Typically behind his back, he only really finds out in the bad end. That being said, while there is a bad end for enemy encounters (hobos, troll, goblins), there has yet to be an ending to this game.
Which is really quite a bummer, I kind of want to double down on the story itself. It seems like it's going somewhere big, but we've been so preoccupied with porn that we're not getting any closer to the story. (I say that but we recently got the Iris content which probably progresses the story)
Would personally like to see where the story goes and then have porn branching off of that, so we have more variety as far as locations, situations, clothing, etc.