I've been living as female for a long time since I realized I was male--I actually halfway tried to transition in middle school, but of course I didn't have any resources on being transgender, and didn't really understand it as a thing.
I'm really afraid of losing my relationship with my father if I come out. Ironically, we're very father-son-ish, but he's bad at being an advocate for himself and his children in the face of my family's overwhelming pressure to conform. In private he's quite affectionate and really enjoys my boyishness, we're almost like brothers together, but when I'm at family gatherings I think he feels strange being responsible for me, since I don't fit in at all with the rest of my heteronormative cissexist somewhat racist Southern family. I know he would feel put-upon and awkward explaining my "condition" to the rest of the family, and I think he might distance himself from me about it for a while because he can't deal with having feelings.
He also expressed a lot of concern for my personal safety and career prospects when I told him I was bisexual, so I think he'd want me to become comfortable with being a woman so that I would not face so much trouble living as a trans man.
My mother knows I'm not just female, because she's been there all my life and witnessed my asking for a penis in nursery school and dressing as a boy for several years, etc. But she really dislikes androgyny and I think she has a lot of trouble dealing with my being someone other than her.
Blah blah blah my family sucks. Anyway, more specific answers to questions:
What do you find the hardest part to be about having to live in society as female?
Getting called ma'am all the time, especially as, living in the South, it happens constantly. I can stand being looked at by guys and treated a bit like a lady, because I'm a really girly guy and I can tell myself they're attracted to me as a pretty boy, but ma'am is the worst kind of misgendering to me, because it always sounds so condescending and like they aren't even vaguely supposing I might not be totally cis and female.
What about appearances ... do you still look more female than male?
Hopefully I'll always look kind of girly/femmy. Since I'm not on T and have gained a bit of weight, my face is a bit too girly for me, and I've got enormous breasts I want gone (and large hips too.) So people read my body as female, especially here where I have to wear warm-weather clothing and where androgyny is not usually read as such. This frustrates me. Other than wanting to lose some fat and bulk up some muscle and lose the tits, I'm kind of okay with my looks, I just wish people saw me as "woah really girly dude" rather than "oh kind of dudely girl".
Dress male or female?
I'm wearing a skirt from H&M right now, dude, I think that answers your question.
For parties, bars etc I'll present more like my real self. I go to drag king shows in a binder and with clothing that maximizes the more masculine parts of my body (broad shoulders and chest, long legs), and when I have to go to funerals and other official-ish occasions I wear a lot of black lace or brocade with pants, in a way that is still very queer rock star even though I have boobs.
Does having to "play the part" ever wear you down?
Oh, all the time, but especially around my family, my mother in particular. It's very tiresome to invent excuses for why I want relatively normal guy things, like swim trunks or 'violent things' which weren't considered appropriate for a girl. And I'm very often jealous of my younger brother, not so much because he's cis but because my parents treat him like a boy without his having to fight for everything.
Do other females trip you out in any way because they think you're "one of them"?
Mainly it's just when they refer to "just us girls" or something, including me in the group. Also, very conservative women will change in front of me, which weirds me out.