Actually that meter might pair well with a chastity belt for Callie from either her father or Derek.
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How about a "Horniness" meter so Callie has a reason to look at porn on her computer or do naughty things with Derek? Might go well with the "Guilt" meter you were thinking about... (Just the thought of her getting caught in the headmaster's office doing naughty things while looking at porn on her laptop...)
Well for one thing, that principal needs a cane for particularly hard cases like Callie. ;-)
Oh and that might result in a direct phone call from the principal instead of the automated one, or even worse: a visit to her house to speak to her parents in person. "I've paddled her 5 times this week alone." "We haven't been notified at all..." Hilarity ensues.
Well then, more suggestions since you're doing too well:
1) Purchase sexy outfits to tease Derek with. Parents will not approve...
2) On getting home from school, random bottom inspections. To not let you always get off scott free if you can hack the paddling notice...
3) I saw that I'd "learned to lie" but can't seem to actually do it in game. One word: mouthsoapings.
4) Collectable implements to bring to Derek for him to use on you, either voluntarily or not.
5) Date nights with Derek. You could probably just write 3 and have them randomized each Friday night. All should have some way to be nice or brat.
6) Grandma talks about her switch tree, but you never have to make that trek.
7) For when you're grounded, there needs to be a place you can put on medicine/ointment in private. A conniving teenager would not obey that rule... Perhaps at a friend's house, with or without assistance.
8) How can Callie's house not have a woodshed for these strappings and switchings? :-) Perhaps having to walk naked out there each time...
I hope some or all of these will be interesting for you. Simply an incredible job so far... Thank you!