How about if we have where when Ash goes off to Unova instead of traveling with Iris and Cilan Jessie either finds out about his bedwetting and/or kidnaps him, then forces him to journey through the region while acting as her baby?

I kinda like the second one more. The part about there being a rule seems a bit unnecessary though. It could just be he's embarrassed and she's blackmailing him. Alternatively, she could just kidnap him and make him be her baby.

Naruto:

Naruto one day is in the leaf village hospital due to training exhaustion and a few injuries he wakes up and loos around as he's confuses as he didn't know he was in the special needs part of the hospital

Anyways Naruto see's a pack of adult diapers that was next to his bed buddy and he being curious takes one and puts it on

Once he is done Tsunade walks in and Naruto tries to hide it out of embarrassment but Tsunade being a professional medical kunochi knows instantly but and let’s it slide

However she starts to treat him like a baby little by little in the process

Pokemon :

Jessie always wanted a child but being in team rocket she never got to settle down but all that changes when she see's ash Ketchum buying pull-ups

That's right ash Ketchum is still a bed wetter even though he's officially a pokemon trainer

Anyways jessie seeing this realizes that she can make her dream come true by making a deal with him as it can be forbidden for kids who still act like baby's to be pokemon trainers

Oh you mean do the rps in a more modern setting than the show is usually depicted, yeah sure I'm fine with that.

I'd be down for either Pokemon or Naruto. Do you have any scenarios in mind?

My three choices are

Pokemon
Naruto
One piece

(If we do Naruto or one piece I would like to do modern times of that's ok)

Yeah. .

Uh I don't really understand the question. Like you mean current world events?

Question how do you about the modern times

Naruto, one piece, Cardfight vanguard, dbz, delicious in dungeon, pokemon, avatar (anime-esque) there are others, but these are the first that come to mind in terms of stuff I'd want to rp in.

Can you tell me them please. ?