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The engaged couple sat together poolside with Aniston sporting a red bikini. And as more people began experimenting with anal sex—as anal went mainstream over the last two decades—people realized that the anal sphincter is a muscle and the secret to successful anal intercourse is learning to relax that muscle. Trending Stories. You want to be able to tell when something feels off or painful, so avoid numbing lube. The bottom line: We have not found sufficient studies to issue a reliable recommendation on what an overall safe time frame might be.