Let's see... How often do I detect some reaction from someone that indicates they've just seen a crossdresser? Almost never. How ofen do I truly pass? Almost never. The only thing I truly pass as is a nice person who goes way out of her way to look convincingly like a woman. That's what I am, and that's all I am.
I openly crossdressed for several years before I first came across someone who OBVIOUSLY read me. I was in my mid-20's, very skinny, mid-back length roller-set hair, stylishly dressed in a skirt suit (my wife's). To me at the time it was undetectable that I wasn't a woman, an opinion expressed by my wife. I agreed. I won't go into the whole story, but I was quite shaken by this revelation that someone, anyone, could possibly tell I wasn't quite what I pretended to be. In the mirror it was still undetectable. I've been around long enough to know now that this was just delusional. I saw what I wanted to see.
I think the prevailing public opinion of me would go something like, "I'll be damned! There's a guy dressed like a girl, and it's not nearly as repulsive, threatening, or off-putting as I thought it'd be!" That's about all I can hope for these days, and that's quite enough for me.