riding the cotton cowboy Share definition Flag When a girl is horny and straddles their pillow and grinds on it to get herself off.. I got caught riding the cotton cowboy, so I was told to wash all the pillows now riding the cotton cowboy by JuicyTroll June 21, 2015 0 0 Get merch Get the riding the cotton cowboy mug. Buy Now — $32.95 See more merch