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The cartwheel sex position is an acrobatic, rear-entry sex position. The position gets its name because the man stands on his head, appearing as if he's about to do a cartwheel. His partner bends over in front of him, allowing him to insert his penis. A variation on this position, dubbed the backdoor cartwheel, has the penis entering the anus instead of the vagina.
To perform the cartwheel, the man stands on his head, using his hands to steady him, as if he's preparing to perform a cartwheel. It's a good idea for the man to do this with his back against a wall for extra support. His partner then stands in front of him, with their back facing his body and their feet resting on either side of their head. The receiving partner bends over so the male partner can insert his penis into the vagina, or in the case of the backdoor cartwheel, the anus. This sexual position is seen as especially challenging because it's difficult for the man to balance on his head, and maintain an erection when blood is rushing to his head. This position also relies on the receiving partner to maintain momentum and keep his penis at an angle which is comfortable for both participants.
Looking for more sex position ideas? Check out our Sex Positions Playlist.