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Trans Torah
(כו) וַיֹּ֣אמֶר אֱלֹהִ֔ים נַֽעֲשֶׂ֥ה אָדָ֛ם בְּצַלְמֵ֖נוּ כִּדְמוּתֵ֑נוּ וְיִרְדּוּ֩ בִדְגַ֨ת הַיָּ֜ם וּבְע֣וֹף הַשָּׁמַ֗יִם וּבַבְּהֵמָה֙ וּבְכָל־הָאָ֔רֶץ וּבְכָל־הָרֶ֖מֶשׂ הָֽרֹמֵ֥שׂ עַל־הָאָֽרֶץ׃ (כז) וַיִּבְרָ֨א אֱלֹהִ֤ים ׀ אֶת־הָֽאָדָם֙ בְּצַלְמ֔וֹ בְּצֶ֥לֶם אֱלֹהִ֖ים בָּרָ֣א אֹת֑וֹ זָכָ֥ר וּנְקֵבָ֖ה בָּרָ֥א אֹתָֽם׃

(26) And G-d said: ‘Let us make man in our image, after our likeness; and let them have dominion over the fish of the sea, and over the fowl of the air, and over the cattle, and over all the earth, and over every creeping thing that creepeth upon the earth.’ (27) And G-d created man in His own image, in the image of G-d created He him; male and female created He them.

Breishit Rabbah 8:1
"And G-d said: let us make man, etc. . . . R. Jeremiah b Leazar said: When the Holy One, blessed be He, created Adam, He created him an hermaphrodite, for it is said, Male and female created He them and called their name Adam (Gen. 5:2). R. Samuel b. Nahman said: When the L-rd created Adam He created him double-faced, then He split him and made him of two backs, one back on this side and one back on the other side."
"The midrash, classical Jewish exegesis, adds that the [first human] being formed in G-d's likeness, was an androgynous, an inter-sexed, person . . . Hence, our tradition teaches that all bodies and genders are created in G-d's image, whether we identify as men, women, inter-sex, or something else." - Rabbi Elliot Kukla, "Reform Devises Sex-Change Blessings", 2007.
(ה) לֹא־יִהְיֶ֤ה כְלִי־גֶ֙בֶר֙ עַל־אִשָּׁ֔ה וְלֹא־יִלְבַּ֥שׁ גֶּ֖בֶר שִׂמְלַ֣ת אִשָּׁ֑ה כִּ֧י תוֹעֲבַ֛ת ה' אֱלֹהֶ֖יךָ כָּל־עֹ֥שֵׂה אֵֽלֶּה׃ (פ)

(5) A woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman’s garment; for whosoever doeth these things is an abomination unto the L-RD thy G-d.

Babylonian Talmud, Nazir 59a
"What does the Torah mean by this verse? You might think that it simply means that a man may not wear a woman's garment and a woman may not wear a man's garment. But behold, it has already been said [by previous commentators in reference to this verse] that it is completely off-limits! But there is no to'evah ("abomination") here [it is not a completely off-limits behavior]! [Therefore], the verse must mean a man may not wear women's clothes in order to sit amongst women, and a woman must not wear men's clothes and sit amongst men."
Mishnah Bikkurim 4:1-2
An androgynos is in some respects legally equivalent to men, and in some respects legally equivalent to women, in some respects legally equivalent to men and women, and in some respects legally equivalent to neither men nor women.
  • "The rabbis of the Mishnah identify at least for possible genders/sexes: the zakhar (male) and the nekevah (female), as well as two sexes which are beyond male and female: the tumtum and the androgynos. The Talmud sees the tumtum as a person whose genitals are obscured, making it difficult to discern whether he/she should be classified as male or female. The androgynos is a person who has both male and female sex traits." - Rabbi Elliot Kukla, The Passionate Torah: Sex and Judaism, 2009, p. 193.
  • "The writers of this text appear to have performed the postmodern task of managing perceptions about dual-sex being, so that the community might recognize the truth of a complicated sex, rather than make a mistake and misinterpret a being who looks and behaves in public like a man." - Noach Dzmura, Balancing on the Mechitza, 2010, p. 165.
Shulchan Aruch, Orach Chayyim 696:8
"It is permitted [for a man] to dress as a woman on Purim."
  • ". . . so too the practice of dressing up in masks on Purim, a man wearing the attire of a woman, and a woman wearing the accessories of a man -- there is no prohibition of this, since what they are intending is merely joy . . . " - Rabbi Moses Isserles, 1520-1572.

