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Tight foreskin and sensitive tip
I have a tight foreskin which does go back all the way but with an erection it is difficult to get it back up.Also during the act of intercourse the tip of the penis is very sensitive so instead of pleasure it feels painful.
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You might be suffering from paraphimosis. Visit a surgeon and let him examine you for proper diagnosis and further treatment.
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Disclaimer : The content is not intended to be a substitute for professional medical advice, diagnosis, or treatment. Always seek the advice of your physician or other qualified health provider with any questions you may have regarding your medical condition. Never disregard professional medical advice or delay in seeking it because of something you have read on this website.