This reminds me of the song 'Tim I Wish You Were Born a Girl', although that's more about singer wanting the guy he was attracted to be a girl because he wasn't gay, but it's kinda close? '97 was a pretty different time.
I literally had this experience. I had a friend that I had known forever. One day we were driving back from some place after having a great time. He, in a barely audible voice, said something to the effect of why couldn't you have been a girl. I asked him about what he just said but he just pretended like it never happened. Never talked about it again.
Edit. I just realized this was a trans sub! My friend in this story is a cis straight man, I am a cis gay man. If this comment isn't appropriate for the sub please delete it! I was just trying to share a story.