After I've jerked off (or sometimes even just had an erection), often my short foreskin will bunch in a slightly different way than if I'd just pulled it back. It's as if moving the shaft skin back and forth when hard makes the very tip of the foreskin get wedged right behind the glans. As this part of the skin must move first in order for my foreskin to roll back, when it's stuck behind the head it neatly holds the rest of the skin behind the head very firmly
Any guys have a similar experience?
I understand completely. It happens to me too but generally not for long because I have a pretty loose foreskin (and a short one too!) and the rest of the skin finishes up by moving forward and pulling the shaft skin with it. But it can take 10 minutes or so to eventually move forward perhaps a bit more, but it eventually comes back to neutral so to speak.