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I am not a doctor (yet, I'm 4th year medical student) but this sounds like a condition called phimosis. The whitish ring you describe is found primarily in balanitis xerotica obliterans, which is a common cause of phimosis.
This is definitely something that should be brought to the attention of a doctor and I'd recommend taking him to your regular family physician, and, if needed, your physician will refer you from there. Treatment options are medical and surgical depending on the severity of the phimosis and underlying infection.
I hope that helps...