Crossing the Delaware is when you and your friend/partner board an airplane sitting in seats opposite one another across the isle with powdered wigs ready to be worn. It’s important to store said wigs until you’re in takeoff to avoid suspicion. Once the your plane begins takeoff and the fasten seat belt sign is on with no flight attendants in the isle, you and your buddy start by donning your wigs. Then, jack each other off another across the isle to full completion. If you can both finish before the flight attendants resume working in the isles, you have successfully crossed the Delaware. If not, America loses the revolutionary war. Move with purpose.
by General Jameson July 19, 2019
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
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.
by countryturkey March 26, 2010
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.
I tried to get him to cross the delaware, but he said he'd never leave New Jersey.
by Kim & Kate February 4, 2009
When hitting a parter from behind, the person swings their leg up onto the neck of the receiving partner. The position should be similar to that of the president’s famous painting on that chilly December night.
by Chenny kesney May 20, 2019