If you mean Nukige, then not. If you mean a serious VN, I believe that If My Heart Had Wings was the first one (in all the possible way, meaning that was the first VN that I've ever played back in the days) that made me seriously cry, and develop emotions that I thought I would never feel for invented char.
The second one.. I suppose could be Grisaia, the first - since I've yet to play the other two, the side-stories.. and even finish the first one honestly. So maybe I shouldn't properly say the VN, rather the Anime adaptation because even though most of the routes were obliviously cutted to fit right in 24 episodes (were 24, right?), this still made me feel... bad.