Best Crossdressing Podcasts (2024)

1
My Wife Wants Me to be Her Crossdressing Sissy | Extreme SPH Roleplay Chat (MF) 9:41

1h ago9:41

9:41

This session involves an arouser member and chat host Kiki Miller. The scene begins as Kiki is asked by a member to roleplay that his wife is trying to turn him into her submissive girlfriend even though he’s a guy. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerses himself in a fantasy he explo…

1
Lexi Hudson - Crossdressing Interview 1:21:46

7h ago1:21:46

1:21:46

Send us a text In this engaging episode of the Girl Life Podcast, host Maddie Taylor welcomes Lexi Hudson, a vibrant member of the LGBTQ+ community and an organizer of the wildly popular Wildside event. Lexi shares her journey of self-discovery, from her childhood in Texas to her exploration of gender identity and dressing. She discusses the import…

1
How to talk to your partner about crossdressing, feminization, and sissy desires 31:13

18d ago31:13

31:13

Today’s episode is inspired by a listener who wants help talking with a partner about feminization desires. Anita wants us to say something that will change the minds of wives or girlfriends who don’t like feminization with their partner. We don’t know that we can change minds, but this episode covers topics like: What do cisgender, heterosexual wo…

1
Japan election, China-Taiwan tensions, Nobel Peace Prize, crossdressing crime and Japanese car names 19:04

12d ago19:04

19:04

In this episode, Jeff covers election season in Japan, growing tensions between Taiwan and China, an atomic bomb survivors' group receiving the 2024 Nobel Peace Prize, a cross-dressing man causing a stir at a Nagoya bathhouse and readers' thoughts on odd Japanese car names. Tune in for a mix of serious news and lighter, quirky topics with commentar…

1
So you want to be a service submissive. What does that mean to a Femdom Mistress? 31:43

18m ago31:43

31:43

Every Femdom hears this: “Mistress I want to serve you.” What does that mean? There are many ways for a sub to serve a Mistress. There is no arbitrary ‘right’ way to have a D/s relationship. Part of BDSM negotiation means making sure that each person is in agreement about roles, expectations, activities, etc. Topics in this podcast episode include:…

1
Mawwiage Story: The Fourth Fragment of "The Canterbury Tales" 1:18:50

2h ago1:18:50

1:18:50

Send us a text Toni, our resident medievalist gal about town, has returned to give us more of that sweet sweet Chaucer content!! In the Fourth Fragment, we're talking Mawwiage: What Bwings Us Togevver, and what tears us apart. Wily Wives and Horrific Husbands abound! As always, we are: -Asking with all the love in our hearts that you leave us a rev…

1
Episode 115 (Highs And Lows) With My Buddy John 2:55:17

1h ago2:55:17

2:55:17

https://linktr.ee/SynThetic1369 Email: originalsyn1369@gmail.com Send us a text Support the showBy Syn Thetic

1
Nov. 8, 2024: Customer harassment crackdown, Mount Fuji light rail, bike law penalties, new train safety measures and missing student update 20:42

18h ago20:42

20:42

Welcome to another episode of Japan This Week, your weekly roundup of trending news stories from Japan Today for Nov. 8, 2024.In this week's episode:NATIONAL: Customer harassment crackdown (1:01 - 5:40)Japan's service industry workers are facing increasing abuse from customers. Major companies like Ito-Yokado are implementing manuals and training t…

1
Episode CCXLIV: The execution of Peanut & Fred & Erection Special 1:12:20

2h ago1:12:20

1:12:20

Squirrel and Raccoon Execution Discussed Lamentably, we discussed the case of a squirrel named Peanut and a raccoon named Fred, who were executed by the State of New York. They criticized the government's priorities, pointing out that the state could not handle crime committed by migrants but could dispatch 12 officers to deal with a squirrel. We c…

1
Do transwomen get you horny? 29:20

16m ago29:20

29:20

We hear all your secrets and sexual fantasies. A lot of our callers fantasize about sex with a transwoman. Today’s episode explores this. Topics include: How popular is the sex with a transwoman fantasy? Many men ask, am I straight if I want to suck the cock of a transwoman? To start off, a quick overview of names for transwomen and how to be respe…

