Lola by The Kinks is about a young guy losing his virginity to a black trans woman. Don’t know if that counts.
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.
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.
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
Transgender Dysphoria Blues - Against me!
gender is boring by she/her/hers is played on a guittar, not a ukulele afaik
All albums by Marie Dior
Two songs. Not about being trans but accepting someone you love being trans
Aaron by Palehound Task by Great Grandpa
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.
I’m surprised no one has brought up Travelin’ Thru by Dolly Parton.
Anything by Glass Beach (two fantastic albums by the way)
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)
I think the whole album Wallsocket by Underscores has a trans undertone. Maybe I’m reading into it to much but the artist is trans.
Banger either way tho
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.
How about banjo? Sister Wife Sex Strike is pretty fucking dope lol
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 a bit more sense in the context of the whole album though)
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