Just a heads up this is an anti trans joke. Not saying you're consciously bigoted, but your punchline is literally "I'm trans!" which is fine if you're going for that, but I'm guessing you're not, and it's also not funny unless you think being trans is funny in and of itself
You don't know his story.
She is Indeed very pretty but that is the most horrible look ever. That look to me says, "Dear God I am stuck doing this shit for the rest of my life?" I know this look this is the look of someone who makes McDonald's a carrier. This is the look of someone who is trapped in something they really do not want.
Like Princess Diana