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Episodes tagged: trans

Bad Boys

On the Magnum: Ashley Ray on the JonBenét Ramsey case.
Episode #945 —
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A trans guy just can’t break into gay male spaces. He feels ridiculed and rejected, and ends up sitting in a corner alone while the sweaty dance party goes on around him. He used to be confident before his transition. How can he get a little of that male swagger and bed a hot twink? … Read More »

Sweet! Free therapy from Therapy Jeff.

Self Care? Sign Us Up!
Episode #941 —
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First off, we hear from a neglected third in a poorly executed threeway hook-up. He failed to advocate for himself, and the other two guys weren’t asking if he was ok, sitting on the couch, looking at his phone. How could this have gone better? And how can he get over the waves of insecurity … Read More »

Meth Baby

On the Magnum: Interview with the Cross-Dresser
Episode #930 —
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Workplace intrigue ahoy! A gay trans man who passes completely, is out to some of his co-workers but not all. Over drinks, one of his bosses told him he was bi, but not attracted to male genitals. So was this his way of acknowledging that the caller is trans, and flirting with him? Or was … Read More »

Done: Pegging IS in the Oxford English Dictionary.

On the Magnum: comedian Andy Richter
Episode #923 —
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It’s the “Overthinking It” episode! “I’ll give you $100 if you spit in my beer.” This offer was made by a random gentleman in a sushi bar to an unsuspecting lady. She declined. Would you do it? Is anything wrong here? Overthinking it? Meanwhile, a man wonders if the dubious ethics he saw in a … Read More »

Wet & Messy

On the Magnum: Peggy Orenstein on Choking Hazards
Episode #916 —
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Her man used to enjoy chewing tobacco, and it messed up his teeth. He has quit at her behest, but now he really needs to see a dentist. She doesn’t want to shame him for his nasty mouth, but she also doesn’t want to kiss him. How can she gently guide him into a dentists … Read More »

Can You Be Poly Without “Catching Feelings?”

On the Magnum: Humor writer Alexandra Petri
Episode #912 —
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A woman moved into a new house and promptly slept with her roommate. It was great sex and the caller wants a repeat. He claims he wants more as well, but then never actually takes her up on it. One night she asked if he wanted to…you know…do it, and he chose to play video … Read More »

Saline Infusion Enthusiasts Rejoice!

Episode #908 —
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You guys! We are in crisis! There are just not enough hot young women! DO. THE. MATH. A woman is dating a trans woman. Her girlfriend recently got bottom surgery, and wants to try being penetrated by an actual penis, as opposed to a toy. Should the caller allow for an open relationship to accommodate … Read More »

Interview with the Adult Baby

On the Magnum: Erika Moen on safe, soft sex toys.
Episode #900 —
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A man’s wife had to quit drinking due to a medical condition. They used to get tipsy and have wild sex. Now that she can’t drink the sex has become rote and inhibited. They plan to go on vacation together, but the caller feels that if they can’t have their free-wheeling sex, he doesn’t want … Read More »

Beer Can Blues.

On the Magnum: Two Dykes and a Mic.
Episode #897 —
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A German lesbian was propositioned by a younger grad student. (This sounds like a porno but it’s not.) The grad student was raised in a conservative environment, and it’s the first time she’s ever spoken of her female attraction. They only have a month before they both move away. Should the caller get down with … Read More »

What’s All This About Doxy-PEP?

On the Magnum: Dr. Oliver Bacon
Episode #884 —
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A man has discovered his love for wearing feminine clothing. His friends and fiancé are all supportive. But his brother- not so much. Should the caller just expect to move through the world offending people with his unconventional dress?  A gay transman has started having kinky hookups. Although he doesn’t want the intimacy associated with … Read More »