A guy dressed as a woman and a woman dress as a guy is crossplay. If you're a guy and you dressing as Bridget from Guilty Gear, you are not cross-playing, since he is still a guy, despite what he looks like.
Though, honestly, I don't know why it matters. :/
Free - Soul Eater (Otakon 2013, Completed)
Goku - Dragon Ball Z (Otakon 2014, Completed)
Teen Goku - Dragon Ball Z (Otakon 2015, completed)
Powerline!Max - A Goofy Movie (Otakon 2015, completed)
Cafe!(neko)Kaneki Ken - Tokyo Ghoul (Otakon 2015, completed)
My Facebook cosplay group - Southern Maryland Cosplay
(Anyone can join)
Author of the "Getting Fit for Cosplay" Katsucon panel.