Definitely see a doctor pronto! This is serious, and it's not worth risking hearing loss. He may have to take some time off from swimming or keep his head above water and just do vertical kicking or water jogging while it heals.
As far as swimmer's ear, this is something I'm very familiar with. Sadly I get it several times a year.
I have not found ear plugs to be effective, but they do have headbands now that are supposed to keep water out of the war. I haven't tried these.
You can use a couple of drops of baby oil before swimming. I have read that this helps prevent the water from staying in the ear canal. Just get a medicine dropper and a small container for the oil.
Afterwards, I use a mix of 1/2 vinegar and 1/2 peroxide to try to prevent ear infections. Remix this every week because I have heard that perioxide doesn't keep long. Use only 2-3 drops in each ear and DO NOT DO THIS while you have an ear infection or you'll be screaming in absolute agony for hours.



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