So I am a pansexual transgender Male and I have a boyfriend (who is Male and also pan.) We are also a switch couple. We are pretty sexually active, but he wants to try something. He wants to be the bottom. We have tried it before just a little bit and he didn't seem to be able to take it well. Is there any advice that you guys could give me? He says he really will enjoy it even if its painfull, but I want to make sure that I don't hurt him and that he actually gets pleasure out of it.