I like a lot of the points Xynesthesia made. I also think it would be a grave mistake to think that a T without adequate training and supervision can get into deep transference-based work, even if both the therapist and the client want to go there. It's a potential minefield in the best of times and seems foolish and dangerous to attempt without adequate preparation, no matter how flexible the T wishes to be.

My T shares her feelings when she thinks they will be helpful for me, but it's an incredibly delicate balance. Your T seems to not have that inner monologue or instinct to know when to share and when to hold back (hence the feeling judged bit). It seems like your T isn't able to understand why you feel judged when his intention or feeling in the moment wasn't one of judgment. When my T's message gets garbled beyond recognition, it is almost always because there is stuff from my past or my view of myself that's getting in the way. My T can often sense when that is happening faster and better than I can (although I'm getting better at it as time goes on), and she's usually good at drawing those links to people or events from my past. I wonder if that's something your T will be able to notice and work with better once he has a stronger grasp of your history. Or maybe not. I don't always think it's helpful for the T to go into great detail about what he/she meant or felt in the moment (beyond saying that X thing wasn't meant negatively) because the thing that happened sometimes actually had very little to do with the therapist him/herself.