Sounds like a combination of you just getting unlucky and having very low pain tolerance. Personally I don't mind it hurting a bit sometimes, for smaller stuff

Sounds like a combination of you just getting unlucky and having very low pain tolerance. Personally I don't mind it hurting a bit sometimes, for smaller stuff I usually even opt out of the local anesthetics because I don't like running around with a mouth that feels like it's full of cotton. Those are medical procedures after all, they are not supposed to make you feel amazing (at least during the process) they are supposed to "fix you", as such the process can be quite uncomfortable like many other medical procedures. If pain is your issue you should try looking for dentists offering less-conventional methods, like hypnosis or electric anesthesia. But I doubt there's anything anybody could ever do to make a visit to the dentist "comfortable" for you, short of full anesthesia so you don't even notice what's happening. I guess I got lucky because I don't really mind, never did. As kid I would hate going to the haircutter, but I loved visiting the dentist because of all the cool tools he had. Being weird sometimes has its advantages ;)