Oh, yeah. With my first high school girlfriend. We were 15 and making out on my parents' couch. I took a risk and undid my jeans. It was light out. I distinctly remember pulling up the waistband of my white briefs. I also distinctly remember her looking down, seeing my hard cock in my underwear and in the daylight, and cupping my naked erection in her palm. Without question my cock was the first she had ever seen and touched. And the experience was new for me too.
It shocked me that she took the invitation – she was a “good Catholic girl.” I wasn't ready for it. I felt I was going to cum, and I did not want to scare her by making her hand messy, so I pulled her hand away. Then I let my waistband fall and came in my underwear without touching my cock.
I have many regrets because in hindsight I should've let her jerk me off. We dated for another year, and she routinely rubbed her hand on my hard cock but through my clothes. This included at junior prom, when we groped each other under a blanket. I came that night too, but with her hand on top of my jeans. (I'm pretty sure I had changed out of my tux by then.)
Why we kept things outside the clothes, I have no idea.
Things got weird our senior year of high school when she started dating my best friend. Thing was … I had the hots for him too, he was so cute! (I identify as bisexual.) Wow, the number of fantasies I had about my former girlfriend exploring my best-friend's hard cock … still turns me on, particularly the idea that her hand almost certainly has touched both of our cocks.
Many years later, I had dessert and coffee with her and current husband (not the high school friend but also very cute). I recall looking at her hands very closely. 😃