>>43893557>>43893592I can tell you that Pokégirls were a thing for years. In Gen I, there was old school Misty hentai, mostly in relation to the anime. Same for Jessie and even Sabrina to a lesser degree. In the actual Game Freak office in Celadon City, one of the employees goes on about how cute Misty, Erika, and Sabrina are, though I can't remember if this was only in the Japanese games.
Hilda was designed by watching passing teenage girls and seeing their style in late 00's Japan. She and Hilbert were also given baseball caps to match N, and were specifically designed to appear somewhat cooler than what Sugimori tries to go for.