Liz Buchanan BVSc MRCVS
Keymaster
Hello - I think that this would be very sore left until Monday and am not going to suggest that you squeeze an anal gland. Your dog appears to need an examination and appropriate pain releif as licking can cause extensive damage, so it sounds to be very worth chatting through the available options with your vets' out of hours team, who are licensed to advise you.
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