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Oooh, all those ideas seem good. And I think it'd be rather fun to have a scene like the one you described! Could be cute to have a seen where Dawn is being treated like a child one moment, like drinking from a bottle, leading right into her having an intimate moment with Ash...the boy confused about his feelings towards this the entire time...
That works fine! So Ash would be in the world, interacting with the girls and experiences with most wearing diapers? That sounds fun. Just to make sure, are you interested in Ash being diapered as well as a sort of exception to only girls wearing them, or no? I'm fine with either option, I'm just asking what you would want.