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Description:Out of all the items on the sexual menu, anal gets arguably the worst rap , an undeserved stigma that likely comes from a widespread lack of knowledge about butt stuff. According to Alicia Sinclair—a certified sex educator and founder of b-Vibe , a sex toy company dedicated to anal play—one common explanation for squeamishness is a lack of preparedness. When people start experimenting with sex, they typically confine touching to their genitalia. This leaves out an orifice that, for many, turns out to be pretty pleasurable. Vaginal sex tends to feel better when people play around with their own bodies before enlisting a partner, building up to penetration. How to have anal sex: