Back from the break, Howard introduced the judges for "The Office" contest. The first was a pre-op transsexual named Danna and the other was Big John from Scores. Howard had Danna stand up so he could get a good look at "her" and said "she" was looking better than ever, in fact he could hardly believe "she" had a penis. Danna recently got breast implants but refused to show them unless Howard helped with "her" "cranial feminization." In other words, "she" wants "her" skull and chin bones shaved down to make her look more feminine and that only costs $42,000. Big John said that he was still trying to get over the fact that "she" was really a he. He said that if "she" would become a post-op transsexual he would go for her. John was really smitten by Danna. The sparks were flying. John said that he's been with a 1000 women in his life and he was really thinking about going out with Danna. Artie wanted to know if he really wanted those 1000 women to be erased by one man! Gary asked Danna when she breaks the news to a guy that she's a he. Danna said that "she" recently met a guy in Egypt who asked "her" to marry him before he found out that he was a "she." When he finally did find out, he never called back. Danna then got back to seducing John. "She" said that he needed to be treated like a king, and "she" was just the person to do that for him. Danna said "she" loves to clean a man's house, to which Artie replied "You do clean a man's house, YOURS!" John told Artie not to talk to his "woman" that way and Danna said that not only was John beautiful on the outside but he was also beautiful on the inside. Then John did a shot of tequila. Danna started to tell a story about being flown out to LA by CBS to tryout for "The Amazing Race" and being sequestered in a hotel full of pilots. John asked if she had cheated on him, but she said she hadn't and John was happy he didn't have to punch out a Delta pilot.
Enough of the love story. Howard invited the contestants into the studio one by one and John and Danna gave their scores. The first contestant was Dan/Daniella. Dan said it took most of the day yesterday to get ready, including shaving off his beard. Danna thought that Daniella was a 10, at least until he lifted his dress, then she changed her score to 4. Big John had not had enough to drink yet so he gave Daniella a 0! The second contestant was Will/Willamena. Willamena was wearing a nice mini-skirt and the guys in the studio seemed very impressed. Will said he spent a few hours getting ready yesterday (also shaving his beard) and had a transvestite makeup artist do his hair and makeup for him this morning. Howard said he looked like a psychotic Joan Cusack. Artie said that, for once, he was speechless and Gary thought it was disturbing to see a guy he's talked football with dressed this way. Will even turned around and hiked up his skirt to show off his thong! Danna thought Will looked great and gave him an 8 and John gave her a 6. The third contestant was Jason/Sloan. Howard said he looked a little overweight and Big John thought Sloan looked like Ricki Lake. Jason said he spent most of the day getting ready for this and even had someone give him lessons on how to walk like a girl, which he then proceeded to demonstrate. Danna thought he needed sexier clothes and gave him a 5 and John gave him a 2. The fourth contestant was Sal the Stockbroker who tripped and fell on the way in to the studio and never got to give his girl name. It seems that Sal has trouble walking in heels, but said in his best fem voice that he was ok. Before Danna could give her score, Sal pulled down his panties to show his (apparent) lack of a package. Danna gave him a 1 and Big John gave a 7. The fifth contestant was Isaac (also one without a girl name). Isaac quickly flashed his ass and said that he hadn't gotten any sleep as he was up all night getting ready. He said he got a lot of help getting ready and even shaved his ass. Gary thought he missed a few spots though. Danna thought he looked great and gave him a 7 but John only gave him a 1. The sixth contestant was Richard Christy. When Richard walked in Big John tried to quit! Richard also spent a lot of time getting ready for the competition, including the aforementioned body shave in the bathtub. Danna gave Richard a 6 and John gave him a 2. Richard then offered to make out with either of the judges for a better score, but there were no takers. The seventh contestant was Benjy/BenShe. Gary said he looked like Monica Lewinsky. Benjy was deep into his schtick coma and was flirting with Howard. He even managed to get in a few plugs for the makeup and clothes he was wearing. Danna liked BenShe's clothes and gave him a 7 and Big John gave him a 3. And the winner was?Will/Willamena. Gary gave Will his check for $5000 courtesy of "The Office" (which airs tonight on NBC after the "Apprentice"). BenShe ran out of the studio crying and Sal got pissed, saying that he got all dressed up, shaved his goatee and burned his nipples with hair removal cream for nothing.