Penny Barber has been "helping" her shy little friend, Sam, create an online dating profile so he can get a girlfriend. After a day of shopping to improve his wardrobe Penny insists she needs to take some pictures of him in his new clothes to put on his dating profile. Starting with modeling the skimpy underwear she made him buy! Penny does not take "No" for an answer and soon Sam is standing in front of her in tiny briefs trying to hide his little bulge with his hands. Penny takes pictures like she promised but she also gropes and teases him until he gets an embarrassing tent in his new un...

Penny Barber has been "helping" her shy little friend, Sam, create an online dating profile so he can get a girlfriend. After a day of shopping to improve his wardrobe Penny insists she needs to take some pictures of him in his new clothes to put on his dating profile. Starting with modeling the skimpy underwear she made him buy! Penny does not take "No" for an answer and soon Sam is standing in front of her in tiny briefs trying to hide his little bulge with his hands. Penny takes pictures like she promised but she also gropes and teases him until he gets an embarrassing tent in his new undies. Penny does not hesitate to reach into his briefs and pull out his little stiffy for further inspection. Just when Sam thinks it could not be a more humiliating day, Penny starts lecturing him for not telling her sooner that he had a small dick because it was going to make her job finding him dates much harder. She explains that with a cock like his he had better have other skills... right before she his head under her skirt!