Aunt Polly punishes Tom by making him whitewash a picket fence that runs next to the sidewalk. It's a beautiful Saturday morning, and Tom longs to be out having fun, as he had planned to do on his day off from school.

Tom pretends not to notice Ben Rogers at first because he fears that Ben will make fun of him. Ben is an assertive, adventuresome boy like Tom, and Tom knows he will not be afraid to ridicule him for having to work.

As Tom expects, Ben comes up the sidewalk. He is eating an apple that Tom would love a bite of, whooping from time to time with happiness and pretending to be a steamboat. Tom knows Ben is there, but pretends not to notice him.

Ben does stop and jeer at Tom, saying that he is going:

a-swimming, I am. Don’t you wish you could? But of course you’d druther work—wouldn’t you

Tom thinks fast as he wants to save face in front of this rival boy. He says that whitewashing isn't work to him. He makes it seem like the best kind of fun, so much fun, in fact, that he's reluctant to let anyone help him. This, naturally, inspires Ben to want to help and before long he has bartered his apple for a chance to put white paint on the fence. This encourages the clever Tom to get others boys to pay him for the privilege of doing a chore.