As tslust said..you should joke around with him and see where it goes.
Lately my friend and I have been jokng around with the subject because of the movie hang over 2. Things like, "hey would you do this chick?" what if she had a dick? would you let a tgirl bang you for 1 million dollars?" But he always refers to them as men. I think I said something like, "most tgirls look better than our obese population." The conversations never really went anywhere though. Kinda sucks but I tried.
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