There is, or at least was, at least one place catering to your friend's tastes: https://urnotalone.com/male-maids-serve-it-up-at-japans-first-cross-dressing-maid-cafe/

Edit: More recent article: https://www.tokyoweekender.com/food-and-drink/restaurants-and-bars/boys-magically-become-girls-at-the-maho-ni-kakerarete-crossdressing-bar/

Those are butler cafes unless you mean crossdressed guys in which case I've no idea.