One big example in anime for this is Gintama, where an ex-samurai lost his wife early on leaving him as a single parent thanks to that his son was always a sad, lonely troublemaker, to combat this, the father started wearing female clothes to pretend to be a mother that his son needed/wanted.
In usual Gintama fashion, they played it up as funny, creepy and gross but in the end his son started accepting him for who he "is".
Oh, he also opened a bar of degens like him for degens that want to be flirted with by men in drag
Honestly my most hated storyline, still my 10/10 anime.