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I'm stuck on the Rachel punishment that opens up the dildo option. There is no mathematical combination to max out all 3 with 6 AP, and still have one leftover for the dildo insertion. I can certainly get within the range of that action maxing her out, but it won't let me choose it.

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I assure you it is possible. You can also just switch to easy mode under preferences and you have the option to be guided through the punishments.

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I found the walkthrough on your discord. Apparently doing it in the exact order listed allows you to select the final option. Getting to that point in other ways disallows it.

I noticed this as well. It's infuriating.