To be convinced that something that is to your benefit is actually harming you. This is similar to when Tom Sawyer convinces the neighborhood kids that his chore of whitewashing a fence is actually the most fun thing ever, to the point of getting items for letting them do his dirty work for him.
Me: I got played by this guy pretending to be a hot chick, but I convinced him that I was leading him along the whole time instead.
Friend: You totally Tom Sawyered that dumbass!
Friend: You totally Tom Sawyered that dumbass!
by IanTheGreat January 14, 2009
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The encore act of painting the Vagina walls with the man’s semen. Slide the tip to create an even coat finish on the proverbial fence with a level of quality to truly honor Tom Sawyer. Fact - it is okay to allow some paint to enter between the crack of the fence.
I pulled out and Tom Sawyerd her lips with my burgeoning load of sizzling hot semen; stroking up and down to create a fantastic work of art.
by JKleezy January 4, 2020
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