As above, dropping a round into the chamber and closing the slide gives the extractor a real beating, and there's an excellent change that the extractor hook will break.
The worst gun for damaging the extractor is the 1911 with it's internal extractor that acts as it's own spring.
The real danger to the bullet itself is bullet set-back.
When a bullet hits the feed ramp the impact hammers the bullet back in the case. This causes pressures to skyrocket, and the shorter round tends to jam.
Back in the 80's when the big police move to the auto pistol began, there was a rash of second round feed stoppages.
The officer would fire his first round, and the gun would have a failure to feed jam.
It was discovered that officers were inspecting their pistol by removing the magazine, removing the round in the chamber and inspecting the gun.
To reload, the officer would chamber the next round in the magazine, and put the first round back in the magazine.
What this meant was, the same two rounds were getting chambered over and over again, and the bullets were being driven back into the case.
When the gun was actually fired, the too-short round would fail to feed.
So, always load by feeding a round through the magazine, and don't chamber a round more than about 3 times before shooting it in practice.
I keep a "gage" round handy. This is just a factory-new round that's never been chambered.
I use it to check a round for correct length before chambering it by comparing length.