I’ve been seeing this guy for four months now. We saw each other last night and it was his first time going soft during sex. He wanted to try doing anal for the first time for us and so we tried it. He just couldn’t keep it hard enough to put it in all the way. After that he was just soft and I couldn’t get him hard again for a few minutes of trying. We just took a break for maybe 10 minutes. He was able to get hard again and we just decided to do vaginal sex. ( don’t worry, yes we changed the condom out. ) I don’t know, I kind of felt off about it. Wondering if it was me he was turned off by or if he was just stressed. When we were taking a break he sounded a little upset with himself about it and I reassured him it was fine.