1
The Nerd and the Succubus: "Amore Dure: Passages from the Diary of Spiridion Trepka," by Vernon Lee 59:16

3d ago59:16

59:16

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Pod bestie Will is back to tell us about Vernon Lee's tale of Italian succubi and academics with no sense of self-preservation! As always, we are: -Asking with all the love in our hearts that you leave us a review or tell a friend about the show <3 -Accepting …

1
Nov 1, 2024: Political turmoil, Tokyo’s green space battle, tragic crime and Meta's fake ad scandal 18:45

6d ago18:45

18:45

Welcome to another episode of Japan This Week, your weekly roundup of trending news stories from Japan Today for Nov. 1, 2024.This week, we dive into the aftermath of Japan's recent general election, which has left the ruling coalition in disarray and no party with a majority. We also explore the heated controversy around Tokyo's Jingu Gaien Park r…

1
Seduced By My Sister In Law Behind My Wife's Back | Affair Roleplay Chat (MF) 13:29

6d ago13:29

13:29

This roleplay chat session involves an arouser member and chat host Kiki Miller. The scene begins as Kiki is asked by a member to roleplay that she’s the flirty sister in law who decides to make her move on her sister's husband over the holidays. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerse…

1
Episode CCXLIII: more brain rot 1:01:14

20h ago1:01:14

1:01:14

The gang discussed a problematic Twitter account and a TikTok account thanking Stalin. Jay expressed concerns about a proposed amendment to the Ohio Constitution. The conversation then shifted to various topics, including a British woman marrying a 300-year-old dead Haitian pirate, a British singer marrying a 300-year-old dead man, and the challeng…

1
What does it mean to be submissive? 30:51

1d ago30:51

30:51

This episode is inspired by a blog post written by our friend and fellow Mistress, Ms Demi. Listen in as three Pro Domme’s talk about the submissives in our lives. What do Femdoms have to say about power exchange and those who need to submit to powerful, dominant women? Mistress Olivia kicks off the conversation with a quote by Mistress Demi: “Subm…

1
Italian Witchcraft and a Mad Madonna: Alicia Ramsey's "A Modern Circe" 1:02:24

5d ago1:02:24

1:02:24

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Beloved of the show Jessica Camilli (@Rapid.Eyes , https://rapideyes.art/) returns for a tale of witchcraft, transformation, and feminine revenge! Join us as we explore Alicia Ramsey's spellbinding 1919 short story, "A Modern Circe." As always, we are: -Asking…

1
Oct. 24, 2024: Crime, carbon emissions and used phones in latest Japan news 23:27

5d ago23:27

23:27

In this episode, we cover the rise of organized crime and robberies in the Kanto region driven by social media apps, Japan's nuclear energy resurgence to tackle carbon emissions and a spike in used smartphone sales as consumers push back on constant new releases.Plus, we discuss efforts to find Claudio Worm, a missing German tourist, and give liste…

1
Heidi Phox - Girls Wanna Know (8:00) 8:00

12d ago8:00

8:00

Send us a text Join us for a short listen where Heidi Phox answers questions from the community. Heidi discusses her interactions with her wife, neighbors and children and much more. Check out www.mygirllife.com Write to Maddie at maddiesometimes@gmail.comBy Maddie Taylor

1
Bisexual Grindr App Hook Up with Dominant GF | Roleplay Chat (MMF) 10:35

13d ago10:35

10:35

A man roleplays that he is being coached by a his dominant girflriend to sign up to a gay dating app site. His girlfriend provokes him and challenges him to post pictures of himself to find a hook up for the evening so she can watch. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerses himself in …

1
Uterine Fury and Bloodlust: "The White Maniac," by Mary Helene Fortune 58:17

12d ago58:17

58:17

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! It's a bloody good time with our official Vampire Correspondent, Galen, as we help ourselves to Mary Helene Fortune's delicious tale of forbidden appetites and uterine fury, "The White Maniac." As always, we are: -Asking with all the love in our hearts that yo…

