Just going to throw in some of my thoughts too:

1) Explaining feeling judged, or anything else really: I think it's always useful to use examples when someone doesn't understand. For your T, it might be good if it was an analogy from sport. Something like the pitcher thing that was mentioned before. Other possibilities might be examples with children (such as a child feels judged if people laugh at the child for wearing a certain thing), you can bring an example and then explain that this is how you feel in certain situations.

2) I think his reply shows he did understand what you meant, but maybe he doesn't quite want to do the same thing as you. I'm not sure what you'd mean by 'accept and join me' though. I think he shows that he is willing to accept the fact that this happened for you, and that you guys need to talk about it for extended periods of time. But at the same time, he worries about you getting too dependent. It's a fine and difficult line to walk, but a very important one. My T (who's very comfortable with working with transference) once said that it's very difficult to know whether the T is encouraging dependency with his behavior, and it needs to be reevaluated a lot, thought about and sometimes the T has to limit some things in order to not create dependency.

I think he understands why it's important to you to talk about and work on. Do you understand the reverse, why it's important that you also work 'against' transference? I know that for me, being dependent on someone is a very comforting feeling, it feels much more natural than being securely attached. But if my T just let me develop transference like crazy, it would ultimately not help me, because I'd just repeat the same things over and over. I think that's what your T meant, that he needs to think about how you guys can at the same time talk about it and work through it, but still not get you to a point where you're too dependent. And since he's not that used to working with transference, that requires some thinking and planning on his part.

3) I think the issue for me would be that he'd share too many feelings with me in this situation. If I told my T about a situation in my life and he said it made him uncomfortable, I'd worry about HIS feelings. Sometimes it's alright to share feelings, for example if he's truly worried I might hurt myself (sharing will make me more likely to not do it) or if he shares a certain emotional reaction he might have in a similar situation (either because I can see I'm not alone, or because I can see alternatives). I think being honest is good, but not sharing anything does not equal being not honest. It's like if you have a bar of chocolate on the way home, and don't tell your husband about it. It doesn't mean you're not honest, you're just not sharing it, and if you were asked directly you'd probably admit to it.

I'd tell my T in this situation that although I appreciate that I have an effect on him and that he wants to be honest with me, honesty does not always help the situation. That he should be careful to share things with me that are not necessary. Because ultimately, it's about me. If he's not comfortable with something, he can seek supervision. I don't need to know about that part, it does not help me in any way. It's not my place to deal with that feeling and I don't have any expertise in it either. If it is not beneficial to my therapy, it doesn't need to be shared, even if it were honest.