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Okay, well the ideas for Ash all involve him getting dressed as a girl and usually ending up with blonde hair, you know like the original 'Ashley', the reason why Is because that was definitely the most humiliating disguise/outfit Ash has ever worn in the series.
One of course is a Ash humiliation rp, the details we can discuss if you want.
Another would be an interesting one involving an OC from one of us doing a nuzlocke run, but the trainer wears diapers and has a hard time getting their Pokémon to respect him or her.
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"Power!! Glory!! Happiness! Culture, law, money! Food, the hearts of the people!! I have taken the first napkin!" - Funny Valentine, JoJo's Bizarre Adventure.