Today is Bloomsday, named after the character Leopold Bloom in Joyce's Ulysses, and the day in 1904 when James Joyce first walked out with Nora Barnacle.

Published 100 years ago in Paris, James Joyce's Ulysses is a book replete with references to cross-dressing men and women, and has, I think, the first description in a novel written in English, of a woman (Molly Bloom) swallowing semen. Earlier in the day, her husband, Leopold has masturbated while ogling the disabled Gerty MacDowall who is sitting in a provocative manner on Sandymount Strand, totally aware that an older man is pleasuring himself as she does.

Joyce himself was known as something of a dandy, and scholars have spent many hours and much print on Ulysses and sexuality, with I think, a general view that Joyce was generous in his appreciation of the possibilities of sexual pleasure, something WB Yeats was keen on but in private being too much of a snob to discuss it in public, albeit at a time when such things were not considered 'decent' and when Ulysses was declared 'Obscene'.

Ulysses may also have the first reference to Cunt in English language since its previous appearances in Shakespeare's Hamlet, and Chaucer's The Canterbury Tales, but I am not sure of that. ('The grey sunken cunt of the world').

As there are too many references to it, but one in particular, in the 'Nighttown' episode, I have some
links below where you can find Bloom dressing as a woman while Bella Cohen dresses as a man and humiliates Leopold, the Everyman of Joyce's daytime perambulations through Dublin and the World.

Cross-Dressing in Ulysses
Cross-dressing in James Joyce’s Ulysses | Clare Flourish (wordpress.com)

Blurring the Lines: The Ambiguity of Gender and Sexuality in Ulysses (trinity.edu)

POJ-6.pdf (us.es)

The Red Light District of old Dublin
Monto - Wikipedia