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I'm not an expert, but just an over educated enthusiast with a fruit salad of actual experience. I think I can explain this for you.
Resistance in an electrical circuit causes heat. Light bulb filaments are resistors, as are the coils of nichrome wire in toasters, hair dryers and cheap space heaters. The wire in the extension cord is a pretty good conductor, within limits, but it does have some resistance. The fatter the copper wire, the more amperage it can carry without noticable heating. Overload even a great conductor like gold, and it will heat up. The triggers in nuclear bombs use high voltage and very thin gold wires that instantly vaporize, setting off the chemical explosives that start the bomb.
In an extension cord, the highest points of resistance are the ends. The solid copper plugs and sockets get oxidised, creating resistance for the flow of electricity. The ends will get hot. That's how house fires begin - outlets overheat from overloading and/or high resistance connections. Hopefully, breakers pop first, but there was a problem years ago with
aluminum house wiring causing fires because the connections with non-aluminum components heated/cooled at different rates and the screws in outlets worked loose. It was especially a problem in kitchen and bath outlets because of humidity - copper and aluminum will corrode when in contact. Building codes were changed, electricians were trained on proper installation of aluminum wire and outlets were redesigned to fix the problem, but if your house was built in the 1970's I'd suggest having an electrician inspect the outlet in question.
I've overheated extension cords, and still use them. They end up twisted like a phone cord, as the copper expands and then shrinks again. The twisty part will be at one end or another, from whichever connection had the highest resistance. If the end at the wall is the highest resistance, the outlet will also get hot.
I recommend owning a point-and-click infrared thermometer. Very useful tool, for things just like this.