NAA in .32naa. Gave me a bright red hand. I like shooting my 44mag with full power loads better.
I had the same experience with a Kel-Tec P3-AT (.380). Gawd awful unpleasant for me to shoot; I prefer 240 grain .44 Mag out of my 5.5" Redhawk. The gun is so tiny that I really couldn't get a good grip on it, I always felt like it was going to fly out of my hand and bean me between the eyes. Couldn't hit crap with it either.
Another was my dad's 20" 12 gauge coach gun with it's rock hard plastic butt plate. Aka, the "meat tenderizer"
. After 6 shells or so I switched to shooting from the hip, which proved to be just as accurate and far less painful.
Pleasant surprises:
My S&W 642, even with .38 +P. Sure, the recoil is stout, but not near as bad as I had built it up in my mind to be.
Ruger Redhawk 5.5" 44 Mag. Recoil is certainly heavy, but it isn't painful. Also not nearly as bad as I thought it would be.
Finnish M39 Service Rifle, 7.62 x 54r. I always hear about how brutal the recoil is in Mosins and their derivatives, but I find this gun to be relatively pleasant to shoot. Granted, the carbines are probably a different story!