Hourou Musuko

Title Horou Musuko translates to Wandering Son. The 2002 manga series is still ongoing and has amassed 12 volumes. It is about a transgendered boy named Shuichi Nitori and girls he is friends with in middle school and various romantic problems that occur with them all, as well as difficulty in fitting in while crossdressing.

A 12 episode anime adaptation was made in 2011.