Yes, once, several years ago. I wasn't even into serious pumping (never was) but I tried it just for the fun.
It was with a girl we had a "two night stand", I pumped the second day.
I will always remember her expression, she wasn't in pain or anything, she just said a moaning "oh damn" biting her lip while I was inside.
Back then though I thought it was size that mattered, I was younger and too focused on myself to try to let her orgasm.
While I do remember the night and the expression, a cock ring will have better effects and adds that veiny look instead of the fluffy softness which is a bit strange.