Top definition
Moving seamlessly from one hole to the next while preforming oral sex on a female.
George Washington was a master at crossing the delaware, without ever getting wet.

I tried to get him to cross the delaware, but he said he'd never leave New Jersey.
by Kim & Kate February 03, 2009
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Straddling a woman's face, balls in her mouth, while titty fucking her, one leg on the floor, the other on the bed, reminicent of the pose struck by George Washington in the famous Revolutionary War Painting "Washington Crossing the Delaware"
After an extended amount of time in a Captain Morgan style doggy position, he flipped her over and and switched into his "Crossing the Delaware" stance until his leg started to cramp.
by dogh2o December 29, 2011
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Having sex with a girlfriend or boyfriend while he or she is asleep. Originates from George Washington's sneak attack against the British on Christmas Day 1776 and his numerous nocturnal sneak attacks on Martha W.
Bill tried Crossing the Delaware last night, but I woke up and pushed him off me.
by countryturkey March 26, 2010
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