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Episodes tagged: crossdressing

Behold Randy Rainbow!

Episode #813 —
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A trans man used to be an escort before his transition. Now that he is hornier than ever on testosterone, he wants to try sleeping with gay men. But in his escorting days he would disassociate to get through the sessions. How can he learn to be more present in bed with cis men?  A … Read More »

With Andrew Rannells

Episode #647 —
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A woman and her husband are having a difficult year. And to top it off, he divulged that he likes to wear women’s clothes, and would like to raid her closet. She worries that this is just the first step toward a transgender identity. Do straight men ever like to wear women’s clothes? (Spoiler: Yes.) … Read More »

A gay cuckolding study with Dr. Justin Lehmiller

Episode #590 —
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A woman is worried that a couple she’s friends with will ask her and her husband to swing. How can she politely tell them that she and her husband don’t roll that way? A man’s new boyfriend is so wonderful! Their relationship is beautiful and amazing. Unfortunately, he is also a homeless, lying meth-head. How … Read More »

The CONSPIRACY to make black men gay.

Episode #437 —
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A self-professed “pervert” is married to a self-professed “Christian.” He wants to keep watching his porn in peace, she forbids it. Should he sneak to see Hump, or fess up and invite her along? A hand-wringing lesbian feels guilty whenever she gets the foot massages that turn her on so. Dan chats with Jonathan Capehart … Read More »

Wake up! It’s Mike Birbiglia.

Episode #428 —
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A husband can’t be bothered to bring his wife to orgasm. Why? It’s too much work! His hand gets tired! A man is pretty sure his nephew is gay. The rest of the family is homophobic. How can he soften the ground with the family, and let his nephew know he has support without outing … Read More »

Help! My friend is trans!!!

Episode #411 —
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A woman is shocked to learn that her best friend is a trans woman. Why did she keep it secret? Should the caller feel betrayed? Hear the tale of the French maid outfit that ruined a relationship. A college lesbian is horrified to discover that her roommate is an aggressively anti-gay Christian. A woman’s former … Read More »

It’s Bible study time…

Episode #359 —
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Dan speaks with pro-gay rights Christian John Shore about the NALT Project. Non-douchey Christians: here’s your chance to speak up. www.NotAllLikeThat.org A woman discovers (through snooping, how else?) that her boyfriend is into cross-dressing. How can she let him know she approves without letting on that she snooped? A man in a sugar mama relationship … Read More »

When Gays ATTACK!

Episode #351 —
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Her boyfriend wants it every day. She can manage 4-6 times per week but he still berates her for not putting out enough. Who’s side will Dan come down on? Here’s another gem of a boyfriend: He won’t compliment her or show any signs of affection. He hasn’t told his friends about her, and won’t … Read More »

Dad likes to wear women’s clothing. This doesn’t bother his daughter, but…

Episode #313 —
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Dad likes to wear women’s clothing. This doesn’t bother his daughter, but she doesn’t want to hear much more. (But knowing his dress size might come in handy over the holidays.) When your “straight” friend appears on a gay online dating site, does that mean he’s out?  A gay man loves to huff his boyfriend’s … Read More »

More rantings about a man named Weiner. Are garter belts inherently sexist,…

Episode #244 —
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More rantings about a man named Weiner. Are garter belts inherently sexist, and is there a male equivalent? Dan interviews Ogi Ogas, co-author of “A Billion Wicked Thoughts” in which two computational neuroscientists embark on the largest study of sexuality since Kinsey. And more. 206-201-2720 Today’s episode is brought to you by AdamandEve.com. Get 50 … Read More »