I have had a catheter a few times, both in play and for real. For me, has never been a pleasurable experience.
The first time I was in hard labor and not progressing. The nurse/bitch (I can say that, as I am both), tried passing the cath during a contraction, which in her defence, I was having them almost constantly. She couldn't get it in, so they placed it once I was numb.
During the second pregnancy, I made sure at my very FIRST office visit that the doc agreed, and put in writing that during my second c-section the cath wouldn't be placed until after I was completely numb. And he honored that. Those were the only two real times a cath had been placed.
During play, 2 play docs have tried and failed. Not their fault. It's too painful, I tense up which makes it worse.
So for me, a catheter placement is painful. But, again, that's just me. lol