I don't have many details on this story which is one reason I am having a hard time finding it. It was a story about a teen male babysitter that takes care of a young kid that still wears diaper. The mom of the kid still in diaper is having a hard time convincing her kid to wear his diaper and saids that some older boys still wear diapers too. The babysitter agreed and to prove the mother of the kid in diapers begins diapering the babysitter. He wets it and she jokes about how he may really need them. The babysitter tries to but his pants back on over the diaper but since it so big his pants won't fit which leads the mom to offer him a dress to wear.
The mother had dresses in two sizes in her closet one for her size and one in a much smaller size
I believe the babysitter name might have been Bobby
The family and the babysitter dressed as a girl went on a trip
