Here is Greenwood (2008)

It seems like 15-year-old Kazuya Hasukawa's life can't get much worse. Not only did his older brother marry Kazuya's first love, he brought his bride home to live with the family! Forced out of his own home, Kazuya enters an exclusive all-male boarding school, Ryokuto Academy. Unfortunately, a prestigious education is little compensation for getting stuck with the cross-dressing roommate from Hell...