Cross-Dressing Voices

Anime

 * Kazune Kujou is voiced by no other than Miyuki Sawashiro of Kamichama Karin.
 * Ciel Phanthomhive in Black Butler is voiced by a female in both the original and the English dub.
 * All the male characters in Simoun are played by women. (Although given the nature of the show, that shouldn't be a surprise).
 * Fushigi Boshi No Futago Hime: Of the 6 princes on the Wonder Planet, only two (Auler, Bright) are voiced by guys. Junko Minagawa is the voiced of one of the others. In season 2, one of the new princes is voiced by a girl, prompting a bit of gender confusion at first when he was originally listed as a princess (his hairstyle didn't help any).
 * Despite being a teenager, Satoshi from Higurashi: When They Cry is voiced by a woman. Keiichi is the same age as him and averts this trope.

Western Animation

 * In Duncanville the main character Duncan Harris is a 15 year old boy voiced by series co-creator Amy Poehler.