Not quite despair (Iruma x Kiriwo) (Discontinued!)

When looking for a look of despair instead finds a look of embarrassment, though its not what Kiriwo wanted it still made him excited somehow.
After Kiriwo time in prison(whatever the demon jail is called) he decides to find out why he wanted to see that face again.

Is there more faces other than despair he yearns for or is it because of a certain person?

(WARNING: pictures are not mine)