Howard said it was time for the Hottest Cougar contest. He wasn’t sure if he wanted to hear the intro yet. Howard said he might have to explain it first. Howard said that a Cougar is an older woman who is looking for younger men. He said they have a 40 year old, a 38 year old and a 50 year old. Fred had some cougar sound effects that he was playing whenever Howard would say cougar. The 50 year old cougar sound clip had less energy than the other two.
Howard said they have pictures of the women up on his web site so people can play along at home. He said he doesn’t care what age they are. He said he’s going to wait to see their personality and all of that before he judges.
Howard played a Baba Booey song parody to the tune of the Abba song he was singing earlier. Howard said that was from Psyche. They weren’t sure how to pronounce his name though. Howard said they’ve been getting a slew of songs lately. He said they got some Ham Hands Bill songs but his don’t make sense. He said that he wanted Gary to burn some of them because they weren’t funny. Gary said that his favorite was the Black Hole Sun parody. Howard said he hates that one. He played it for Robin. Robin laughed when she heard the first line.
Howard played another one from Ham Hands Bill where he sings about not fucking with Howard. Howard said he thought they were so bad he shouldn’t subject his audience to them. He said he’s trying to capture that first song parody he did for them that won him a contest but it’s just not working.
Howard got back to the contest and said it was time to play the intro. Fred played the intro where they talked about what this contest was about. Howard did his pageant host voice and introduced Robin and Gary. He said they were going to have Fred judging as well.
Howard said the first contestant was Karri Lewis and she’s 42 years old. Howard said she’s got a great body for a 42 year old. She has 3 kids and she’s divorced. Howard said that she has a kick ass body. He asked if she dates younger guys. Karri said that she does go for the younger guys. She said she actually does some modeling and bikini work. Howard asked if her stomach is good. She said it actually is. Howard saw it and said it was a good stomach.
Howard said he thinks that she has a shot there today. The last guy she dated was 29 years old. Howard asked if she fucked him. She just laughed. Howard asked if he gave it to her hard. She said of course he did. She said that she needs mental stimulation though so she doesn’t fall in love with these guys. Howard asked how old the kids are. She said that they’re 15, 13 and 7. She said that she has all boys too.
Howard asked why the husband left her. She said that he was an Asian man and after having the kids he said that he wanted to have kids with a Caucasian woman but he wanted to go back to Asian women. Howard asked if she ever tried to impersonate an Asian woman. She said that she did that a few times. Howard told her she’s a really good looking woman. He asked if that was a big blow to her ego. She said that it wasn’t that bad because they got to a point in their lives where it was time to split.
Howard told Karri to show them some skin. She was all covered up so she took some clothes off. She said that she has to get her boobs redone because one of the implants is encapsulated. Howard said that she has to strip down if she wants to win. Gary said she has a great body. Howard said the lower half might be better than the top. Howard said her ass is great for a 42 year old. She said she runs and she lifts weights.
Howard asked if her kids are her biological kids. She said they did come out of her. Gary asked if the 15 year old’s friends look at her weird. She said that they actually do and they’re no longer allowed to stay over at mom’s house. She said that 15 year olds are like men these days so she can’t lay out in her bathing suit in front of them. She said she knew it was trouble when one of the 15 year old’s friend asked her if she ran because she had great legs. Howard said he doesn’t get why a guy would leave a woman like this. He said that she’s really hot. He said she’s a freak of nature.
Howard asked Karri if she’s ever slept with a black guy. That was her personality question. Howard didn’t like that so he asked her how you can tell a guy is Jewish in 3 ways. She said there’s the nose, what they spend on a date and the penis. Howard said the questions were from their employee handbook. Howard also asked her what race she would exterminate if she was forced to pick one. She picked Asians because of her husband.
Karri said she brought her friend to the city with her and they’re going to have a lot of fun while they’re there. Howard asked her if she has done any lesbian stuff with her. She said that her boyfriend wants her to but she hasn’t yet. She said that she did have a first kiss with a woman a while back. She told a story about making out with a woman for the first time and how she walked around with lipstick all over her face.
Howard told Karri not to get too excited yet. He said that she hasn’t won. Karri said that Howard said she was good looking so that was great. Howard told her that her ass was her best feature.
Howard introduced the next woman. That was 38 year old BJ. Howard said that was a great name. She said it’s actually Billy Jo but she’s been known as BJ forever. Howard asked if she considers herself a cougar. She said that ti’s tough getting up to that age. Howard asked about her 3 kids. She said that she had them naturally. Howard asked how they have such good bodies after having 3 kids. BJ said she doesn’t even work out. She said she has fake boobs and lives in New Jersey. Howard said her husband entered her into the contest. She said that she’s been married since 21 and she’s only had 3 guys in her life. BJ said she has a 16, 12 and 5 year old.
