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I have had that on the same nippel with both of my kids. it is most likely a latch issue. I know it was in my case. That particualr nipple is smaller and I think they had a hard time keeping suctino on it for some reason.
I worked and worked with getting a proper latch with both of them but still had problems the eniter nursing realtionship (not blood blisters always, but often pain)
Hunter nursed until he was almost 3 and Callan is still going stong at newly 2. there wre times especially at the begiinnig that I had to grit my teeth curl my toes adn breath trough it but I did get better as Iworked to correct their latches. It didn't hurt constantly but as they got older and got lazy with latch it would crop up now and again.
The best advice I have is to make sure he is opening his mouth wide to latch on not sucking it in through is lips. (both of my kids liked to do this, ouch!) if you need to press down on his little chin with your finger to get him to open up wider. He needs to get as much areola as possible in his mouth. If you have large areolas (lke me) it will be impossible to get it *all* in ther but as much as possible.
It is possible that he may have a short frenulem (the skin that attatches the tounge to the floor of is mouth) IN retrospect HUnter had this problem. We idn't get it clipped but you might bring it up with the doc if it doesn't improve after working on his latch.
Good luck, I hope it starts to feel better soon. He is simply adorable!
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