During all of my years, it's became abundantly clear to me that I have a problem with trusting other people not to do me in at the earliest opportunity. It's pretty clear to me why: when you've been taught by the whole society, by everyone you know and love, that you are something, and you then, on your own, find out and realise that they all were wrong, it's pretty hard to trust anyone much afterwards.
It goes deeper than that. I had this trust problem already as a child. I don't think it's completely outlandish to think that this was due to a persistent cognitive dissonance between what other people expected me to be, and what I actually was. I couldn't fulfill the expectations made of me, and it wasn't a question of being somewhat imperfect. I just failed at sex and gender. I recall clearly wondering what was wrong with me, why couldn't I figure out the way boys are supposed to behave (it wasn't for the lack of models, or for a missing father, or any that creepy ex-gay -shit - I've had an unbroken home from the day I was born, with both mom and dad and all that stuff), and infinitely sad because I couldn't fit in, no matter what I did. I knew I was different, I just couldn't put my finger on the exact reasons why.
But when I did figure it out: after the first rush of relief came almost uncontrollable anger, and fear. These guys had conned me all my life! And not only that, but some of them were crazy enough to police my behaviour with violence (cheers and beers, my classmates from comprehensive - hope we'll never meet) - as if not conforming to the sex assigned to you at birth was such a huge crime against them.
I also started wondering at a few things. I was pretty damn visibly non-conforming during my teen years. Why wasn't I referred to anyone? Was it because I was otherwise a well-behaved girl, who did not cause much trouble? Or was it because they knew there was nothing they could do - or because they didn't dare to, or because they thought I was beyond their "help" anyway - help in this last case meaning forcing sex and gender conformance (it was rather obvious I wasn't going to conform that way).
What it boiled down to was that no-one helped. I was left to my own devices, and that's the way I've been going on ever since. Going back to trusting people comes very very slowly, and so far I've managed to trust just a dozen or so people (you know who you are and I love you to bits). And it's the hardest thing for me to do, it's harder than transitioning and all that.