Possible Historical Trans Women
Perhaps possible transgender women seem to be more sparse in history because many societies deem male-to-female presentation as far more scandalous and therefore dangerous. This page details any figures from the past who may have been trans women.
Elagabalus, or Marcus Aurelius Antoninus Augustus is a disgraced Roman emperor who began their reign at age 14, and was assassinated by 18. They are mostly known for sex scandals and "eccentric behavior." They were married as many as 5 times with many alleged male lovers they appointed positions in government. They also allegedly prostituted themselves. They were said to have dressed in feminine clothing, referred to themselves as "Empress," and offered payment to any doctor who would operate to give them female genitalia. The truthfulness of these things is uncertain, as some details could have been made to slander the young ruler.