Howard asked BJ about having sex in the parking lot of a Toys R Us. She said her husband got horny and they did it in the parking lot because the kids weren’t around. she said they don’t have a lot of time to do that kind of stuff. She said they did it in the front seat of a Ford Explorer. Howard asked how that works. She said that she got on his lap and did it. She said it was only about 30 seconds. She said he has a vasectomy so she doesn’t need to worry about condoms.
Howard asked BJ if they ever have sex more than once a day. She said sometimes it’s 2 but rarely 3. BJ said they don’t swing and she’s never gotten it on with another woman. Howard asked what she does for a living. She said she’s a bartender. Howard asked if she was going to show them a bathing suit or anything. She said it was winter so she didn’t have anything else on.
Howard asked BJ if she and her husband role play in bed. She said that they do that but she’s never pretended to be Asian like Karri. Howard asked if she gets hit on as a bartender. She said she doesn’t get that much. She said they have younger girls there that get hit on.
Howard asked BJ what the most embarrassing sexual experience for her was. She said that she couldn’t think of one. She said her best talent is chugging a beer in about 3 seconds. Howard asked her what she hates most about men. She said it’s jealousy, needy guys and stuff like that. Howard asked if she wishes her husband had a bigger penis. She said ”oh sure!”
Howard moved on to contestant number 3 who was 50 year old Theresa. Howard said she looks really good too. She said she was very excited to be there. She said her boobs are fake but they’re 20 years old. She has a 29 year old daughter. Howard said that’s almost as old as him. She’s married and she said that she still gets hit on. Howard said she’s a fan of the show but not a fan of Richard’s. She said that she just said that he needs to practice better hygiene. Howard said most women are shocked by Richard’s hygiene.
Howard asked Theresa how long she’s been with this one guy. She said that she’s been married 19 years but they’ve been together longer than that. Theresa said that she used to hear that her 15 year old son had people calling her a MILF and she had no idea what that meant.
Theresa said that she’s gone through menopause but she’s still able to get wet so that’s no problem. Howard asked if she swings at all. She said that they don’t but they do think about it. She said that they don’t want to risk screwing anything up. Howard said she’s had sex in an elevator and asked how she was able to do that. She said that was in his private elevator at a condo her husband owned. She said they didn’t care about the security cameras in there either.
Howard asked Theresa how young she’ll date. She said they can’t be younger than her son. She said that she’d probably have to stick to guys who are 10 years younger. Howard read about some of the places she’s had sex and she’s done it in public a lot. Howard said that not many 50 year old women have that kind of body or sex drive. Howard asked how her ass is. She said it used to be better when she worked out. Howard said he’d like to see more but she wasn’t prepared to show anything.
Howard asked Theresa some personality questions like the one about exterminating a race. She said that maybe the Turks because they have always invaded countries. Howard asked her what she’s found to be very beneficial in her life. She aid it was probably birth control pills. Howard asked her what relative she would kill for world peace if she had to. she said it would probably be her brother because he’s a great man and he’s a pastor so he’d be in heaven.
Howard said all three of them look good. He said that they’re 38, 42 and 50 years old and they didn’t have a real boob in the house. Howard said that they sag when they get older so he understands that. Howard asked if anyone wanted to show their breasts. No one was willing. Howard asked Theresa if she wanted to lift her dress at all. She did a little bit. Howard asked Robin if she wanted to show something. She had no interest in doing that either.
Howard said they had to pick a winner now and that person is going to get $5,000. Howard wanted Robin to vote first but she told him to have Fred vote instead. Fred said that they were all hot but he was going to pick Karri. He said Theresa was his second choice. He said he thinks she fits that ”cougar” description best. He said that vote could have changed if someone had gotten nude.
Gary agreed with Fred but BJ was close. He said that Karri’s ass got to him. He said it spoke to him when she took her pants off. Howard said that you don’t see many 42 year olds with an ass like that.
Howard said they had two votes for Karri so he went to Robin next. Robin said it was very difficult for her. She said that they all had great personalities but she was mesmerized by BJ’s abs so she voted for her. Howard said that they had 2 for Karri and one for BJ. Howard said he could throw it into a tie or give the win to Karri. Howard said Theresa looks amazing for a 50 year old woman. He said he’s seen a lot of women walk through there and she looks really tight. He said that BJ has great abs. He said they’re all lovely. He said that Karri got it. He said that her personality was insanely good and her ass was great. He said he would bang that girl. He said that she really fits the definition for a cougar too. He said he had to go with her as the winner.
Karri said that they all bonded in the back room so they’re all planning to go out for cocktails tonight. Howard sang a song to Karri about her win.