Visual Novels are super epic, so we should talk about them. Remember, no spoilers!
Anyway, my favorites are Katawa Shoujo and Higurashi: When They Cry.
Katawa Shoujo is about a boy who turns out to have arrhythmia, and after a long hospital stay, transfers to a school for disabled kids. There, he meets some girls that you get to date. Despite the idea originating from 4chan, this visual novel is super amazing and while I'm not disabled myself, I've heard it being praised for being great representation of disabilities. There are H-scenes (you can turn them off but you'll still see a few naked sprites here and there).
Higurashi: When They Cry is a kinetic visual novel that's split into 8 chapters (the split is there for a reason, and not just because Higurashi is long as balls). A boy moves to a small town from the big city, and makes some epic friends. However, things are a little bit sus... The characterization in this novel is astounding and man I genuinely felt terrified at points. There are some things you should look out for (there are two somewhat graphic flashbacks to a suicide attempt, and child abuse shows up too). The first novel is free on Steam. Remember to download 07thMod if you decide to play (it adds voices and the PS3 sprites, the Steam sprites are decent enough but suffer from a big case of boob clothing).