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Lusty Lilly Bell has had a crush on her family's older friend, Will Pounder, ever since she was old enough to start liking boys. Recently, Will has begun to reciprocate the attraction. It's clear as day that there's something up between Lilly and Will, even when they think they're being subtle. They get away with their flirtation when Lilly spies on Will getting out of the shower. Later, though, when Lilly hops onto the counter in a miniskirt and spreads her thighs so Will can see her panties, Lilly's stepmom, Ryan Keely, catches on to what they're doing.
Jimmy Michaels is shy and not particularly socially adept. He knows that he wants to go to the school dance, but he doesn't have a date and doesn't care to go alone. When his stepmom, Maggie Green, discovers that Jimmy isn't intending to go, she decides to take matters into her own hands. Busty Maggie gets Jimmy up off the couch and says that she'll measure him for a suit so he looks quite handsome. The only catch is that Jimmy has to strip down to his boxer briefs so she can measure the fit appropriately....
