When people undergo ‘gender reassignment’ - no - even if a ‘he’ simply decides that he wishes, henceforth, to be known as ‘she’, the possessive pronoun instantly seems to leap out and smack you in the face. Take this morning’s news about Chelsea Manning, formerly Bradley.
There were more “shes" uttered in the space of a few seconds than I’ve ever heard in an entire episode of the ‘Mr and Mrs’ gameshow. Not that I’ve ever watched one.
It’s as though they’re deliberately hitting you in the chops with a wet fish. Gratuitous possessive pronouns really grate.