I've had a catheter up mine when I had surgery and while it was so convenient while it was there it hurt like a bitch when they removed it. Ouch! Hate to even remember that!
Yeah ive done that too. My wife stuck one of those sounding toys down my penis and I cummed with it in deep and dude it hurt sooo bad. Never try to cum with one all the way in. My dick felt like it almost exploded. Totally ruined orgasm
Owch! Reminds me when I wore a kalies teeth device, it's a tune filled with spikes. Between the conversation I was in and the pain from the device I was dying in arousal so I played a bit. Yup I peed blood after that. I couldn't even pee it was restricted.