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Alright well the bet thing sounds pretty good. But before the bet we can have Trixie, assuming Twilight is going to lose, put a certain spell on the diapers that makes the wearer actually use them anytime they have to go. So with the bet, it could come up as a draw so they both have to wear diapers for a week. Also im fine with you as Twilight, it would give me a chance to play as Trixie (my favorite character)
Would it be alright if Derpy invited Fluttershy along and I play Fluttershy? We can both be diapered characters that way. And we can make it as we go along.