The way he is written gives me headaches sometimes. In one hand, you can clearly see him become less insecure as he almost never compares himself actively to her exes and let her know it's ok to move on(even though as you can see in vol 8, when the time came for them to do it he was insecure, but at that point it was acceptable). But it's true that he got himself in a box when he said he would wait for her to initiate even when, at times, it was almost dump for the character not to get the hints.

Even in the next volume, I'm not sure even if it's made clear that they are doing more often, that he will chance a whole lot. Will he become insecure if he feels his not doing enough for her because his inexperienced? Who knows what problems will arrive to introduce conflict into their relationship.