I would also ask. In fact, if not asking for things is one of your problems, you could see this as an opportunity to ask for what you want, see how he will react, see how that feels to you, and discuss that with him.
I did the same recently, a new T proposed a time for our intake session, and scheduled 3 hours for it. I asked her if that could be shorter, because otherwise I wouldn't be able to get my work done that day. I was happy I asked since I normally think of reasons why the other person would be angry/annoyed that I would even have the audacity to ask X, so that was one step forward to me. Also, she said yes and we scheduled a shorter meeting! I would change stuff about HOW I asked, but that's for the next time. Progress to me .

The safest context you can try out new stuff is with a therapist. Perhaps you can also see this as an opportunity to try out the things that are currently hard for you.