I think this may be the place to impart some long boarding wisdom. On sunday i bailed at about 30mph coming down a hill...i'm told it was quite spectacular, but you know what, I rolled into the fall, bounced back up, asked if the board was okay, then my sunglasses, then went owwwwwww! Twenty minutes later i was back on the board, and an hour after that I hit another hill where i got up to similar speeds, and as i was taking the corner I picked up some speed wobble. I could have bailed again, but i kept at it and rode it out and it was awesome. See the thing is, i throw myself down hills on what is essentially a plank of wood with wheels, I accept that i may crash and as long as i can get back up on my feet i won't give into the fear of crashing. I'll get back on the board and conquor that fear. Bailing does hurt, but it's not the most important thing about longboarding and i certainly don't worry about it.
It's the same with being percieved as your correct gender, if whether you "pass" or not is always on your mind, then you're scared that you might not, if you're scared that you might not then you are giving into the fear. Which makes you nervous and people pick up on nerves and ask "why are they so nervous" and go looking for answers. Transitioning is hard, but you know what, chances are you will be mis-gendered from time to time, but you know what, that happens to plenty of cis people as well. All you have to do is roll with the fall, get back on your feet and carry on going, because if you can do that you'll be relaxed and if your relaxed you can truly enjoy being you. And if you truly enjoy being you people just accept you.
My advice for anyone transitioning is basically, by a longboard and learn about how to deal with the tumbles life sends your way occasionally that way, because the times when you're not kising pavemnet are simply sublime.