I think you will really enjoy the book “Sissy” by Jacob Tobia. The author is smart and funny, and he touches on everything you mentioned and much much more! I’m just finishing it. It’s had such a positive impact on me that I’m constantly recommending it.
Additionally, here’s the link to the wonderful Ted Talk Jodie recommended today in another reply. It’s by a transwoman named CiCi, entitled “The Hardest Thing in the World.” Don’t miss it! https://www.youtube.com/watch?v=fw30yjccnD4 Only 15 minutes & excellent.