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Hi. My name is***** I'm sorry to hear about this situation with Teddi. When I have a cat at my clinic with a similar history, my concerns go toward dental disease or an oral lesion. Could he have some really altered dental pathology due to an infection that has weakened a tooth and it is trying to fall out and is bleeding? Could there be a mass that has been growing in his mouth that has ulcerated? Some can have progressed oral ulcers due to kidneys not working well too. Honestly, the best thing I can recommend is to get him to your vet so they can do a very good oral exam to see what the next step is. Could this just require a short course of antibiotics for an infection or is something more needed?