Masaki Akemiya' is a character from Sasameki Koto.
Masaki is a shy and timid boy, who displays aspects similar to that of a girl.
His overly attached sister sends a picture of him cross dressing to a fashion magazine, he oddly enough gets chosen. The other girls don't see him as a boy, rather just their pet.
Reason For Cross-Dressing
Masaki loves the main protagonist, Sumika, however she is clearly in love with a girl. He decides to cross dress in order to gain her attention.