I think it might be an issue of reframing.
Of course he has boundaries - I'm sure he doesn't go around hitting people in the head with a hammer and whatnot. But the kinds of boundaries he does respect, he probably doesn't think of as BOUNDARIES. He might have an association with that word, and other words like rules, structure, etc., that he feels he must resist and rebel against. For some reason, he finds being required to obey some sort of orders from outside himself as offensive, unnecessary, or what-have-you.
But that doesn't mean he never plays by the rules, he has just reframed the rules and boundaries he does accept as something other than rules and boundaries, or something that is more beneficial to him than not working within those boundaries. The trick will be to find what elements he respects and a way to reframe the boundaries you need as something more palatable to him.
Hot chick in the city.