Not to deadname my boy, but he was originally born as Bellarose Baggins, named after his mother, Belladonna
His mother knew before he did. It wasn't any particular thing, it was a combination of little things and a mother's intuition
She used to hand-make his dresses, and while he wore them, Belladonna could see it in her child's eyes that he hated them
The day she caught him in their bedroom, wearing his father's clothes, she knew her gut was right, and she was okay with it
Bungo was a little more conservative at first, worried about what the other hobbits in town would say, but his wife pulled him into the other room and set him straight real quick
After his focus was shifted to his child's happiness, their reputation didn't seem quite as important
But it still was, so after that, Bungo started teaching him how to be a respectable man instead of a lady, and Belladonna started making him trousers and vests to wear
For a few months, while names were still being considered, he simply answered to 'Baggins,' when out in public
But one day he approached his father and asked that had he been born male, what he had wanted to name him, and Bungo was actually rather excited to finally use the name 'Bilbo.'
So it was decided from then on, he would be known as Bilbo Baggins
Being trans wasn't some huge taboo thing in the Shire, but people like to gossip and be a little too nosey, which is why Bilbo never really made it a huge deal and his father expertly shut down other's questions before his son could either be made uncomfortable or before unnecessary rumors were started
Lobeilia and Otho aren't intentionally transphobic but they are ignorant and, again, nosey
Lobeilia is the type to ask intrusive questions like, "So are you going to get the surgery?" And Bilbo redirects the conversation effortlessly, having learned how to navigate uncomfortable conversations from his father
Due to trans people not being seen as horrible or taboo, hrt is normal and easily accessible, made up from various herbs and easily made into a tea
HRTea
Hormone Replacement Tea
I'm a genius
When Gandalf comes back around to meet with Bilbo, he almost worries he's either got the wrong house or that the Baggins family moved out for some reason, but when he smells the tea that Bilbo is drinking, he quickly understands and moves on
"To think I've been Good Morning'ed by Belladonna Took's son, as if I were selling buttons at the door!"
"I beg your pardon?"
"And my pardon you have, Mr..."
"Bilbo."
"Well you've changed, and not entirely for the better, Bilbo Baggins."
When the dwarves arrive and start eating all his food, Kíli finds his tea and scrunches his nose up at the smell, asking why it smells like medicine
Bilbo quickly takes the jar from his hands and explains that it is medicine, and it's the one thing he'll have to firmly put his foot down on
Óin takes the jar from his hands and gives it a sniff, immediately recognizing what it is and what it's for, simply handing it back like "Ah, good for you laddie, always nice to meet a self made man!"
This leaves Bilbo in an odd mix of still feeling stressed that his house is being ransacked, but pleased that it's being ransacked by such supportive individuals
When he's packing his bags to chase the dwarves down for the adventure, he packs like three full jars of his tea
Literally no one likes the smell of it, but everyone's been made aware of what it is so no one really fusses about it
With how often they're traveling, running, and getting into battles, Óin makes him stop binding his chest so it doesn't warp his ribs or harm his lungs
Óin: You're going to have to stop wearin' that if you want to be able to outrun that dragon when we finally get there, lad
Bilbo: O-Oh, but-
Bofur: Don' worry, Bilbo! Bombur's chest is bigger than yours :D
Bombur: Proud of it, too!
Needless to say the dwarves actually make him much less self conscious about his chest
After months of traveling together, he actually feels comfortable being shirtless around them when swimming or bathing, especially since none of them mention it or even pay his chest any mind. They're all more focused on harassing each other than to look at his chest
It's actually during one of their stops to swim and bathe that he notices Kíli has scars on his chest, under his pecs, and questions him about it
"Oh yeah, I'm like you, Mr. Boggins :] that's why my beard doesn't grow in very well."
This is when Bilbo learns that being trans is so normal in Dwarf culture that they don't even really blink at it
It's also how he learns the Khuzdul words for it
Khulnâla for transmasc, directly translating to "man path"
Khuninâla for transfem, translating to "woman path"
He asked if there was a word for people who didn't identify either way, and Balin was the one to tell him it was tadmênu, meaning 'third soul'
Bilbo does eventually get top surgery. After Erebor is reclaimed, he travels to Rivendell to see their finest healers
He does not, however, get bottom surgery, since I'm projecting myself here and saying that his lower parts don't make him super dysphoric
He's happy with just a flat chest and goes back to Erebor to show it off to his friends, who are all very supportive about it
My headcanon is that trans people in Middle Earth are common it's just that hobbits don't talk about it ever. Because hobbits don't really talk about anything out of their "norm". Everyone else is just like "yeah she got her husband pregnant recently. Third child; very virile wife."
A scenario;
Bilbo: I don't feel well. I think I'll skip sword training today.
Thorin: Are you hurt? You're clutching your belly. Should Oin check for wounds?
Bilbo: No! No, I'm fine. Just- Just a stomach ache.
Thorin: Then what's with the blood-stained cloth?
Bilbo, shoving his laundry in his pocket: Nothing-
Thorin: ???? *realizes* Oh- Your moon cycle. Of course, you don't have to train this week. You should be resting.
Bilbo: ??? You??? Aren't weirded out or???
Thorin: Of course not. Do you need anything?
Bilbo: *completely at a loss but undeniably happy*
thinking about thorin eating out bilbo, bilbo threading his fingers into thorin’s hair and tugging a bit, grinding against his face, and just rubbing against the friction of his beard while thorin grips his thighs
Hobbits are peculiar and queer little creatures. In just about every sense of the word. They are strange, with their short statures, round bellies, hairy feet, and pointed ears. But they are also just very gay. Such is the nature of one that lives in communal living where foods and ale are rich and aplenty and safety is just the order of the day.