I remember my first masturbation at 10. It was the first time I as able to retract my foreskin during erection. A friend had showed me how to j/o but I couldn't until my foreksin retracted. So on that day, I tried it.
I didn' quite know when to stop but eventually, the sensation became overwhelming and I stopped as it started to hurt a bit like when I was a young boy and touching glans was painful. (at 10, no sperm yet, so no defined end to orgasm as is the case once tyou start to ejaculate). But I think the brain gets conditioned to stop after orgasm because of early masturbation experiences.
I think one becomes conditioned to stop after the pumping action is done. After that, you go into "postplay" whene you might do some gentlty stroking or fondling. For me, after I became fully circumcised, I discovered the cicumcision line, already very sensitive, becomes VERY sensitive after orgasm and great to slide ginger around it, especially if wet with sperm.