I’ve met one other crossdresser so far after getting in touch via another site. Definitely had a lot of fun — and got to try on a bunch of new clothes (and got to keep two dresses, a ton of panties, several bras, and a pair of high heels; all things that didn’t quite fit her and were just taking up excess space.)
Next time I will definitely aim for already being in girl-mode before meeting, though. I showed up in guy-mode and dressed up in the hotel room’s bathroom, which led directly into a bit of an anxiety attack where I tore off all the clothes and scrubbed off the makeup and went right back to guy-mode. Almost ended up just taking off right then, but managed to talk for a while and calm down and things got better after that.