There are 4 handguns I would hesitate to shoot again- as 3 were 'nasty' and the 4th was just unpleasant. In addition, I find .40S&W borderline nasty as well on light pistols.
#1 was my grandmothers Walther PPk/s- in .380. Very unpleasant, with a heavier trigger than needed.
I was around 40 when I fired it, so it wasn't due to my youth- just unpleasant. At the time, I owned a Kahr K9, and that, with +P ammo, was much more pleasant to fire, even if the ammo was close to 390 ft/lbs of energy, vs the 200 ft/lbs of the Walther.
I've read here about recoil-operated .380s and nasty. I have to say there is something there- esp when paired with light weight.
#2 for nasty for me was a Ruger LCP in .380. What was I thinking?
That said, I have shot .380s that are not nasty- but most were also heavy, and two of the top three were delayed recoil actions- not blowback [Star Model S Super and CZ24. Third was a Husqvarna 1907 in .380- 5" barrel on pistol designed for 9x20mm/Browning Long ammo, which is normally around 300 ft/lbs, vs the 200 ft/lbs of .380acp]
.
#3 for nasty for me was a Ruger LCR .38Special +P firing 125gr +P ammo. It was almost as bad as #4 for me.
BTW, this LCR was the 1.88" barrel version. I tried the same box of ammo in the LCR .357Mag 1.88" barrel and it was no worse than a Firestorm .380/Bersa Thunder, which I think is ok. The .357mag version of LCR has a heavier frame.
#4 was unpleasant, but not enough to stop before cylinder was empty. .454Casul, from a Freedom Arms revolver.
Shooting 5 rounds of this left my hand feeling like it did after firing 50 rounds of .44mag from a 7.5" Super Redhawk. However, it was accurate- 5 rounds in an almost cloverleaf pattern at 10 yards. They holes barely touched, but they touched- yet there wasn't much overlap. Great potential- for someone else.
I decided a .44mag is my upper limit for comfort- even shooting the 1200ft/lb rounds is better than the .454Casul to me.
Now, all of that said, of 9mm/.357mag/.40S&W/.44mag/.45acp/.45LC +P, the one I like the least is the recoil on the .40S&W. It is the 'worst of both worlds' compared to 9 and .45: sharper/snappier than .45, and more torque/push than 9. I respect the round, but don't see buying one in my future.