I’m a 33-year-old woman in a relationship with a 43-year-old man. My boyfriend’s fantasy is to have a threesome with another man. He enjoys watching me have sex with other men and then intermittently fucking me. But he mostly likes to watch me get fucked. For a long time, my boyfriend would send nudes or videos of him fucking me to men we met on dating apps. We would talk dirty about it during sex. Recently, we met up with a man for the first time. I don’t think it went well.
My boyfriend and I have had conversations about my fear of contracting an STI. So before the threesome started, I explained to my boyfriend and the other guy that condoms were required. They both agreed. This guy was really nervous and when he put a condom on, he went flaccid. He would try to fuck me with his flaccid,...