Penny likes to hire the cute neighbor boy to do odd jobs so she can ogle and tease him. The little guy usually just blushes but when Penny asks her special helper to try on some underwear, he politely declines. Or at least he tries! Penny is going to get a peek at his goodies even if she has to bully him into submission with wedgies! His refusal just leads to the undies he is currently wearing being yanked out of his pants for closer inspection by the determined MILF. He agrees to try on the underwear (even though one is obviously a pair of her panties and the other are tiny houseboy briefs) to spare further torment to his butt and dignity. If the humiliation of letting himself be stripped by his hot neighbor was not bad enough, as soon as his pants come down, Penny also notices he has a boner! She makes fun of him for getting a stiffy but teases his cock to make sure it stays that way. Even after submitting to all this cock teasing and embarrassment, Penny still gives him more wedgies after she puts him in the new undies!