I was relistening to Feet of Clay by Terry Pratchett for emotional support reasons, and holy shit the transitioning subplot of Cheery is something else.
The main theme of the book is personal and body autonomy, but it's explicitly about the Golems. So Pterry made it implicitly about transgenderism. The transgenderism is very explicit tho.
For what we know about dwarfs in the Diskworld, they are all male. Some can bear children, but it's not visible from the outside, as all dress in a similar way, that is very conservative, and have long beards. When they marry both parties have a dowry.
When she is introduced she uses he/him both from her perspective and from Vimes. She is unusual for a dwarf because she is an Alchemist and doesn't care about weapons, but still looks and acts as a regular dwarf. It's only when Angua ("that can see with her nose") meets her, that we discover that she wishes to be a female dwarf. Angua smelled that she was a girl, and knows that there are other dwarf girls in the watch, but is the only one. Cheery's transition is social, but the text never mention whether or not she could bear children. She is not secretly a cis girl embracing her femininity, she is a trans girl finding a place to be her true self.
Angua is of course very important in her progress. I'd say that she is a true ally, but Angua the vegetarian werewolf is a queer metaphor in itself. It is true that initially she approached Cheery just because she wanted a girl friend at work, because "cops can be of all genders as long as they act male". But we see here and in the following books that their friendship blooms in something quite pure and beautiful.
The first thing she does is introduce Cheery to a bar "that people don't discover but gravitate to" where "everybody can be themselves without hiding". Angua still hides her nature of werewolf from Cheery for fear of scaring her off.
Now Cheery as a supportive friend that knows that she is a girl, and that everyone is a little scared of and won't go against. She has a support system and is protected. This is Ank-Monkport not Überwald.
She starts small. First a pair of earrings. Then lipstick. Then high heels (attached to proper dwarf boots), then even a skirt. "When you've made up your mind to shout out who you are to the world, it's a relief to know that you can do it in a whisper."
She goes to Angua with a list of possible new names. She chooses one that is similar to her old one, but pronounced differently. She is still a dwarf after all. And for that same reason, she keeps her beard.
The other dwarfs at the watch don't take well to this change, and threaten to ask Carrot to do something about it. But it's too late. Carrot himself, a dwarf by adoption, didn't react well when he saw her and heard Angua referring to her as a girl. But Angua took Cheery's side and called him off on his bigotry. "We have extra pronouns here".
By the end of the book she is interested in the Watch as a female officer. Angua gives her some of her dresses, and Cheery asks if she can share them with other female dwarves. In later books, we will see the impact she had in the dwarf community. But for now we just see her transition from the sideline, quiet and yet important. Fitting perfectly with the theme of body autonomy and freedom. And of course, the sweet friendship between two (queer) women.
To finish in a lighter tone, the way Vimes takes it in is hilarious. He is too busy to pay attention to everything that is going on, so he basically gaslight himself into thinking that he always knew Cheery as a woman. He notices the little changes but doesn't have time to think about it. By the end of the book he she/hers her without being told so XD