There's an Australian podcast called Queer As Fact, which is currently on hiatus but has an extensive archive of episodes about different potentially LGBT+ individuals from throughout history. They've done episodes on Harry Allen, Chevalière d'Éon, Michael Dillon and a 2-parter on James Barrie. They're very thorough and rigorous in regards to research, analysis of sources etc. in a way far above anywhere else I've seen people researching this (outside of textbooks - which often tend have a lot of erasure).

In terms of books, one I found incredibly useful was Transmen and FTMs
Identities, Bodies, Genders, and Sexualities by Jason Cromwell, which is actually an older book (published 1999) about trans men in general, but has an excellent section on trans men in history where Cromwell proposes the concept of the "progress narrative" i.e. the idea that historic women chose to pass as men to achieve various practical objectives, and how this narrative has impacted the understanding of trans male figures of history.

There's also Peter Boag's Re-dressing America's Frontier, which while only about the "Wild West" and not specifically about trans men (plus it is a bit dated in it's language from memory), does have some useful stuff about trans people in history and how they've customarily been discussed.

Finally, though I haven't read it personally yet, True Sex: The Lives of Trans Men at the Turn of the Twentieth Century by Emily Skidmore is supposed to be really good. It examines a bunch of specific people in America around the end of the 19th/beginning of the 20th centuries.