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Can you tell me if he is licking at something specifically ? Or just crying and licking at his mouth or at nothing?
Can you look in his mouth and tell me if he has dental disease? That can serve as a source of pain
In a 16 year old pup I would also start to be concerned for cognitive dysfunction (canine senility). They can start to not be aware of things like they once were and it can make them anxious and cause them to vocalize.