What a cool idea, Kacey! Will you tell him new things, things he doesn't know yet? I think this will definitely make for an interesting session -- glad your T agreed to it.
If I were you, I might ask questions that would be hard to ask if I were myself. Like tree asked her T in the beginning -- SO many questions about boundaries that helped her feel safe -- those questions would be too hard for me to ask if I were myself, but maybe if I was pretending to be someone else I would ask those kinds of questions.