How do you pump as a beginner?

I just got myself an air pump and I don’t think I know how to use it. It has a sleeve (is that what you call the rubber thing with the hole?) and it is too tight for me, my penis got stuck the first time I tried pumping in level 1. Without the sleeve, I have to hold my testicles because the pump tries to suck one of them in—which happened right now and it hurt a little, I stopped the pump asap.

I am only using the pump for now, I will also start hanging but I have no idea how to do it as an uncircumcised. Do you guys have any tips for that too?

EDIT: Also, I don’t know if I am the only one who has this problem but I haven’t seen anyone else talk about it: is it possible the pumping can tear up the bridle? It feels like a pinch and I am afraid to higher the intensity and cause myself a torn bridle. Any suggestions?

Thank you!