1
Dominant GF Turns Boyfriend Into Her Maid | Forced Feminization Roleplay Chat (MF) 12:51

21d ago12:51

12:51

A man roleplays that his bossy girlfriend goes away on vacation for a week. However, in order to keep him obedient as her slave while she's away her domme girlfriend is invted to stay with him at the house. The domme proceeds to turn her boyfriend into a submssive maid for the day and madness ensues. This is an adult ASMR conversation where a man f…

1
Episode CCXLII: Winds of change in Portland, Hamtramck big sad 1:05:09

15d ago1:05:09

1:05:09

Hamtramck's Pride Flag Controversy and TensionsWe discussed the city of Hamtramck, Michigan, which has become more diverse with immigrants from various backgrounds. The city's decision to block the display of the pride flag on city property has angered the LGBQT+ community and some allies, who feel betrayed by the lack of support they provided to t…

1
It’s LOCKTOBER: are you ready for chastity? 25:28

16d ago25:28

25:28

Basically, Locktober is a month-long chastity challenge. Typically, it involves those who identify as submissive and wear a chastity cage the entire month of October. This episode is about orgasm delay, orgasm denial, chastity training, and why a Femdon enjoys having a chastity pet. Topics include: What is chastity? What is Locktober? Why would som…

1
Episode 114 Me And My Buddy John (Broken Edit) 1:52:23

27d ago1:52:23

1:52:23

I had an amazing time with my pal John who I met at bus-ees. Me being a moron, I messed up the save soooo, I lost the middle of the conversation as we took breaks. The length of the pod was over 3 and a half hours but now it's a bit shorter than that. so enjoy. https://linktr.ee/SynThetic1369 Email: originalsyn1369@gmail.com Send us a text Support …

1
Undead Trad Wives: "The Nature of the Evidence," by May Sinclair 1:09:42

19d ago1:09:42

1:09:42

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Frisky flappers and undead trad wives abound in May Sinclair's "The Nature of the Evidence"--join Grace & new pal of the pod Benjamin Braman as they explore this tale of ghostly marital trouble and a hauntingly bad time in bed. If you'd like more of Benjamin, …

1
Megumi Yokota, Japan best for Condé Nast, R-rated Quantas flight, villain queen & Japan rail origins 21:18

19d ago21:18

21:18

In this episode, Jeff and Kong dive into stories of heartbreak, excitement and controversy — including a mother's ongoing search for her abducted daughter, Japan's #1 ranking as the best country to visit, an in-flight movie mishap and Netflix's new pro wrestling series. They also profile the British engineer who helped launch Japan railways over 15…

1
Heidi Phox Interview (1:08:40) 1:08:40

20d ago1:08:40

1:08:40

Send us a text In this episode of My Girl Life podcast, host Maddie Taylor interviews Heidi Fox, a prominent figure in the cross-dressing community. Heidi shares her journey of self-discovery, the challenges she faced in her relationships, and the support she received from her wife. The conversation delves into Heidi's early life, her experiences w…

1
Episode 113- Stories From The Shop 50:57

1M ago50:57

50:57

https://linktr.ee/SynThetic1369 Email: originalsyn1369@gmail.com Send us a text Support the showBy Syn Thetic

1
The Sexy Secretary Seduces Her Boss for a Promotion | Office Roleplay Chat (MF) 12:53

27d ago12:53

12:53

A man roleplays that he is the boss in a coprorate office when his slutty secretary decides to seduce him in order to be promoted to be his personal assistant. She will do anything he asks of her to get closer to him. Anything. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerses himself in a fant…

1
Perverz Pleasures - Perth's Kinky Munch & Events S02E23 44:03

26d ago44:03

44:03

Welcome to Kinky Confessions! In this episode, we're diving deep into the vibrant world of Perth's kink scene with the fabulous Kate and Sass from Perverz Pleasures. These two are the masterminds behind a series of incredible kink events that offer something for everyone. Whether you're a seasoned kinkster or just curious to explore, Perverz Pleasu…

