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I've always wet myself to some degree when having an orgasm and I've been masturbating since I was really young. The hornier I am the more comes out. When I was younger, I instinctively would attempt to hold back that pressure, "urge to pee" feeling until I realized how much better the orgasm is when you just let yourself go completely.
It wasn't until I got better at it and was able to work myself up more, that I actually felt a "squirt" instead of just a trickle. I was probably around 12 or 13. I do remember it actually making a sound when it happened, lol, and wetting my bed sheets way more than usual that first time. I was super embarrassed and a little scared. I actually felt really self-conscious...like is this going to happen when I eventually have sex?, etc... I remember my mom thanking me for proactively washing my bedding on my own, lol.
As a teen, I used to consider it sort of a bad thing and even kind of a curse until I got older and realized how many want to do it and can't...and for me most of the time I can't help doing it. Now I consider myself really lucky. It took a few years for me to stop trying to hold it back and start accepting it and making it part of my routine.