It honestly sounds like you’ve got deeper issues with your boss. I would just shop for another job.
I’m quite introverted and have learned to only respond to questions when asked. I have no issue sharing any information. However, I have a major issue with understanding the scope of information worth sharing and when to stop. I do not let myself feel awkward in silence or the need to carry any conversation. If a person piques my curiosity, I can talk with them for days. I can find something curious to talk about with almost anyone. People that lack depth become a repetitive conversation that I will avoid.
Personally, I don’t like to be actively manipulative with people. It goes against my nature. However, if someone annoyed me like this, and I had no other outlet. I would subtly use their psychology against them about like how a psychiatrist turns a conversation to introspection and analysis. Once a person is made vulnerable through unexpected introspection they are easily dominated. I can get away with a lot of things like this because I am a big dude where people expect me to be assertive and dominant in many ways that I really am not. Your results may vary.
I had a DARE tee from school that I never wore. That was about as far as I got. At home… wearing a dare tee… once.
Sex… never discussed. Ingress path unknown. From the periphery of what I picked up from kids at school and music it sounded like confusing nonsense to me with chocolate starfish, cherries, flowers, and cat memes