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Personally, I wouldn't be heavy-handed with it. Quite the opposite. The player seems to be giving you the opportunity, but test with smaller things first. Are women treated differently to men in the campaign? Women's work/man's work, expected to be silent when the real men are talking? If so, it would be enough to use that against him occasionally. If he doesn't like it, stop. If he seems to be enjoying playing out the challenges, keep it up. As a GM I would usually ask the player if plot like this is what they want before stepping in. "Your character is now a man in a woman's body. Do you want me to play with that in future? Or ignore it?" Also watch the other players' reactions the first time you bring it up. If they're uncomfortable, also stop. Do not dive in straight away. Edge up to it.
Reflecting the character's previous treatment of women bck on him might also work. Especially if he's been a rake or white kight or other negative male stereotype when it comes to interacting with women.
But do not go big on this until you're suer the player and the group are on board.
EDIT: To be clear, I'm a cis-het, male gamer in a primarily cis-het male group, so advice may not be appropriate. We've had female chracters for male players before but it's never made a big deal of and one player even forgot our cleric was female becuase the player was male, which caused some amusement amongst players or a couple weeks.