I had an expierience exactly like yours at the dentists. He pulled 4 teeth like that. 15 shots in the mouth did absolutely nothing to ease the pain. I haven’t been back to a dentist since.
For some reason some people are very tough as far as getting Novocaine to work. Sadly I am one too. Last time the oral surgeon had to take out some broken teeth he could not get my jaw numb. I told him it takes a LONG time.
Finally he got pissed off (after like 18 shots) and had me come back the next day to be put to sleep. The CRNA had a tough time getting me to sleep! When I woke up the oral surgeon said it was better I went to sleep because the one tooth had an extra long root.
Another dentist had told me that in his 20 years had had only run into a few like me. He said often it is because the nerve runs deep through the jaw bone. Also some people are resistant to the effects of most of the ‘caines.
No wonder I never got numb at the dentist as a kid. Dental work was always painful. Always.