Hello, my name is Dr. Kara and I have over 20 years of experience as a veterinarian.
I'm so sorry to hear that your fellow Brago is so uncomfortable.
Possible reasons for his discomfort include a food allergy or sensitivity, constipation or diarrhea, flea allergic dermatitis, tapeworms, full or infected anal glands or impaction of the glands.
I would recommend that you check his stools for worm segments and I recommend continuing to do so. Make sure that his stools are normal size and consistency too. If he's had fleas at all in the past year then tapeworms are a real concern and then you may choose to treat for those with a wormer containing praziquantel such as Droncit or Drontal.
If he will let you touch the area he would benefit from a warm compress to the area, patting dry and then applying a light coat of cortisone cream (like cortaid) to the area a couple times a day. Try and distract him after applying the ointment so he doesn't lick it off. While it won't hurt him if he licks the cortisone cream off it won't be there to soothe the inflammation present. In some cases where we simply cannot get them to stop licking placing an Elizabethan collar (lampshade collar) is needed.
In case this is allergy related you can try:
1) Benadryl (diphenhydramine only don't use the combination products with acetaminophen or decongestants as they can be toxic) at 1mg to 2mg per pound or one 25mg capsule per 25 pounds of dog orally every 8 hours.
OR 2)Claritin (loratidine) at 5mg per 25 pound dog once or twice daily.
OR 3)Hydroxyzine at 1mg per pound orally every 8 hours.
OR 4) Chlorpheniramine at 4mg to 8mg per dog once or twice daily.
If he still seems uncomfortable with antihistamines and a warm compress/cortisone then his anal glands should be checked. Ideally this should be done by a veterinarian but an experienced groomer may be able to help too if they are simply very full and you cannot get him seen tomorrow.
If his anal glands are very full sometimes you may be able to see an obvious swelling at the 5 o'clock and 7 o'clock position around his anus. If that is the case you can try a gentle upward pressure externally with your fingers from the bottom of the swelling up towards the anus to see if you can get them to empty. This often works better after a warm compress on the area for 5 minutes or so.
Best of luck with your fellow. Please let me know if you have any further questions.