Not sure if this helps but usually if I think T (or anyone else) is going to judge me, I start off by first saying that I'm feeling terribly vulnerable / ashamed / hesitant to say this etc -- so, kinda prep the ground and then start to talk about whatever it is.

Doesn't always work of course (with some people it flies right by them) but with T, I have noticed that she's usually extra / super gentle when I start off by saying that.