I am a MTF post-op who presents mostly female / androgynous (no skirts but women's clothes in general, makeup and nail polish and such), and I live in Italy and travel all over the EU. For the most part, I pass when I want to pass, although I'm quite tall and so always get interested looks. As far as Italy goes, it can be divided into 2 parts: north of Rome and south. North, especially in Florence, Milan, and Bologna, there is a thriving LGBT scene and you won't have any problems. Let's just say I haven't gone south of Naples in a long time, however, and Sicily is off my travel map for good. Other places in the EU shouldn't give you any problems, although I'd watch it in Moldova, Bulgaria, Serbia... generally the more east you go. Overall, so what if you're traveling with an M on your passport? I do, but my photo is with make up... as long as you match the photo, you'll be fine. It isn't anyone's business at immigration why a "male" chooses to look like a woman, so long as the name and photo match. In Russia, I wear men's clothing and go butch, so the immigration there actually gave me an issue, but it was more curiosity than anything else. As anywhere, late nights in big cities at mixed bars can get people like us into trouble, but as a regular tourist, you'll be fine.
