~2500 BCE Culture The Gala priests of Inanna in Sumer are described in a gender non-binary fashion or in a fashion suggesting males taking on female aspects of dress and speech. In prayers to Inanna, one declared “To turn a man into a woman and a woman into a man are yours, Inanna.”
~1300 BCE Culture Tutankhamun and his close male relatives as depicted in artwork show signs of gynecomastia, indicative of an excess of estrogen.
~8th century BCE Culture the blind oracle Tiresias features in The Odyssey. This mythic figure began life as a man, was transformed into a woman upon disturbing two copulating snakes, and after several years, repeated the incident and transformed back to a man.
669 BCE to 631 BCE Culture Ashurbanipal, king of the Neo-Assyrian empire, is reputed in later Greek histories (under the name Sardanapalus) to have dressed, behaved, and socialized as a woman. However those stories are generally now considered apocryphal.
~600 BCE Culture Medical In Scythia (approximately where Urkraine is now), there was a hereditary class of transfeminine fortune tellers of the cult of Artimpasa (Persian: Arti) known as ἐναρής (Eng: enaree or enarei), (from Persian for “not masculine”), who were assigned male at birth but took on traditionally feminine social roles in addition to their religious roles. They are also said to have taken various herbal anti-androgens and possibly even premarin-like mare urine derived treatments with estrogens for a degree of physical feminization. Medcrave Online Article
According to Sophie Edwards, the sourcing for their use of mare urine as a feminizing substance is plausible but circumstantial, based in part on Ovid's writings 600 years later.
~400 BCE Culture The story of Joseph in Bereshit/Genesis has him famously given a beautiful coat, a ketonet passim, which in English speaking Christian contexts is often described as a coat of many colors, but elsewhere in the Tanakh, in the Nevi’im, in Samuel, the only other place the term appears in the Bible, it is a descriptor of a dress “typically given to young maidens” and is what David gives his daughter Tamar. In the modern era, some have interpreted this to mean Joseph wore “a princess dress”. In addition he appears to be the only male character described, like some of the women, as being “shapely and beautiful” suggesting that Joseph was to some degree gender transgressive. [Note: the story of Joseph is set in a time period ~1000 years prior to when modern scholarship places its composition.]
~200 BCE Culture Medical with a name resonant with their Sumerian predecessors, the galli/gallae priests of the Phrygian goddess, Cybelle, ritually castrated themselves on March 24th, wore women’s style clothing, kept their hair long, and wore jewelry.
~100 BCE Culture Catullus wrote his “Epic of Attis” describing such a castration and the Galli.
1st century BCE and 1st century CE Culture First in the Epithalamium of Achilles and Deidameia and later in the Acheliad of Statius, the legendary Greek hero Achilles is given a backstory of having hidden on Skyros in the court of Lycomedes, at the behest of Achilles’ mother Thetis, while in disguise as a woman.
~200 CE Culture Medical Later in the Roman era, in Syria, Atargatis, a similar goddess to the Phrygian Cybelle, had a priesthood who castrated themselves and afterwards wore women’s clothing and performed activities and duties traditionally associated with women.
200 CE Culture Elagabalus - Or Marcus Aurelius Antoninus, a young Roman emperor, who, assigned male at birth under the name Sextus Varius Avitus Bassianus, presented herself in female attire and makeup and put the call out for a physician who might transplant a uterus into her. (Pronouns uncertain as are much of the details surrounding her as many of the stories relating to her may have been intended as political smears and may have been fabricated).
~400 CE Culture The Catterick Gallus - appears to have been someone who lived and died in what is now North Yorkshire, England buried in a similar manner to the gallai of Cybelle and Attis. The particulars of their role are not agreed on.