For me it happened maybe once or twice so far and I've been doing somesort of an PE routine for few years now.
As Sinthious said, not everyone gets those pops. My body on another hand pops a lot, elbows, neck, knees, ankles ... I haven't experienced pain related to the pops and I didn't experience pain when I got my "penis pop."
Thankfully I had read about the ligament pop related to the penis on this forum so it didn't scare me, just a funny thing. I wouldn't wait for the pop to happen, it is to come if it is to come, usually related to a bit harder exercises; I think I was clamping when it happened the first time.