This is an excellent article on teaching transgender using a historical framework by Elizabeth Reis, Emeritus professor at University of Oregon. Published in 2004, the article functions simultaneously as a personal exploration of pedagogical experiences and an invitation to a practical dialogue about what literature to offer students.
Her pedagogical choices are valuable points of departure, such as insistence to students that transphobia will not be tolerated or her forcing students to think about how questions within the transgender field upend our assumptions about the hard lines drawn that determine biological sex.
Reis also engages with current and age-old historical debates, such as how to avoid the issue of presentism when searching for a way to describe "transgenderism" before the term "transgender" became part of popular discourse. Using the term berdache coined by French colonists to describe Native Americans (mostly men) "who lived, dressed, and worked as the opposite sex," (169) she demonstrates how the problematic use of terms such as berdache and two-spirit people tend to distort, rather than clarify. She concludes that far more useful, however difficult, would be to use names Native Americans "themselves employed." (170)
To further support this line of reasoning, Reis echoes frameworks such as D'Emilio and Freedman's Intimate Matters (1988, 2012), noting how "women who dressed as men" were initially and simply assumed to have interest only in carnal relations with other women (170).
Reis touches on complications with other terms such as intersex and transexuality: the former a result of activists shrugging off the mantle of a pathologized body and critiquing the practices of medical professionals who made decisions for people with so-called "ambiguous anatomy." (171) In so doing she critiques the DSM's GID (Gender Identity Disorder)* This has largely been replaced with "Gender Dysphoria," but is still coded as a disorder in some sense. She questions the privilege of transexuality--who can afford to alter their bodies? And without a diagnosis, one is often denied services.
After revealing several of the questions facing scholars and activists in her course, Reis offers her syllabus with reading list, and it begins strongly organized by chronology and later rests more heavily in theme, though often they are more contemporary themes.