Top Definition
During the month of May, a legendary contest is held among men across the globe. You must jerk off once on day 1, twice on day 2, three times on day 3 and so on up until May 31st. You try to make it as far as you can into the month without giving up.
Dude today is day 20 of May Madness and I feel like my dick is gonna fall off.
by maymadnessguy April 22, 2009

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