Kaichuu!

One of the Character acts and dresses like a girl and they both hit on a particular boy. They will do whatever to make them theirs. Both very funny and interesting animes.  

Both are short anime about master archers. While To Shoot Without Shooting is more historical, Kaichuu is more comedy. 

Both have cute cross-dressing boys 

Both of these animes comedy and contain cross-dresser 

both animes are cross-dressers because of their grandfather's wish. 

Both of these animes contain someone who is Transgendered.