Chubby Chester Share definition Flag A half erect penis. It's getting hard, but it's not quite there yet. "I would like to stick my penis inside of you, but unfortunately I only have a Chubby Chester at the moment." Chubby Chester by van Br00 January 19, 2013 0 0 Get merch Get the Chubby Chester mug. Buy Now — $32.95 See more merch