I have skipped sessions couple of times. My T was ok with that. He waited for me to raise the topic next time. I assume that if I hadn't mentioned it at all then he would have found a way to address it at some suitable moment though.

To be precise, I've skipped sessions two times, which were two days in a row and I was actually out of town but I preferred not to tell him. On the third day I could not resist anymore and called to ask what he was thinking about me not showing up as I had never missed a session before.

On another time I was travelling and I did not tell him again. Then I called him again but just about 5 minutes late, so he would have had the chance to start wondering what's going on with me (because normally I'm never late).

The money part is similarly a non-issue - my T has no cancellation policy what so ever and so I will pay for all my sessions anyway, whether I show up or not.

It seems to me that your T's reaction is very normal. For some reason you need to do it and then later you can talk about it.