I used to sing a lot; I sang in school choirs from 2nd through 12th grade. (My high school had eight different choirs!)
Like most everyone who has gone through a testosterone-powered “male” puberty, my “natural” voice is sort of low and masculine. My vocal chords have been physically changed, including them being longer than before. Feminizing hormones — usually estrogen, plus a testosterone blocker like spironolactone — reverse some effects of testosterone, but changing your voice isn’t one of them. It’s a one-way street. (Boobs are too, in the other direction. Most trans men want top surgery because testosterone doesn’t fully reverse the effects of an estrogen-caused puberty.)
So I (like most trans women) end up trying to change the sound of my voice through conscious effort to sound more feminine. It’s a bunch of work and only a partial fix – you can only change your voice so much. In my ideal world I’d sound unmistakably feminine, but I’ll settle for not sounding unmistakably male so I don’t get “sir”-ed on the phone, landing in a sort of androgynous middle. Because my vocal chords have been stretched out, I can’t sing (or speak) high like I used to.
And so I realized that when I’m singing this is more of an issue than other times. I think for two reasons: first, songs tend to have a much wider range of pitch than spoken word (so hitting the edge of my vocal range is more frequent and more noticeable); second, when singing along to a recording you have other audio as a reference for what pitch your voice “should” be. I realized that this makes me feel Bad.
“Voice feminization surgery” actually is a thing. Where they physically operate on the vocal chords in your throat. (There’s even a laser-powered kind that’s less invasive!) But unfortunately today’s techniques aren’t great for singers. They can raise the lower end of your range but aren’t able to also raise the top end; I think they can also make it more difficult to sing within that range. And I’m not ready to accept those tradeoffs so I’ll just stick with the status quo for now. Maybe they’ll invent something better.
I used to love karaoke. I kind of still do but my emotions are much more mixed now because gender dysphoria nags me whenever I try. Oh well. Realizing that I’m trans and going through with my transition has still been 95% good. Guess it can’t be perfect.