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I go out with a bunch of local CD girls a lot.
I was in DC, in full boy mode, and as I'm walking into the Metro station, I hear this guy calling me from behind. I turn around and he walks toward me and says (quietly), "Are you Steffi?" As I'm trying to process this information, he says (again quietly), "I'm [girl name] C." At just about the same time, my facial recognition program finally finishes processing the inputs and I say (again quietly), "Oh, Hi C. I didn't recognize you at first." I look behind him and see K (in boy mode). I still missed A who was standing right next to K (also i boy mode).
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When I was younger I think the transformation concealed my male ID more than it does now that I'm older. There doesn't seem to be any rhyme or reason to getting clocked though. I've had people who know the guy me well fail to recognize me, but get clocked in a heartbeat by a casual acquaintance. Maybe it depends on the setting or context, or maybe some people are just more perceptive than others. My advice is, if being outed is of concern to you, don't let not getting clocked once lull you into believing it will work every time. For most of us I think the odds are 50/50 at best.
One bewildering phenomenon I've experienced on two separate occasions with two different gurls ... In both instances I met them online and it took a long correspondence to persuade them to take the plunge and go clubbing with me. They were nervous as a cat in a room full of rocking chairs. But we get to the club and they find out the world isn't coming to end, they have a drink or two, start calming down and enjoying the experience, when lo and behold someone they know walks into the club. At first they freak and I suggest we can leave if they want to but some sort of weird fascination sets in and they sorta started obsessing about it until suddenly, much to my astonishment, they stood up, walked over to the other person, who had shown no sign of noticing or recognizing them, and outed themselves for no apparent reason! I have NO idea what that was about! :-O