Arthur, you ask some good questions and none of them are easy to answer. To colplicate things, trans*women are as vastly different from eachother as any other group of people.
One thing to be clear on is that sex (biological) is different from gender (emotional/mental). You will hear Trans woman say the "feel like a woman", when in reality, language doesn't have an easy way to explain what this is. I find it better to say, I always UNDERSTOOD myself to be female. If I had never taken any steps to feminize my body, my understanding of my self would be the same. If a genetic woman gets a flat-top and wears a tux, she is still a woman - because that is her perception of herself. She is simply a "butch" woman, not a man.
Just as there are some children born without clearly defined genetalia (intersex), there are some people born with a mind/body disconnect. I can honestly say that my childhood as a "girlhood" - even if the people around me didn't understand that to be the case. For example, I always looked to women as my role-models - if a book or movie had crap female characters, I didn't like it. Boys, on the otherhand look to adult males for instruction and grooming - I rarely understood what it was they were expecting me to do/understand. Women, I got - men were the "other".
Here is a story - growing up, I learned that girls were nurses and boys were doctors. Getting that social message (untrue as it is) made me angry because I knoew that I could have been a good doctor and didn't "just" want to be a nurse. My male peers were not having that conflict, while my female peers were. When I enteed puberty, I was praying for a female puberty, because that was what my mind was expecting. When my father took me aside to show me how to shave my face, it wasn't a bonding rite of passage, it was a soul-crushing moment where I couldn't deny that my body was developing all wrong.
The above will only be true for me, and other Trans*women will likely have something totally different, but equally valid to say on the topic.
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