From the time I was first getting seriously hard, until I was about 23-24, my erections were almost always the kind where my glans would be purplish and shiny. The shaft would be not just erect, but *hard*. They rarely hurt, but the degree of ache was often quite uncomfortable.
That was usually solved by getting off, but sometimes I would have to orgasm 2-3 times before I would relax. Not a problem to me when jacking, or to my girlfriend at the time.
Thing is, it would ache if I was getting off daily, which was usually the case. But skip a day or two? Then an erection could really hurt - the kind where I could feel my heartbeat in my cock.
These days, I don’t get that kind of ache unless I edge. If I do the kind of edge where I have cool-down periods, and the precum is really flowing, the ache goes away, but I get really hair-trigger excited. Sometimes after I blow I get a internal ache feeling that is nice - it kinda feels like being horny, even after it is all over. It usually lasts about 2 hours, and I like it.
The only other time I have had an erection that was painful was when a girlfriend really teased the shit out of me after she rubber-banded me.