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Episodes tagged: trans gender

Planned Parenthood to the rescue!

Episode #487 —
Micro Episode with ads
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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 »

With Bailey Jay

Episode #483 —
Micro Episode with ads
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A woman’s roommate up and left without notice, leaving behind some expenses in the care of her sick, aged cat. Dan gets in full Judge Judy drag to help arbitrate this rather mundane dispute. Meanwhile, a lesbian wants her butt-plug back! She lent it to her girlfriend and then they broke up. Although things are … Read More »

Parents and their trans kids.

Episode #482 —
Micro Episode with ads
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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 —
Micro Episode with ads
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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 »

The One-Minute Wonder Show!

Episode #476 —
Micro Episode with ads
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It’s the One-Minute Wonder Show! You asked your questions in one minute or less, and Dan tried to keep his answers brief, with diminishing success. Here’s a smattering of topics: The dangers of road head, olive oil as lube, haggling with your sex worker, tingly come, excluding dog-fuckers from your orgy and so much more. … Read More »

With Parker Molloy.

Episode #475 —
Micro Episode with ads
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A man’s boyfriend went as a “slut” for Halloween. It turns out, this was a really bad idea. A woman loves getting tied up. But she also needs to touch herself to get off. So…how is this gonna work? On the Magnum, Dan chats with trans writer Parker Molloy about the challenges of transitioning for … Read More »

Families! With Ken Jennings and Brother Billy.

Episode #474 —
Micro Episode with ads
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As you gather around the Thanksgiving table to bask in the warmth and glow of your loved ones, here are some reasons you might feel thankful: Your sister’s boyfriend isn’t beating her up, your wife isn’t a transphobic Russian, your boyfriend’s father doesn’t beat him up, your mother isn’t a toxic evil mess and your … Read More »

All hail Kate Bornstein!

Episode #466 —
Micro Episode with ads
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A woman who identified as lesbian of 15 years (with a wife even,) has taken a younger, male lover. So, how is this gonna work? A man’s girlfriend insists that if and when they have kids, he will have to go through “labor simulation.” He thinks this is batty. But what does Dan Savage think? … Read More »

Trans porn star Bailey Jay.

Episode #464 —
Micro Episode with ads
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Have you ever loved someone so much, even though you’ve known them for only 6 weeks, that when they break up with you, you call a sex advice podcaster sobbing and sobbing? Meanwhile, a married man with his wife for 11 years, is working on forgiving her for cheating on him, and on opening their … Read More »

With NPR’s Peter Sagal!

Episode #460 —
Micro Episode with ads
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Dan and Peter Sagal, host of NPR’s “Wait Wait… Don’t Tell Me” join forces to discuss baptism, Jewish vs Catholic guilt, clingy, needy human doormats, and the special torture that open relationships can bring on. Peter is hilarious and delightful- this show is not to be missed. Some of it is on the Micro, all … Read More »