Bleh this is how I feel, with different genders. Everyone 100% treats me like a girl. Besides dressing in a kind of "tomboy" way and being ¯\_(ツ_/¯ about what I'd call "feminine habits" (fussing about make up, clothes, hair, etc) in conversation, no one, no one, is ever like "Oh yeah, Tomita's so masculine/boyish!" Never even "tomboy" beyond the clothes thing! I must act like the most submissive chick in the entire fucking world. And I look five years younger than I am, and I act like a dumbass most of the time, so it just compounds everything. One time someone online said I "sounded like a guy", but that's honestly bullshit, because you really can't tell someone's gender from their writing. That's a 100% bullshit myth is my understanding. So how am I supposed to be trans when, despite trying, I still act pretty much 100% feminine? Or am I just thinking about it too much? I honestly don't think I am. I think me going down the transsexual route is a fucking delusion on my part.
The most I can say is my sister thought I was a lesbian for a while and probably thinks I'm being "delusional" about being bisexual, and I'm just totally lesbo. Except no, I really am bisexual. My dad might wonder if I'm lesbian too? Not sure. My mom is fucked up and has fucking problems. She asked me why I cared so much about LGBT rights so I had to admit to her I was bisexual, and she shoved me back in the closet. She constantly emphasizes to me that I will TOTALLY get a husband and make grandbabies whenever the subject comes up, I think as a response to me "coming out." (And no, I never told dad about my sexuality, I honestly don't know if my mom would blab to him, but he's not fucked up like my mom and I don't want to ruin our relationship in case he's a surprise homophobe, bleh.)
tl;dr I get "lesbian" points from my family but I highly doubt that counts and also my mother and sister are fucking terrible and abusive so that's not exactly a confidence boost.
There's a good chance it will always be harder with people that you know before transition than the ones you don't. Don't get me wrong, people you already know can "get it" too, but it's the sad truth that those that you mostly know post-transition will probably have zero trouble seeing you as a guy, even when they know you're trans, and those that knew you longer will struggle to shake their perceived image of you, or sadly not even try. Even long after my friends had dealt with my transition and no stranger would ever really gender me male, there still remains those that haven't tried to understand, and refuse to believe that they are the ones with the problem(my sister even asked me if I was trans a year before I came out to her or any of my family, but became incredibly obtuse during transition).
The important thing to remember is that you don't need anyone's approval. Just concentrate on those that accept you as you and be ready to cut ties with anyone else. When I was first considering transitioning, going to LGBT group therapy through my school and later GLAD meetings were immensely helpful for making me feel like I had a support structure at a time where I wasn't sure who I could talk to, so try and find a space where you can be comfortable and go from there.