@kohaku lol no his name is ringo but the question says a guy who sometimes or always crossdresses so i was just clarifying that it was always. @jaychan yea me too! (well one of them hehe)
Akemiya from Sasameki Koto XP He's actually a model (well he WAS a model until *SPOILER* he got pantsed while walking down the catwalk and his true junk was exposed).
It's not so much an always or once more like when his sister wanted him to or when he was modeling. Which was pretty much always.