Anal Cowboy (Cowgirl) Share definition Flag Similar to Butt Pirate and Rump Ranger but it could go for both sex. Riley is an Anal Cowgirl Austin is an Anal Cowboy (Cowgirl) Anal Cowboy (Cowgirl) by AustinJP August 27, 2008 0 0 Get merch Get the Anal Cowboy (Cowgirl) mug. Buy Now — $32.95 See more merch