As a kid it was easy for me. My mom was a housewife and at the same time a second-wave anti-porno etc. feminist (

). She thought I should have the freedom to be myself without putting me into gender boxes. And my dad had grown up with a cross-dressing tomboy sister kid in the 50ies/early 60ies who later turned out to be a butch lesbian (as a kid, she always wore male carnival costumes, mexicans, cowboys etc. whenever she could, she had at least a dozen of them. This was the only "male" option offered to her by her mom and she made a lot of fuss whenever anyone tried to stuff her into a dress - meanwhile I suspect she's not just butch, but trans, there's a lot of clues for that...). My dad thought I was like his sister and would become lesbian and he did not worry about me. Whenever anybody else then said to me I had to act like a girl etc. I just got angry and said I did not care and did whatever I wanted. I played with both girl and boy toys at that time, did not always mind wearing dresses but usually refused them, and did risky stuff such as climbing up high trees etc.
I was the only French immigrant kid I knew of, among Germans and Turkish etc. kids, and I thought that me being raised as a girl though I was a boy was maybe a ... French thing to do with boys, if you did not want your boy to be pressured into strict gender boxes too early. Cause boys get much more pressure there. And therefore my parents denied that I was male though I knew I was. I played the game though, as I enjoyed being less pressured than my male pals. And maybe some French male kids had something wrong between their legs anyway and this would become normal later.
Then puberty hit and with it, the pressure to conform. My body really developed into the body of a woman. ->-bleeped-<-. My mom outed me as lesbian, making a huge scene with bursting into tears and "I don't want you to become a lesbian" before I was myself aware that I was in love with this girl. I was so shocked at the moment, I did not know how to react. It was at a time of my life where I was suicidal anyway, for other reasons. Never talked to my mom again about this, but it shunned me away from wearing male clothes for a long time... did not want to be confused with my aunt. Did not want any other scene at home. I'm no lesbian. I'm bi. And I'm a guy. If lesbians wore male clothes, then boys in female bodies probably didn't do this I thought. So I went for drag-like and neutral clothes.
Everybody in my class took dance courses, but I just couldn't. I found it silly that the boys had to dance it differently than the girls anyway. But I found it completely unacceptable to learn the female dancing steps there. I just could not stomach this. At home, I got a lot of ->-bleeped-<- from mom for my "male body language", she meant well and just wanted me to fit in better. I got very angry at her for her remarks. Dated a guy, but this did not make me any more feminine. I was clumsy, and she suggested to me I should take ballet courses to get a better body language. She was right, I was clumsy and I got her point and found a martial arts course and asked her to pay for it. God was she angry. Martial arts are not for girls, much too brutal. (

?) I told her I want to defend myself and be less clumsy and didn't she as a feminist want me to be able to defend myself? And then she went like okay, grudgingly.
Hate all those useless fights with my mother in teenage years. She just couldn't cope with the fact that I did not evolve from a tomboy into a "woman" as she had in mind but just - into me, as I was. My dad never made trouble there, he often kept out of this silly fight or did not know it happened, and sometimes tried to temper my mom.
Late teens to mid-twenties. Moved out of home as soon as I could. Still behaved however I wanted, but still wore either androgynous or female stuff. Then again, some of that female stuff was really hot to wear. Outed myself as trans to a couple of persons, but that was no big deal there, as many of them were at least genderqueer.
Mid-twenties to 30 Met a guy I fell in love with. Really nice guy, but close-minded, homophobic straight... need I say more? I am still angry at myself for having dated him at all, it was a waste of time for both of us. He kind of hindered me from... being me. But I could never be the woman he wanted. It just did not work. He even came to me with a dance course for both of us, I refused it, told him I cannot imagine a dance course where the steps are different for men than for women and I make the female steps. He was like:

Etc.
At work, was in female attire, but not normal, rather extreme, drag-like stuff. Sometimes even my boss had to grin as my body language etc. was really male and I looked like a drag queen in these dresses. And I told him, I'm not really a female and cannot be that, I'm just who I am and cannot hide it away. He did not know exactly what was going on but could sense it.
Since then:
Started transition. Much of this crap got a lot better since. Occasionally I miss the opportunity to wear drag, but it's not a strong feeling...