What is the LEAST fun gun you ever fired, one that hurt you

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Shooting Brenneke Black Magic 3” slugs thru my EAA Churchill 18 1/2 barrel pump, gun only weighs 5-6 lbs, shot 4 thru it just to see accuracy and functionality, told my wife the next time I have to shoot these rounds it will be at a charging bear, I have never been recoil sensitive, but these things hurt! I am convinced they will kill anything on this planet.
 
.50 Hawken muzzy loader. The copper cap exploded and showered my forehead with tiny hot copper peices and the stuff that makes it go boom. Felt like a blow torch. Still have a bunch of little tiny scars.
 
Shooting Brenneke Black Magic 3” slugs thru my EAA Churchill 18 1/2 barrel pump, gun only weighs 5-6 lbs, shot 4 thru it just to see accuracy and functionality, told my wife the next time I have to shoot these rounds it will be at a charging bear, I have never been recoil sensitive, but these things hurt! I am convinced they will kill anything on this planet.
I understand. Next time I shoot my elephant gun, there is going to be an elephant charging or I ain't shooting.
 
There's been a few.
The Martini-Henry carbine with full rifle loads. The only rifle that recoiled so bad that I fired another round just to make sure that I didn't hallucinate how bad it was.

One of the old man's friends with a 460 Weatherby. That infernal thing rocked my teenage world.

A FEG ppk wannabe in 9mm Makarov. One shot and done. That hurt something fierce.
 
For handguns, one of those miserable little Radom P-64s. Most punishing recoil impulse of any handgun I've ever fired, and I say that as someone who loves shooting big-bore revolvers ranging from .41 Mag. to .454 Casull.
 
I was 15 or so and my dad gave me a savage 110 in 270. It was my first scoped rifle. I underestimated the recoil and bopped myself in the eye. I can’t recall any other gun bothering me when I shoot it. Only let the 270 smack me once.
 
3. The storied PPK slide bite.:cuss:

My Hungarian FEG PA-63 in 9x18 will bite you just like the PPK. I got bit once or twice by my PA-63.

Worse experience with a shotgun was being young and dumb and shooting both barrels of a 12 gauge SxS at the same time. I was only about 10 at the time.

The most unpleasant revolver I shot was the S&W 500. One shot was enough for me.
 
I have an arthritic lump on the knuckle of my RH trigger finger from shooting both barrels of my 16 ga. SxS repeatedly, I was about 20 at the time, thought it was cool. The recoil didn't bother me much, I didn't even notice the rap on the knuckle that much, but later on in life, it has bothered me some.
 
454 Casull , hurts my hands and ears and I was still young (62).

My 416 Rigby was OK until I turned 75. I am now 79.
 
I rented a Smith 629 and shot 20 rounds of .44Mag out of it...just to see what it was like. That was the least fun gun I've shot, but I'm also a skinny wimp.
 
My Glock 43 caused so much pain in my trigger finger I couldn't shoot more than a box at a time for practice so I sold it.
 
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