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Hmm... that depends on how far is too far for you, but I would still like to include bathroom denial, bondage, and desperation (especially bathroom denial and desperation, but I can do without the bondage).
As for who would blackmail Cheerilee, one possibility is one of her students. Diamond Tiara would be the most in-character, but we can also do one of the Cutie Mark Crusaders since we know them the best. But I would highly prefer that it's an adult character. Are there any characters you are thinking of?
So, the elevator pitch of the idea is basically that a rich woman adopts her ex-boyfriend who she broke up with due to his self-destructive work ethic to try and fix/comfort him as a baby-slave by preventing him from doing any kind of work at all to stop his self destructive stress-spiraling
This creates conflict because not being able to do anything while she does everything for him makes him feel even worse.
It's a sort of setting/general concept I like because I feel like it's both grounded in the present day while opening up opportunities to go completely ham with the baby stuff
Plus, my idea involves quite a bit of bondage, since I remember you're into that
