Contestant #4: Robert the Retard Cross Dresser

June 10, 2010
Photo: The Howard Stern Show

The fourth contestant, Robert, was a cross-dresser who hoped to use today’s prize money to pay for a sex change operation: “I used to dress up in women’s dresses and my mom said I was a lot prettier than my sisters…my mom wanted me to be a girl and I just want to follow my mom’s wishes.”

Robert also reported that he was legally retarded and on both SSI and SSA support checks from the government.

Robert said he was into women, but never had sex with them: “I’ve had girls all day and all night.” Robert admitted that he only used his penis for pleasure in private.

Howard asked: “Would you say you’re confused sexually?” Robert nodded: “A little bit.” While Robert denied ever having sex with a real woman, he did confess to trying to f’ a blow up doll: “One time. My father bought two of ’em. She blew up in my bed…I took the pump and pumped her up too far and she blew up.”