The way I read these examples, I think he is reacting a little bit like an older relative who finds the things a younger relative is saying to be endearing. I don't at all get a vibe like he is mocking you in any way. I think he is appreciating your candor or directness.

I don't think that means he sees you in a condescending way. I think that, just like clients sometimes get transference and start seeing their T as a bit like a parental figure, T's probably get transference too and sometimes feel protective or appreciative like a parental figure might. That stuff can happen even if it doesn't quite fit the data (i.e. your ages and so on). Just personally, I would tend to see this as a positive sign that he likes you as a client. That's just my personal read on things, from your examples.