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How to make anal sex pain free? I gave attempted it twice and neither one if the two were successful. He might have penetrated about an inch before I moved away due to pain...

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Hi there

Unlike the vagina [which can lubricate itself] the anus is devoid of any lubrication. Generally partners who indulge in anal sex usually take an anema or a laxative to evacuate bowels [to reduce risk of infection] and then use lubrication before attempting anal sex.

However if you are suffering from piles - anal sex can be quite painful and then again piles may bleed. Hope this helps. Good luck

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