Masturbation was a tough topic--I reflexively said something that made him feel awful. He said that my response made him feel like a dirty old man asking what color my undies were. I later told him that I was sorry, that I knew my reaction would make him back off. He has never acted creepy, but I used that fear to get off the topic in a hurry.
When he asked for clarification around childhood neglect/abuse situations, that sent my heart pounding and I thought I would pass out.
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