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Episodes tagged: age difference

Here's a brainteaser: If a man is into sounding, could he possibly…

Episode #125 —
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Here’s a brainteaser: If a man is into sounding, could he possibly stretch his urethra out so much that he can have the equivalent of a pussy fart, only from his dick? Facial remorse: A 23-year-man wonders if giving a facial to a “slutty” 16-year-old is a good idea. A kinky man wonders how he … Read More »

One caller has got herself a crossdressing grandpa. Another caller has got…

Episode #118 —
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One caller has got herself a crossdressing grandpa. Another caller has got himself a psycho girlfriend. Yet another caller has a boyfriend who’s ashamed of sex. And a very lucky 4-month-old has a very cool dad. Whatchoo got? 206-201-2720 This episode was brought to you by Audible.com. Download a free audio book of your choice … Read More »

In the weepiest call ever, a woman breaks up with her boyfriend rather than…

Episode #103 —
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In the weepiest call ever, a woman breaks up with her boyfriend rather than let him leave his children for her. But he also sounds like a creep. What is the ethically correct thing to do when your friend with benefits falls in love with you? When a man refers to his friends as “buddies,” … Read More »

A horndog keeps dating ladies who don't want to have sex. Now he's…

Episode #99 —
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A horndog keeps dating ladies who don’t want to have sex. Now he’s bugging out. A nonorgasmic woman is making a lot of noise during sex, but she’s not closing the deal. How can she talk about it with her boyfriend? A gay man with a cute voice freaks out and clams up when faced … Read More »

Two tales of parental meddling: A woman is in a happily open relationship…

Episode #96 —
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Two tales of parental meddling: A woman is in a happily open relationship with her boyfriend. But her parents don’t know they’re both free to see other people. What happens when her dad catches the boyfriend courting another lady? Another woman is in a blissful relationship with a man 20 years her senior. But her … Read More »

We open the show with a couple of cute fellas who just can't seem to…

Episode #92 —
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We open the show with a couple of cute fellas who just can’t seem to meet people, despite their scorching hot looks and charming personalities. Does scat reduce (or increase) life expectancy? She’s digging him. He’s digging her. But she wants kids and he hates kids. What does their future hold? Cuckoo for cuckolding: Enter … Read More »

Down there hair: Must we remove it? Bad date: After a woman endures a…

Episode #89 —
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Down there hair: Must we remove it? Bad date: After a woman endures a super-creepy date, the fellow is still trying to contact her and pries her friends for info about her. How can she get rid of him? Is there something she should have done differently to give him the message? Unhappy endings? A … Read More »

The 34-year-old Dan Savage tackles the following questions: If you're…

Episode #88 —
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The 34-year-old Dan Savage tackles the following questions: If you’re into older guys, will you always be into older guys? Like even when you’re old? And is there anything wrong with that? What’s so very wrong with young people getting married, anyway? How can a lesbian swirling in lesbian psychodrama develop a bionic bullshit detector? … Read More »

Blood and Sugar: Today's episode spans many topics, including ladies…

Episode #87 —
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Blood and Sugar: Today’s episode spans many topics, including ladies who get compensated for their sweet time. One caller is falling in love with her sugar daddy. Another caller has a fuck buddy who has suggested that he pay her for her services; how much should she charge? A fit gay man has fantasies of … Read More »

He thinks he's a 61-year-old sex machine; she just likes the money he…

Episode #84 —
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He thinks he’s a 61-year-old sex machine; she just likes the money he pays her. Should she keep pretending to enjoy the oral sex her sugar daddy insists on giving her? • Clark Kent: Hear the charming but confusing tale of a couple who maintain both a real and online relationship with each other. • … Read More »