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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.
Josephine by terrorvision is about a guy realising that his roommate and friend is trans and that shes perfect wife material!
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!
