My therapist was great. Our meetings were through the net too, and it was wonderful to be able to meet with someone since there was literally not a single therapist in Alaska that would meet with me. My therapist was not just a gender therapist but worked with a varied client base so she had experience dealing with a lot of different issues, which was awesome.
We discussed just about everything. I was seeing her to get my hormone letter but we didn't just stick to trans issues. We basically went through my life to start with, and talked about somethings that were not exactly comfortable, but we also talked about my classes, life goals and even things like hobbies and favorite things. She felt more like a friend than my therapist. I don't keep in touch with her, but its mostly because of the time difference with her being half way around the world. When I was seeing her, I talked to her every week until I got my letter and once I started hormones it was every two weeks until I left the country.
My only advice is if you feel a connection with your therapist, be honest. Not every therapist is suited to every person, so don't force a connection. If it happens though, awesome! A good therapist may ask you questions that make you squirm, but they will also be sympathetic and they will generally leave you with some food for thought.