Pumping question

So I just got a pump yesterday, I think I understand how to use it. I got it at an adult toy store for like 30-something $. It comes with 3 size cups.

How is the cup supposed to sit over the little guy? Like is it just supposed to hold the head or should it go around the base?

How many times are you supposed to pump it? I tried and I can only do it twice before it’s too much and I need to release the suction.

Do you hold it for awhile before taking it off? What’s the routine supposed to be