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Hello, JACustomer. I have been a Veterinary Nurse for over 15 years and would be happy to help you today. I'm reviewing your question right now.
1) Do you have video of him licking himself? 2) Have you noticed him dragging him back end on the carpet? 3) Frequent trips to the litter box? 4) When he licks, does he leave his legs together and come around over the top of his thigh, or does he attempt to lick between his legs?
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I am concerned that Shadow may be blocked. By that, I mean that a small amount of sludge in the bladder has passed through the urethra to the tip of his penis and is keeping him from being able to urinate. This is a medical emergency as the bladder can rupture and toxins build up in the kidneys sending him into renal failure.What I cannot tell you over the computer is whether or not this is truly an anal issue or not. A penile issues can present just like an anal issue as cats will groom all of their genitals and the area with the most pain. Most cats with anal gland issues or something to do with the anus do NOT hiss and cry out in pain. However, it is one of the most notable signs that a cat is blocked.With this, I would err on the side of caution and seek out a medical facility that can see him overnight. If one does not exist in your area, he needs to be examined no later than tomorrow morning. Waiting until Monday may have a grave result.I'll be standing by in case you have questions.
Checking in on your companion, Mr. Matthew. How is he today?