I'm still to this day not sure if my first experience counts, it was a mortifying 'couldn't keep an erection situation', but technically there was some penetration. Cringey to think of even now.
We were together over a year and madly in love, but I wanted to wait til I turned 17, we did lots of other intimate stuff but planned to lose our virginity together that Summer. It was hard on him, he was older and in Uni and turning down opportunities cos he had a girl back home while his friends were having one night stands, yet he was still a virgin! When I said I was ready and we arranged a meet up alone, which was really tricky at the time, we had that disastrous attempt and it was really upsetting. After that he was withdrawn, started being mean to me and we basically argued all the time. We had another chance to be alone weeks later and he had been drinking and smoking weed, and basically fell asleep as soon as I started to talk to him. So we broke up. I went off to Uni not knowing what I was, I didn't want to sleep with a stranger but didn't want another relationship. I got into a friends with benefits situation with someone who kind of knew the story, but then he told his pals and they all thought I was an easy lay. You can't bloody win.
A few months later after moving in the same circles socially and things being hostile I got to talk frankly and soberly with my ex. He finally confessed that he had been drunk on a night out and shagged a girl in the car park of a nightclub that he only met 5 minutes earlier. That was literally a day or two before I said I was ready for us to sleep together. This information broke my heart. But thinking back I see he was tortured by a guilty conscience and couldn't be intimate with me. About 10 years later when I was engaged we bumped into each other, he was really drunk and told me that he missed me for years and he had hardly let anyone truly know him the way I did, he said he couldn't let people in and I said I forgave him for what happened back then. It was nice to have closure because I felt for years like I wasn't good enough and it sounds like he was troubled by it all too. We are not in touch but he lives near my family home and I kind of know the girl he married, and I could track him down in 5 mins if I chose to. I sometimes feel sad just thinking about it all, sorry for the long post but it feels good to rethink it and type it out.