I can't say that I have.
I did crossdress as a guy with a bowler hat last year...so I guess in my situation I did the opposite...i dressed as a guy for sh**s and giggles.
If you want to dress up as your true gender then go for it...but a lot of transgender people have done this method (dressing up in the other gender hoping others will think it's just for Halloween but it's something more) for so long that if you have transgender people there they will know. But either way...who cares. Just have fun.
I'm not into the ty look at all. Transgender people get enough crap for being associated with a ty behavior, wearing skirts so short people can tell what religion you are, thigh highs with visible stayup bands, and stilettos that are so high people look like an ostrich when trying to walk in them...I would never fuel that stereotype...even in good fun. But to each their own.