My first time was in college, with the woman who is now my wife! The first time we fooled around was shortly after we met, we were back in my apartment and she offered me a blowjob which I happily accepted. While it felt really good at first, I started feeling some pain after a few minutes. Turns out that, through a combination of my foreskin not being able to fully stretch around my head at the time, and it being her first time around a penis with a foreskin, mine had torn just a little bit. While it was nothing severe medically, it was definitely enough to keep me from cumming. I offered to go down on her, but that was the end of that hookup.

Our first time having PiV sex was about a month later, my roommates and I put on a little thanksgiving dinner that I had invited her to. We were planning on going to a show on campus after dinner, and so I walked with her back to her apartment for her to grab something before we went to the show. We got to her room, and she just looked at me and said “want to have sex?”. Of course the answer was a resounding yes. It was definitely a little awkward to figure out positioning but we settled into missionary, and I just told her I’ll take it slow and she could tell me if she wanted a change in speed or anything. After a few minutes she said that it was getting uncomfortable so we called it there with neither of us finishing, but both of us excited to keep practicing at a later time.