Leaky Madison Share definition Flag When a man ejaculates in a woman's anus, and she then squats over his chest and allows the semen to leak out onto him. "I hate hanging around Travis. All I can think about is Meghan giving him a leaky Madison." Leaky Madison by WeirdFetishes December 11, 2009 0 0 Get merch Get the Leaky Madison mug. Buy Now — $32.95 See more merch