okay ive been thinking about it a lot and i think it's time i actually wrote it down bc the pratchett fandom can be a little transphobic! i wont lie. anyway:
trans characters in the discworld
(minor spoilers for thud!, monstrous regiment, and literally anything with dwarves in it)
first and foremost, the obivous one. dwarves. in the discworld, dwarves are a one-gender race, though they don't have a single sex. this just means that female dwarves are expected to be men, behaving like men and living their entire lives out as men.
this means that any dwarves who don't conform to this are considered unusual and usually looked down upon. now, in the tv adaptation of the watch, the dwarf cheery littlebottom was cast as a nonbinary character. this caused a lot of uproar because cheery is a woman. that's a huge part of her character: the fact that she refuses to conform to the gender norms set by her people. like, i dunno, nonbinary people? trans people in general? the way that cheery presents herself, fully bearded yet unapologetically female, really resonates with me as a trans person.
(cheery is in front of the man in red)
while i didn't really like the adaptation, i personally saw nothing wrong with cheery's casting. female dwarves have always been sort of a trans allegory to me, and i definarly think they were at least a sort of commentary on gender itself.
now we move to monstrous regiment, which is arguably terry's queerest book. you'd have to hope that a book centred around the concept of a girl dressing as a boy to go to war would be a little queer, wouldn't you? polly, the main character, is not trans, however. it could be aruged that she's sapphic, but that's a whole different discussion.
no, the trans characters in this book are maladict and jackrum, and though there might be some argument as to the valididty of these claims, i can pretty confidently back them up.
starting with maladict, the vampire joined the military in a different country to escape the opressive, suffocating expectations of womanhood in his country. though as the book presses on and more and more of the characters are revealed to be women, maladict only really tells polly his sex at the very end, and in private. he sees that it's more than a safe place to be a woman and yet he doesn't reveal himself. why?
well, because he's not one. you cannot honestly tell me that a woman behaves in such a way when given the oportunity to exist as a woman on their own terms. maladict remains a man.
(a note i want to add here to validate this claim. in the book thud!, sally, a vampire, explains to angua that when vampires turn into mist or bats and then re-form into their own bodies, men keep their clothes and women lose them. when mal turns into mist and re-forms again, he still has his clothes. therefore: man)
which brings us to jackrum, who's transness is a little more pronounced. jackrum joined the military to follow his lover, william. he ended up being much more sucessful than william, being promoted and gaining a reputation. but even after william died and jackrum gave birth to their child (we love a seahorse dad), he stayed in the military. he had a family to raise now, and his boyfriend was dead. he had no reason to stay, right?
only the idea of womanhood is no longer appealing to him. so much so that when they're sneaking into the kneck keep, both him and mal opt to stay behind (for jackrum, he’d rather miss the action than be perceived as a woman, even in disguise. for mal it was more that he was in a coffee coma but even if he wasn’t, i’d like to think he would have stayed behind as well).
there's a really beautiful line in regards to jackrum after his discussion with polly about going back to his family:
"Polly paused when she got to the door. Jackrum had turned her chair to the fire, and had settled back. Around him, the kitchen worked."
this is the moment that jackrum realizes that he doesn't have to be a woman. he can go back to his family and be the father he's always wanted to be, he can keep his legacy and his glory and his pride. he knows that it's okay to be a man now, that he no longer has to be a woman in disguise. that sudden change in pronouns always gets me.
you can have any opinion you want, but personally, these stories really resonate with me as a trans person, intentional or not.