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I assume you are not circumcised. Many men have a similar problem. The fix is usually a little nick with a scalpel to loosen your foreskin and allow your glans to pass through when you are erect. As you are maturing, there seems to be some growth of your penis and lgans but not your foreskin.
When the foreskin is so tight, cleansing the area is difficult. It is most likely that some accumulation of semen, sweat, urine, vaginal lubrication and whatever. This mix is causing irritation. I recommend you see your doctor. Many doctors will fix this in the office; other will refer you to a urologist. It will be worthwhile in the long term.
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Brandye
Don't wear cheap bras!
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