Did my dentist grind down too much of the tooth?

I had to have new fillings put in my backmost upper teeth in December. It went smoothly. However, over the holidays, I noticed that when I chewed solid food, there was an unpleasant pressure on the second-to-last molars. It was apparently really just a touch, and it was too high, especially with the filling on the left.

I went back to the dentist about a week ago. He had already told me after the occlusion paper that he couldn't grind down too much, since it actually looked fine. First, he ground down a cusp on the left, and he asked me if it would fit. I wasn't sure, as I had trouble judging it due to the slight overhang. Then he ground down the right, and I left it at that because it felt better.

After two days or so, I started to feel like my bite had changed. It seems somehow "deeper." I mean, chewing certain foods gives me a slight headache. Or am I just imagining it? I doubt that my dentist, against his better judgment, ground away a "supporting element" of my teeth. Or should I perhaps wait until I get used to it? The pain in my teeth when chewing is gone.

I don't really want to go to the dentist again because it would be a bit embarrassing. After all, it was my indecisiveness that caused it. And I can imagine he's a little annoyed that I come so often. What can he do about it? My teeth are healthy, and you can't just build up a cusp like that.

I look forward to your answers. Thank you in advance.