Me in a dress, that's a topic of its own. I was wearing this hippie style dress 15 years ago, no make-up, and a group of teenage boys was walking behind me and I heard them argue whether I was a female or a ->-bleeped-<-. ("he's got broad shoulders, it's a ->-bleeped-<-", "look at the silly ear rings, it's a he", "she's short, it's a she", "short hair, it's a he", "look at the way he walks, it's definitely a he") They finally agreed that I was a ->-bleeped-<- and harrassed me verbally which made me grin more than be upset, first because at least I had some passing, second because have you ever heard of a hippie style ->-bleeped-<-?
Though this kind of encounters was not nice, I always had more trouble passing as male in male clothing than when I wore certain female clothing before T. This could bring me into this kind of danger, though, so I did not wear that stuff often.
Before starting T, I just couldn't resist taking a couple of pictures of me in drag and with trashy make-up (make-up always looks trashy when I do it). I posted them on a ->-bleeped-<- website and ask for comments. They thought I was a bio male and complimented me for looking good "en femme" and asked me how I did it.
An MTF friend of mine had been going to ->-bleeped-<- meetings for a couple of years while still figuring out what the heck was up with her. During her transition, she wanted to go there again meet old friends, and she asked me if I'd go there with her. I was like okay, but I want to be dressed appropriately for this event. So I organized a red 19th century western dress from a life roleplaying friend, and she did the make-up and provided jewelry plus a wig. It was hilarious. I had been on T for 6 months and looked ambiguous at that time. At the event, I was asked by several ->-bleeped-<-s what I was ("Sorry for asking, but... are you a man or a woman? We just keep wondering there at my table."). Other TVs just gave me confused glances the whole evening until word spread round.
Funniest thing about that evening was that my MTF friend and a transitioned FTM acquaintance ended up at my table and after 2 hours of chatting, they outed to each other. Before, he thought she was a bio female and she thought he was a bio male.
Oh, and whenever I need to show my ID (not changed yet) or have to out myself as being transsexual for other reasons, people always ask me if I still have something dangling there or "had the OP" and was officially a woman now. Which is kind of silly if you have a 3-day beard and male clothes and haircut, but it's funny.
