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Episodes tagged: three-ways

So many sex toys!

Episode #551 —
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A man and a woman used to date, but now they’re just friends. The woman got married and doesn’t want her rich husband to know that she used to date the caller. Is it because she’s embarrassed that the caller doesn’t make enough money? From three-way to third wheel…a gay man with a long term … Read More »

Sex Toy Review: Silver Bullet!

Episode #535 —
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“Boyfriend, boyfriend, there’s a lump in your testicle!” Should the caller deliver this news bluntly or keep her discovery to herself? A mother’s 9-year old son wants to be a stripper when he grows up. How can this mom advise him and keep her cool? Erika Moen from Oh Joy Sex Toy is on for … Read More »

The pleasures and dangers of choking.

Episode #533 —
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A man’s friend came out when they were in high school. Now after a sojourn to the desert to “pray away the gay” the tortured closet case is “church hunting for a bride.” Can his pal talk him out of this? A woman’s co-worker tried to kiss her at work, despite her unrelentingly professional demeanor, … Read More »

No on Prop 60!

Episode #523 —
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On the worst birthday EVER, a woman learns that her beloved long distance boyfriend…has a wife. If the wife asks her, should she lie for him? A man’s friend is dating a guy who gets coked up, turns the photos of her face-down and hires prostitutes to sleep with him in their shared bed. How … Read More »

With Cheryl Strayed

Episode #518 —
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A woman is horrified to discover her new boyfriend’s disgusting habit. This habit truly is one of the most revolting things we’ve ever heard, and you do know that we’ve heard a LOT, right? You’ll have to listen to find out what it is. A woman and her husband want to take the plunge and … Read More »

With the creators of “Tickled” the movie.

Episode #509 —
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A woman is in a new relationship with a wonderful man! But! His ex keeps coming around leaving love notes, Victoria’s Secret receipts and otherwise marking her territory. How can the caller flush out the intrusive ex? What is the etiquette in asking out a guy at the gym to join you and your husband … Read More »

Planned Parenthood to the rescue!

Episode #487 —
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A mature 18 year-old has somehow failed to tell her real age to her new boyfriend who thinks she’s at least 20. How can she come clean? A man is totally into being cuckolded. Does his girlfriend have to tell her other lovers that they are part of a bigger picture? We are honored to … Read More »

Let’s hear it for companionate marriage!

Episode #486 —
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A woman is thinking of surprising her boyfriend with another woman to have a three-way with. Can Dan talk her out of it? An evenly bisexual man had to come out at his macho job as gay when was engaged to a man. Now that he’s dating a woman, does he have to come out … Read More »

Parents and their trans kids.

Episode #482 —
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A young woman is about to embark on a three-way with her boyfriend and another man. How can she make sure the experience isn’t demeaning? A gay man has incest fantasies. How can he find a man willing to role play a father-figure? A married woman and her husband prefer to use condoms. So why … Read More »

Second Opinion with Mallory Ortberg.

Episode #480 —
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In two separate calls, straight men are harassed by their gay male friends. One caller had his buddy drunkenly grope him. The other’s pal assails him with aggressive sexual innuendo. Knock it off fellas! A married woman has a husband who doesn’t trust her. She comes home late from her bar job and he assumes … Read More »