When is the line crossed for good?

At what point s crossing the line that a male becomes something other than a male?

  1. Putting on first pair of panties / thong?

  2. Crossdressing / wearing makeup?

  3. Going out in public en femme?

  4. First dose of estrogen?

  5. First time kissing as a female?

  6. First time sucking cock?

  7. First time getting penetrated?

  8. First feminizing surgery?