François Timoléon was dressed by his mother as a girl from birth. There is a memoir you could read, but it's in French.
https://archive.org/details/memoiresdelabb00choi Quote from
this article: "The early seventeenth century was a time of both political and social chaos in Europe. In 1602 "the French parliament condemned an hermaphrodite to death because he made use of the sex which he had abjured", wrote Eugene de Savitsch "Hermaphrodites were forbidden to be judges, advocates and university rectors." Fortunately, by mid century such attitudes had softened a great deal, and many even had reversed in France. Otherwise, the likes of Francois Timoleon de Choisy (1644 - 1724) would never have been able to 'come-out' as he did. Better known as the Abbe de Choisy, due to his appointment to the abbacy of St. Seine, he was a member of a very influential family at court, and because of this he may have gotten away with much more than others of lesser station in society. Choisy's life has been well documented by others, as well as his own very detailed memoirs. By all accounts he was the classic transvestite, never attempting to disguise his biological sex, but frequently going about in public in full female attire and expressing a deep regret for not been born a girl. Choisy's mother dressed him as a girl until he reached eighteen when he began appearing in public as a man. At least one historian has suggested a political motive behind his cross-dressing: he was deliberately feminised so as never to present a threat to King Louis XIVs throne. Be that as it may, Choisy never seems to have had any political ambitions and seems to have been quite contented with his public outings at the opera, the theatre, balls and other events dressed in the most lavish of female fashions.
Choisy was often visited by young women in his chambers. His fascination with female accoutrements made him something of an expert on women's fashions and prominent society matrons brought their daughters to Choisy for advice. According to his own memoirs he took these young maids to bed before their mother's eyes, but did no more than fondle and kiss them. He did, however, manage to get one woman pregnant, a well known actress called Roselie, whom Choisy enjoyed dressing up as a man, and the pair of them strolling about the streets of Paris with she as the husband and he as her wife. As Choisy aged he continued to dress as a woman less and less and spent his final years reminiscing on his youth when he was admired by fashionable society as the prettiest girl in town."
King Henry III cross-dressed, but I don't think there was a major reason. Edward Hyde was accused of cross-dressing also.
