Mine had to be a woman riding me reverse cowgirl, but she got really into it and I wasn't feeling it.
I don't know why I didn't think to say anything, but I didn't. Instead, I tried to get up (??) and as I tried to get up, I felt my dick bend.
LUCKILY nothing happened nor were there any serious injuries. But a genuine panic attack there. She felt it too and luckily we both had a time-out (as well as me being scolded for not communicating properly, which tbh 100% fair!)
I got circumcised in high school due to phimosis. I thought I had waited long enough and my then girlfriend and I tried having sex. Ripped a couple stitches and bled everywhere. Immense pain. I thought all the stitches had dissolved away already. Would not recommend. 0/10 even with rice.
I lost my virginity in the back seat of a moving vehicle while two friends turned up the radio and pretended to have a conversation like nothing was happening. It was so awkward that I didn't orgasm. Imagine what it takes for a teenage boy not to orgasm. That's my infamous first time.
Having one last fuck "for old times sake" after deciding to break off a relationship that was long dead. Both of us realizing mid-way that while our bodies were having sex, we both felt nothing. Super weird, sad, almost out of body experience. 0/10 will not try again.