This, except with the addition of pitocin and the baby was not stuck. The nurse did not realize I was in transition and said it would be 12-18 hours longer until delivery as it was my first. I distinctly remember saying that no human could endure that particular pain for 12 hours. My son was born within an hour of her statement.
I had something called a torsion. Somehow, some way, some of my blood vessels got tangled in my scrotum and one of my balls was strangled to death over … days and days.
I’ve met a few women who were pretty good at that.
Broke my ankle while skydiving. That alone wasn’t painful at all surprisingly. Got to the hospital and the doc tried to get a pulse in my toes and got nothing so he told me they were afraid an artery was blocked and they needed to do a field set (?) immediately. So without any pain meds I watched him flop around my foot to set my bone. Yikes! On the plus side it worked and a surgery later it was set,
When I was in junior high school, on two separate occasions, I sat through minor fillings without anesthetic. By my own choice. This was late 1970s, and my dentist was one of those really old-school dentists who thought he needed to administer seven shots of Novocaine for a single filling*. I’d finally gotten fed up with feeling like my face was sliding off my skull every time I had work done and told him to just drill and I’d grin and bear it.
*In hindsight, I suspect the problem was that he hadn’t adequately kept up with the improvements that had been made to the anesthetics since he graduated from dental school. So he was dosing as if he was still shooting stuff from 1959 (or whenever - he was at least a decade older than my parents, probably more. When we moved to a new city and got a new, much younger dentist, I went in for a filling and he gave me just a single shot, and I never felt a thing.
The most memorable pain I’ve ever experienced was lifting my leg to clear some junk on the floor, and catching the underside of my kneecap on the sharp corner of my desk. The pain was so intense and immediate that i almost threw up, and all I could do was curl in a ball and hold my leg until it passed.
Compared to that, getting my chest opened for heart surgery was a piece of cake.
Not so much painful but extremely uncomfortable was the first time I got Lazik where they cut open your cornea.
When I was eight I had to have a baby tooth removed after I lost a filling chewing some bubble gum. Rather than replace the filling, they just decided to have it pulled. The dentist didn’t give me enough novocaine and it hurt like hell. Then she yelled at me for crying. (Hello, I was EIGHT, bitch!)
I was carrying a hundred pound concrete pylon when my feet slipped in mud and I came down with it on my chest. I swear I felt my chest bone meet my spine. A jolt of fear that someone would find me dead of Wyle E. Coyote stupidity made me fling it off of me which tore muscles in my chest. That night I hurt so bad I broke out in a cold sweat and consented to going to the E.R…
I can’t think of anything near what you guys are coming up with.
Best I can do is the time I was running up an old wooden staircase and slammed my bare shin into one of the steps. I think it was the only time I’ve ever seen stars from pain.
Nothing I did but regular attacks of acute angle-closure glaucoma had me wishing I could dig a spoon into my eye socket and pop my eye out to alleviate the pain. It was like the worst possible toothache pain you can imagine…in your eye. 
I got my wife pregnant. Labor looks like it’s really a bitch.
Hey, you didn’t say what was the most painful thing you did to yourself.
Unmedicated labour. No, I thought it was that, until I had induced labour the next time without an epidural.
My kidney stones rate pretty highly, but that’s not really something I did; that would have to be rubbing my eye after cutting chillies.
When I was a kid, I let my dog out on his retractable leash. A neighborhood dog came running into our yard and our dog freaked out. I kept trying to pull him in, but the leash was retracted all the way. I started wrapping it around my left hand over and over to pull him in. It worked until he got a burst of strength and mangled my hand. I had rope burn on half of my hand and even pieces of skin hanging off.
I was also in a car accident as a teenager. We hydroplaned and landed upside down in a ditch that was filled four foot with rain water. My elbow went through the passengers side window. I had to get three sets of stitches to close it up.
Dental pain, even with anesthesia. When I broke my ankle and managed to hobble over to an emergency room a couple blocks away (didn’t know it was broken until they x-rayed it) the doctor asked if I had an especially high pain tolerance and I answered, “My dentist doesn’t think so”.
Many years ago, I was working on an outdoor job and had to bend a piece of 1-1/4" rigid steel conduit. This requires a bender called a “hickey” and some brute strength. Basically, you put the bender on the pipe, then sort of throw one leg up and sort of fall back, letting your weight do the work of starting the bend.
It didn’t register on me that the grass was wet, which meant the pipe was wet and slippery, and when I threw my weight into it, the hickey (and the pipe) slipped and down I went with full weight onto the pipe and on my tailbone. Let me tell ya, friends and neighbors, it was like taking a 5,000 volt jolt to my central nervous system. I was literally paralyzed with the shock and just lay there while my cohorts did the “nyuk, nyuk, looka dat” routine. It was excruciatingly painful.
Bonus points: it’s the gift that keeps giving for the rest of your life. To this day, I can’t spend more than about 15 minutes in one of those typical conference chairs you find at every event, and even a long movie can be an ordeal.
Tried hooking up with a really butch girl by pulling my pecker out and putting it in her hand.
555 How was that* painful*?
That I did to myself: Fracture my humerus doing acrobatics. Combination of being a beginner to the move and being flexible the wrong way. My supervisor saw the fracture x-ray (it is very pretty) and commented “lots of torque”. Ayup…