Oh gosh I would suggest maybe giving him a stool softner so he can go poop. It will also make the poop a bit softer so it doesn't further irritate the anal glands.
I never express the glands. Zoey eats hard food so her poop is solid and the vet told me when they poop it will press on it and clean it out on it's own.
Over cleaning can cause a host of problems with the anal glands. By the way if it's usually an anal gland issue you will see them scooting. So if he is constipated then that is being caused by something else.
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