1
Episode CCXLI: the docks, scab consumption & urine distillation & more 59:00

23d ago59:00

59:00

Wage Increase, Strike, Automation, and Economic ImpactThe group discussed the recent wage increase for dock workers and the potential consequences of their strike. Angel expressed concern about the potential for supply chain disruptions and the impact on the economy, while jay acknowledged the importance of unions and the need for fair compensation…

1
Are you worried about topping from the bottom? BDSM advice from your Femdom hosts. 34:29

23d ago34:29

34:29

We hear from a lot of subs who are worried about topping from the bottom. That’s a BDSM term that means a submissive who flips the power dynamic in a way that is disrespectful, rude or otherwise irritating to the Dominant. Some subs hear that and worry that they are topping from the bottom if they make ANY requests of the Domme. We don’t want you t…

1
Volume Three - Mary Shelley's Prophetic Apocalypse: "The Last Man." 1:38:52

26d ago1:38:52

1:38:52

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Mary Shelley: the gothic queen of our hearts, the immortal creator of Frankenstein herself. But what about the time she decided to end the world? Join Grace and Maddie Wood as they explore VOLUME TWO of Mary Shelley's "The Last Man," the first piece of modern …

1
Oct. 4, 2024: Japan new PM, price hikes, Tokyo drinks ban, death row lawsuit and bullet train 60th 24:31

26d ago24:31

24:31

Welcome to another episode of Japan This Week, your weekly roundup of trending news stories from the Japan Today website.This week, Jeff Richards runs solo to bring you the latest stories and reader reactions, including Japan's new prime minister Shigeru Ishiba, prices rising yet again across the country, Tokyo's Shibuya and Shinjuku districts’ exp…

1
A M.I.L.F Hotwife Goes Bull Hunting | Polyamory Roleplay Chat (MMF) 11:02

1M ago11:02

11:02

A man roleplays that he is married to a M.I.L.F Hotwife. They finally have a night to themselves and decide to go bull hunting together at the Four Seasons Hotel Bar in Chicago. A more discreet and upper class environment to find a third. Listen to the full story to find out how hardcore this scene will end between a husband, wife and a bull. This …

1
Episode CCXL: Paulie P's stonks dump, Mayor Tiff, Oakland & more 45:22

1M ago45:22

45:22

The gang discuss the catastrophic impact of Hurricane Ian, described as a once-in-a-generation storm. They share details about the widespread devastation, including towns being wiped away, record-breaking rainfall, and millions left without power across multiple states. The hurricane maintained its strength even after making landfall, exacerbating …

1
Power, money, BDSM, and Femdom: interview with author Jane Boon 39:35

1M ago39:35

39:35

We continue our conversation with author Jane Boon. Jane’s first novel Edge Play is about an investment banker who becomes a Pro Domme via her Pro Domme friend Erika … and this second book focuses on Erika. Both books show women coming into their own personal power. Jane Boon tells a lively, interesting story and even without our favorite Femdom an…

1
Volume Two - Hamster Wheel of Doom: Mary Shelley's "The Last Man" 1:25:15

1M ago1:25:15

1:25:15

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Mary Shelley: the gothic queen of our hearts, the immortal creator of Frankenstein herself. But what about the time she decided to end the world? Join Grace and Maddie Wood as they explore VOLUME TWO of Mary Shelley's "The Last Man," the first piece of modern …

1
Sept. 27, 2024: Noto floods, Japan vs China and Russia, lame ducks, death penalties and e-scooters 28:51

1M ago28:51

28:51

Sept. 27, 2024 — In this episode, Jeff and Kong discuss the natural disasters plaguing the Noto Peninsula, airspace breaches of Japan by China and Russia, the latest political meeting between Prime Minister Kishida and President Joe Biden, the treatment of death-row inmates in Japan and the question of capital punishment plus an update on electric …

1
Cuckholdress Roleplay Chat | Humiliated by The Bull & My Hotwife (MMF) 11:42

1M ago11:42

11:42

A man roleplays that he is a cuck and has a girlfriend who loves cheating on him and telling him about all the things she does to humiliate him behind his back. They end up engaging in a threesome in the most unexpected way. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerses himself in a fantasy…

