>>125510615Infiltration, like a rookie cop infiltrating an all female gang or a spy disguising himself as a woman to stay concealed and inconspicuous, that happened in a Batman comic where Bruce dressed Tim up as a female doctor to infiltrate a hospital since he was too short and young looking to be a convincing male doctor.
A curse, like some powerful bandit or warlord is transformed into a cute weakling by some God, Witch or Fairy, and having to deal with having to use brains and cunning over brute force.
Or a grave robber/thief stealing some artifact said to give the user eternal youth, the power to control others or something vague like that, and it ends up turning them into a femboy.
Fashion, a character could just like being a femboy for aesthetics, if we're going with more reluctant or forced stuff it could be a job for product testing or modeling and he didn't read the fine print about what exactly he'd be wearing or testing.
It could just be the culture, some lost tribe or obscure province values the femboy look as what's truly masculine or commonly attractive for their culture