LT, it sounds like you have a tendency for wanting to know exact rules and worrying a lot about not doing everything properly - that can definitely be part of perfectionism, OCD, call it whatever. But also pushing those limits when they are at least somewhat defined Perhaps your T does not make them super straight and clear on purpose? Dunno, it just reminds me of something my last T said once when we were briefly discussing boundaries in therapy. He said that he did not like to set anything in stone, more go with the flow and adjust on the go. He thought that strict boundaries usually have an effect that people want to push and test them, often just for a sense of momentary accomplishment that they are able to affect someone else's boundaries. I personally agree with this, not for everyone as there are indeed people who want to do everything by the book, but many find it rewarding to challenge existing rules and boundaries. I definitely do and this is only one reason why I usually work better with people who are reasonably flexible and adaptable, not just Ts but in general. That also means sometimes we learned the limits by pushing them and I think that is okay if not too aggressive - I would just trust that the T will tell you when something is too much. Your T definitely seems direct enough for that, so I would really just leave it for him with the outside contact stuff, fee, etc. You know, just like when he said he trusts that your own judgments about your needs are reliable. I think when someone reasonable expresses that an act is too much and they want to participate differently, it most often does not mean they are mad or do not care at all - they merely share their side of the construct and negotiate.