“King for a Day” by Green Day is about a crossdresser, although the subject doesn’t seem to be actually trangendered.
“S-E-X-X-Y” by They Might Be Giants might count. Like a lot of TMBG songs, it’s a little hard to interpret, but does include the line “She wants to be a man.” This thread isn’t limited to M-to-F, right?
And as a big ole lesbian who mostly dresses in male clothes and who watched a close friend go through an agonizing M-to-F transition, we are just laughs a minute, lemme tell you.