Our stories are extremely different, and she is no longer Orthodox. But she pointed me to
Chassidic, kabbalistic, and Talmudic sources that completely blew my mind: a teaching from the 18th century Chassidic master Rabbi Yechiel Michael of Zloczow that Isaac Avinu was born with a male body and a female soul; medieval kabbalistic sources about a man reincarnating in the body of a woman and about the need for all human beings to be simultaneously male and female; a midrash in the Talmud about Dinah bas Leah’s sex being changed from male to female while she was still in the womb; and more. These sources blew my mind, because I had thought that no pre-feminist Jewish writings had anything to say about trans people, let alone affirming the complexity and mutability of Biblical figures’ sex and gender! And yet, there it is, loud and clear, in an 18th century Chassidic text: “It is known, according to the
sod [mysticism] of reincarnation, that at times a female would be in a male body, because for reasons of
gilgul [the cycling of souls], the soul of a female would come to be in a male.”
Alright, let's break this down. Aside from the fact that no actual Chassid would pay any attention to someone unironically using the phrase "Chassidic master", this is masking two important points. Firstly, all of the sources cited, being pre-modern religious thinkers who were conservative even by the standards of their eras, would have viewed troons as abominable homosexual perverts worthy of stoning. Hell, the Talmud concludes that a man is (technically) liable for the death penalty if he penetrates himself (yes, this is an actual passage). Do you really think they'd embrace troonism?
Secondly, and to go to the heart of the matter, this is ignoring the motivation for all of those statements. Most pre-modern Jewish thinkers, as well as most pre-moderns in general, considered women as inferior, flawed versions of men. A man would be reincarnated in the body of a woman as punishment for sins committed in a previous life. Even Abby Stein has to admit this on the source sheet Shuli links to:
Sometimes a man may reincarnate into the body of a woman because of a sin, (cultural context) or something similar. This woman who has received the soul of a man will not be able to conceive and become pregnant.
Oh, what's that (cultural context), you ask? Well, the original Hebrew text, censored by Stein, reads "because of a sin such as homosexual intercourse". But this writer would totally support troonism you guys!
Likewise, Dinah's sex was changed to female because a male child would have resulted in her mother Leah having a greater share in the ancestry of Jacob's children that actually counted - his sons. Not to be too woke, but these sources aren't affirmations of trannies - they're affirmations of sexism and misogyny. On the other hands, MtFs are all about that, so who knows.