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Cat not cleaning his undercarriage
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If he's now dieting could you perhaps use food treats to get him to associate grooming with a pleasant experience. Perhaps some small pieces of chicken or something low cal so he doesn't put on too much weight. If one of you feeds the front end while the other does the grooming it might help him to relax in this situation.
I had to do this with my dog who was terrified of brushes and combs. Took a while but I am now able to brush her back legs and tail area without fuss.0
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