. Perhaps maybe after the professor spanks her have a surprise for her and get some volunteers from the audience
2. As a side event that chapter have Jason talking to other boys in front of our heroine Kimberly have them asking him questions about owning her, eventually turning to questions about borrowing and leading to the discovery that because all the other girls have partners that care about them, they are shooting down even requests to watch some of the punishments. (I was thinking side event because maybe not actually do anything to Kimberly except make her hear it and try to protest) or maybe make it a chapter and have Jason let the other boys grope her a little or something small.
3 bonus thoughts have the Doc peace out claiming a prior engagement (but really it turns out to be an act, she doesn't believe, and it's for the money. If she has to strip once in a small group to sell it, so be it
Thanks so far. This is quite the imagination fuel already