6. The Smoking Jacket

Complete story — includes the ending

Larry frequently visits Louis at the hospital, hoping he will die soon and donate his kidney to Richard. Nat sends Larry's cousin Andy his smoking jacket. Thinking his increasingly senile father meant to give the jacket to him, Larry negotiates for the jacket in exchange for bringing Andy on his visit to Hugh Hefner 's Playboy Mansion. He also brings along a terminally ill young boy who caught him fiddling with the wires to Louis's life support and blackmailed him. However, he fails to fulfill the boy's wish to see a naked woman because the girls at the Playboy Mansion are more prudish than Larry thought, covering up their private parts and running away screaming the instant they spot a male in the pool area. While there, Larry lets Hugh Hefner try on his smoking jacket. Hefner wears it during a long bathroom trip, so Larry swaps it with Hefner's own smoking jacket when no one is looking. While looking for another way to fulfill the terminal boy's wish, Larry accidentally walks in on Andy having sex with a Playboy model, to the boy's delight. Nat complains that his smoking jacket has been stolen, having forgotten that he mailed it to Andy. Larry gives him Hefner's, but he recognizes it is different, and demands his real jacket back. Larry calls in his favor for showing the boy a naked woman, and the boy asks the Make-A-Wish Foundation for Hefner's smoking jacket.