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It will add itself to the list to buy once all other criteria is met. check your task list for Amy (spanking connoisseur). you may need to advance Debbie's story first.

(2 edits)

I cannot advance Debbie's story cause for that i need to advance the main quest "Many Hands For Many Bottoms" and for that i need to advance Amy's quest " The Spanking connoisseur"  and "Teaching Miss Potts"(for this i also need Amy). I'm on 9 step for Amy's quest and it says: "Catch Amy misbehaving and sentence her to private punishment", i cannot cath like for more than 50+ days, all i can is to see her at class without her tie and then punich for that but i cannot lvl up her here, i read the hint at right top corner and it says: pass the rule allowing you to punish her yourself(i can do this) and purchase the chastity underwear from the online store(that i don't have there). Then wait for her to be late for class again( i quess she's not gonna be late till i buy that underwear).

nvm, i fixed it by puniching amy when it was not written lvl up and it did lvl her up...