cheesy chester Share definition Flag a cheesy chester is when you eat a whole bag of Cheetos, and then finger a vag. fuckin' eh. a cheesy chester is basically the fakest sex move ever invented, but is good for its comedic purposes. cheesy chester by xtrustmetwicex October 8, 2009 0 0 Get merch Get the cheesy chester mug. Buy Now — $32.95 See more merch