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Lola by The Kinks is about a young guy losing his virginity to a black trans woman. Don’t know if that counts.
I love the song, especially the cover by Ripe, but I don’t remember a mention of Lola being black? I know she had a “dark brown voice” at least
It’s not in the song but one of the anecdotes about its inspiration involved The Kinks’ manager spending the night with a black trans woman in Paris so that may be where it’s coming from.
To be honest I’m on the fence about that too. Because “dark brown voice” can mean anything but being black. But for some reason people kept saying that so I just swung with it.
I loved that song as a teenager and had no Idea what it was about lol. Weird Al’s parody of it is really good too.
Walk on the Wild Side by Lou Reed
Josephine by terrorvision is about a guy realising that his roommate and friend is trans and that shes perfect wife material!
Transgender Dysphoria Blues - Against me!
How to Dress as Human by Laura Les
Girl Hell 1999 by Femtanyl
Anything Femtanyl is about as polar opposite as you can get from ukulele
Granted I’m mtf so that’s what I know most, but the punk and folk punk scene slaps: Pigeon pit, sister wife sex strike, left at London, against me, she/her/hers, gloss, murder person for hire, um Jennifer
Also Schmekel is good.
Folk punk would be filled with trans people. I say having quoted Pat the Bunny at my wife today
gender is boring by she/her/hers is played on a guittar, not a ukulele afaik
True Trans Soul Rebel by Against Me.
Fucking yeeeesssss. I listened to this so much one summer my wife asked if I had something I wanted to tell her
I assume the person is looking primarily for something in regards to ftm but for mtf I really like Miranda - Frank Turner (the lyrics make more sense in the context of the whole album though)
The town inside me and Like a weed, naturally, as a matter of course from guilty gear.
Dumbest girl alive by 100 gecs
Ugly cherries by Pwr bttm (band has some controversy and is no longer together)
There is an interesting song that has been circulating in the toki pona community. It’s a synth heavy cold wave song. It is a MtF song though so it may not be relevant.
Only potential downside for you that it’s in toki pona.
If you like angsty techno, patricia taxxon on youtube has a large backlog. As well as lengthy video essays about being a trans furry, or rants about obscure video games.
Sorry I don’t recall any specific songs by name that are about being trans though.
Edit: after making this comment and then going back to listen to some of her songs again, I’ve found out that there’s some recent internet drama regarding her. I will not make an opinionated statement on it here as I havent looked into it enough, this is just an FYI.
How about banjo? Sister Wife Sex Strike is pretty fucking dope lol
You can be your silhouette - king gizzard and the lizard wizard + mild high club
I’m surprised no one has brought up Travelin’ Thru by Dolly Parton.
Forced Gender Reassignment by Cattle Decapitation
Forced Gender Reassignment
I don’t think that person is trans , just tourtured?
It’s an allegory
Here’s one certainly not ukulele track by underscores.