1
Episode 112 Politics, Right-Wing Conservatives Falling Apart and weird Liberal Behaviors 1:39:13

2M ago1:39:13

1:39:13

https://linktr.ee/SynThetic1369 Email: originalsyn1369@gmail.com Send us a text Support the showBy Syn Thetic

1
Episode CCXXXIX: Conspiracy Corner V w/professor Dave 1:15:54

1M ago1:15:54

1:15:54

Professor Dave - a regular contributor to the channel - has returned for our fifth installment of Conspiracy Corner. For this one, we take you to the Mile High City & its strange international airport. Receipts below. We thank professor Dave for joining us on a fun adventure. We encourage you to let professor Dave know he really ought to start that…

1
What happens after Edge Play? Author Jane Boon tells us about her new BDSM novel Bold Strokes 33:56

1M ago33:56

33:56

Money, power and sex … specifically kinky sex … are the themes of today’s episode with author Jane Boon. Jane is the author of the Femdom themed novel Edge Play and today she’s here to talk about her newest novel Bold Strokes. We highly recommend both of Jane's books. In fact, if you’re submissive, here’s your order: “Read Edge Play and Bold Stroke…

1
Kristy's Crossdressing Journey S02E22 41:03

1M ago41:03

41:03

In this insightful podcast episode, courageous Kristy shares her personal experiences as a crossdresser. With raw honesty, she delves into the complexities of her identity, exploring both the exhilarating highs and the challenging lows that come with living authentically. Kristy candidly discusses the emotional rollercoaster of navigating societal …

1
Volume One - From Frankenstein to the End of the World: Mary Shelley's "The Last Man" 1:20:16

1M ago1:20:16

1:20:16

Send us a text We HAVE MERCH! Help support the show with a rad shirt or mug or sticker!!! Mary Shelley: the gothic queen of our hearts, the immortal creator of Frankenstein herself. But what about the time she decided to end the world? Join Grace and Maddie Wood as they explore Mary Shelley's "The Last Man," the first piece of modern apocalypse fic…

1
Sept. 20, 2024: Marijuana criminalization, whale meat, elders over 100, Shogun and Japanese sushi 25:46

2M ago25:46

25:46

In this episode, Jeff and Kong dive into topics ranging from Japan's upcoming cannabis laws to the resurgence of whale meat in Japan and record-breaking Emmy wins for a Japanese period drama. Plus, they tackle Japan's aging population and sushi chefs earning more overseas.Timestamps for the Main Stories:[0:00 - 0:11] – IntroJeff introduces this wee…

1
Episode 111 A Sexual Retail Therapist 52:54

2M ago52:54

52:54

https://linktr.ee/SynThetic1369 Email: originalsyn1369@gmail.com Send us a text Support the showBy Syn Thetic

1
Femdom Chat | Spiked Drinks and Spankings (TPE & FLR) 13:05

2M ago13:05

13:05

A man roleplays that he meets a mysterious women at a bar. She picks him up and then puts something in his drink.. He wakes up naked tied to her bedroom and a total power exchange begins between them both. This is an adult ASMR conversation where a man finds a female partner to roleplay chat with and immerses himself in a fantasy he explores online…

1
Girls Wanna Know - Jacquelyn James (9:32) 9:32

2M ago9:32

9:32

Send us a text Jacquelyn James answers questions from the community! Jacquelyn leaves nothing on the table with her answers about her crossdressing to full male to female transition. (9:32) Check out www.mygirllife.com Write to Maddie at maddiesometimes@gmail.comBy Maddie Taylor

1
What makes a sissy purge? And how to avoid crossdresser purging cycles. 33:30

2M ago33:30

33:30

This episode is inspired by a question from a crossdresser but we hear many people in the kink community talk about the impulse to throw away sex toys and other kinky things. Why? Well, anyone who is into things that aren’t considered ‘mainstream’ can feel the wrong kind of shame or fear of being discovered by family, friends or work associates. Th…

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Crossdressing Podcasts

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