So I watched Udagawachou de Matteteyo and I really enjoyed it, especially that the guy sincerely enjoyed dressing up as a girl (he didn’t do it to get in somewhere or to trick people)

Does anyone know of any other films or series likethis where the male just enjoys cross dressing andisn’t trying to gain something from it?

Kuragehime. People tend to mistake him for a woman (and for the bulk of the drama/movie, FL's housemates think that he's a woman, a ruse that FL & ML keep to because don't want any man anywhere near their home), but he never presents himself as a woman.

https://mydramalist.com/26205-kuragehime (drama version)

https://mydramalist.com/9839-princess-jellyfish (movie version)