Just Like a Woman (1992)

Gerald is a smart, young, high-flying American banker. Everything is great until his wife finds another woman's underwear in their bedroom and subsequently throws him out. He finds lodgings with Monica, a recently divorced 50-year old housewife, who is smitten with Gerald. But after their first night of love, Gerald avoids her. Monica feels used and betrayed until Gerald confesses he likes to dress up as a woman. Monica learns to accept and eventually support Geraldine, Gerald's alter ego. Based on the novel by Monica Jay.

Unfortunately the movie Just Like a Woman is not yet available on HBO Max.