(א) אנדרוגינוס יש בו דרכים שוה לאנשים ויש בו דרכים שוה לנשים ויש בו דרכים שוה לאנשים ונשים ויש בו דרכים אינו שוה לא לאנשים ולא לנשים:

(1) An Androginus (a hermaphrodite, who has both male and female reproductive organs) is similar to men in some ways and to women in other ways, in some ways to both and in some ways to neither.

(ב) כיצד שוה לאנשים מטמא בלובן כאנשים וזוקק ליבום כאנשים ומתעטף ומסתפר כאנשים ונושא אבל לא נישא כאנשים וחייב בכל מצות האמורות בתורה כאנשים:

(2) In what ways is s/he similar to men? Like a man, s/he is considered unclean through semen; is required to perform yibum (to marry the widow of a childless brother) like a man; dresses and cuts hair like a man; marries others and is not married off, like a man; and is obliged to perform all the commandments in the Torah, like a man.

(ג) כיצד שוה לנשים מטמא באודם כנשים ואינו מתייחד עם האנשים כנשים ואינו עובר על בל תקיף ולא על בל תשחית ולא על בל תטמא למתים כנשים ופסול מן העדות כנשים ואינו נבעל בעבירה כנשים ונפסל מן הכהונה כנשים:

In what ways is s/he similar to women? Like a woman, s/he is considered unclean through menstrual flow; s/he must not be alone in the company of men; and does not share [the inheritance] with sons; and cannot eat most of the holy sacrifices, like a woman...

Tzitz Eliezer: Orthodox Responsa from Rabbi Eliezer Waldenberg (1919-2006)
In his large collection of responsa on Jewish law called Tzitz Eliezer, Rabbi Waldenberg (who served on Israel's supreme rabbinical courts) addressed some specifics regarding transgender people and halachah, the last of which is considered a particularly important and controversial statement.
I also saw in a book called Yosef Et Achiv (by Rav Yossi Plaggi, z”l), (3:5) that asks… if there’s a case of a woman who led a normal life for years and then became a man, does he need a get [divorce document] because when he got married she was a woman, or is there no get because he isn’t a woman? … It seems to me in this question that there is no need for a get because he’s a man and not a woman.
***
And as I said, as for a man like this—who was a woman who changed to a man—when he says morning blessings, he does not say, “who did not make me a woman,” because although he came out of his mother’s womb and into the world as a woman, he should say, “Blessed are You, Lord our G-d, Ruler of the Universe, who has changed me into a man.”
***
The identity and birthright of a human is not expressed by the separate organ parts of his body—and this will be the most important—but by the spirit and the soul which are within them. The Chatam Sofer got it right when he wrote that the body is not the human; rather the body is a bag made of dust and within that bag is inner wisdom, knowledge, and thoughts, which are the true definitions of personality.
The Rights of Transgender and Gender Non-Conforming Individuals (March 2015)
The CCAR made a resolution to affirm the full equality, inclusion and acceptance of people of all gender identities and gender expressions; affirm the rights of transgender and gender non-conforming individuals to be referred to by the name, gender, and pronoun of preference in our congregations, camps, and schools regardless of physical presentation; encourage Reform congregations, congregants, clergy, camps, institutions, and affiliates, including NFTY, to begin or continue to advocate for the rights of people of all gender identities and gender expressions; work in collaboration with other Reform entities to create ritual, programmatic, and educational materials that will empower Reform institutions to be more inclusive and welcoming of people of all gender identities and expressions.