I wish I knew where the line was
What could I ask for and have before you started to deny requests?

I don't want to do trial and error, because crossing that line even once would make me feel so humiliated and angry at myself for having asked.
There was one thing I asked for that you said no to. That was over a year ago and I still hate even remembering.

But, as you know, I still need the line to exist. I trust you to keep it on the fairly rigid/professional side of the boundary spectrum.
Getting what it feels like I want would ruin this entire thing.