Based on the character from classic American literature, it is the act of tricking someone into doing things they would normally never do voluntarily, all the while having them believe they are the one getting over on you.
Dude, after I Tom-Sawyer'd the prude she was begging me give her the Glass Bottom Boat treatment.
by JVanG April 20, 2005
When you start giving yourself a handjob (white washin') and then trick a bitch into finishing the job...
The Tom Sawyer, is when you text a girl to come over and you start masturbating before she comes, you talk her into finsihing you off and cuming.
by DCadvantages March 20, 2008
Right before a man reaches his climax he then rubs it on a females leg, Cumming while doing so, rubbing the semen into her thigh like white paint on a fence.
"Dude, I just tom sawyer'd the shit out of this girl."
"You can definitly tell I painted her fence white."
"My dick is a paint brush!"
"Painted that bitch like the sistine chapel."
by MegaDongPeak August 19, 2014

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