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Safe anal sex is more than just getting lubed up and ready to go. It tends to take at least some planning and requires being comfortable enough. How Risky Is Anal Sex? A Gynecologist Explains. Plus the one precaution you should always take. By Jessica Migala. Updated February Like most sexual activities, anal sex carries the risk of passing on sexually transmitted infections (STIs). Getting pregnant through anal sex is unlikely. In theory, it's possible that it could happen if semen from the anus gets into the vagina. With anal sex, sexually.