I am in a very similar situation to yours (adhd + autism), and just wanted to say that most of your experiences line up with mine even the tabletop rpg stuff (although i havent dressed feminine before in a social setting). as the only place im actually out for being trans is online; and havent dressed up for any dnd/events before.
But personally i feel like the most important part here is "if i could be a woman without consequences i would" which is the reason im only out in online places.
because i personally dont have gender dysphoria; just gender euphoria when gendered as a woman (and i think you aswell but i cant speak for you but that is my gut instinct). So i don't mind going through life as a man because i fear the work i would have to do to change would be more annoying than just keeping the satus quo. but for you seeing as people complemented you dressed feminine might not be as big of a barrier, as you seem to have great people in your social circle.
apologies for grammar or typos currently writing on a phone while slightly drunk and dyslexic. if anything isnt clearly written let me know but i already reread this 3 times >.<
in the words of the great Timothy Dexter: "salt and pepper these as you see fit ,,,,,,,,......'''':::;;;;"
nah he was fucked before all this happened you don't become the richest person by being an upstanding moral human being.