#448 Bottoms Up: Exploring Anal Play, Training, and Fisting
Shameless Sex26 Aug 2025

#448 Bottoms Up: Exploring Anal Play, Training, and Fisting

Let's Get Real About Anal: Breaking Down Fears and Unlocking Pleasure Are you ready to talk about the butt? Like, really talk about it? Join us on this episode of Shameless Sex as we dive into the world of anal sex with Jamie Joy, a certified sex educator and self-proclaimed "hungry slut for freaky fantasies". With over a decade of experience in spreading joy, consent, and pleasure, Jamie is here to dispel the myths and misconceptions surrounding anal sex and give you the lowdown on how to make it a pleasurable experience for all involved. Here's what you can expect to learn from this episode: • How Jamie's journey in the field of sexuality led them to become a leading expert in anal play • The most common fears and concerns people have about anal sex (yes, poop is on the list!), and how to overcome them • The benefits of anal plug training and how it can help first-timers ease into anal play • Tips and techniques for smooth insertion, whether you're using a plug, dildo, or something a little more... natural • Jamie's favorite anal toys and why they're obsessed with them (hint: it's not just about the butt) • An introduction to anal fisting, including tips and techniques for those curious about trying it (because, why not?) By listening to this episode, you'll gain a deeper understanding of the complexities and joys of anal sex, and how to approach it with confidence and curiosity. Whether you're a seasoned pro or just starting to explore, Jamie's expertise and enthusiasm will leave you feeling empowered and excited to take your pleasure to the next level. So, are you ready to unlock the secrets of anal sex and discover a world of unbridled pleasure? Join us on this episode of Shameless Sex and get ready to have your mind blown (and your ass explored)! Find Jamie Joy on Instagram @thebadjewboy or their website http://www.jamiejoy.com to learn more about their work and how to connect with them. ⁠⁠⁠Join us for our next Shameless Sex retreat in the Coachella Valley, CA September 11th-14th: ⁠⁠⁠⁠⁠⁠⁠⁠https://tinyurl.com/49b9fx8b⁠⁠⁠⁠⁠⁠⁠⁠ Get premium access to our behind the scenes episodes here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://shamelesssex.supportingcast.fm⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Do you love us? Do you REALLY love us? Then order ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠our book⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ now! Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠shamelesssex.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to snag your copy Support Shameless Sex by sending us gifts via our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Amazon Wish List⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Other links: Get 45% off our favorite (super hot) ethical porn with code SEX45 at ⁠⁠⁠https://erikalust.com⁠⁠ Get 10% off happy, healthy, soaking wet bits with code SHAMELESS at ⁠⁠⁠vb.health⁠⁠⁠ Get 15% off any annual membership at ⁠http://Masterclass.com/shameless Get 10% off + free shipping with code SHAMELESS on Uberlube AKA our favorite lubricant at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://uberlube.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get 10% off while learning the art of pleasure at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://OMGyes.com/shameless⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get 15% off all of your sex toys with code SHAMELESSSEX at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://purepleasureshop.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Episoder(557)

#502 Premature Ejaculation and How to Last Longer In Bed

#502 Premature Ejaculation and How to Last Longer In Bed

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#501 Sexual Inexperience & How to Become More Confident with Celeste and Danielle

#501 Sexual Inexperience & How to Become More Confident with Celeste and Danielle

In this episode, I’m joined by repeat guests Danielle Harel, Ph.D., and Celeste Hirschman, M.A., founders of the Somatica® Institute and creators of the Somatica® Method of sex and relationship coachi...

1 Sep 1h 2min

#500 Why Your Pleasure Needs Your Surrender with Mama Gena

#500 Why Your Pleasure Needs Your Surrender with Mama Gena

In this episode, we’re joined by Regena Thomashauer—better known as Mama Gena—to explore the transformative power of surrender, pleasure, and living fully on your own terms. Regena is the founder of ...

25 Aug 58min

#499 The Couple’s Guide to Aging & Intimacy with Dr. Castillo

#499 The Couple’s Guide to Aging & Intimacy with Dr. Castillo

We talk a lot about long-term couples growing together emotionally—but what happens when their physical selves begin to change, too? As we age, our bodies change, and those changes can have a real im...

18 Aug 1h 16min

#498 Get Nasty: Sex, Pleasure & Resistance with Ericka Hart

#498 Get Nasty: Sex, Pleasure & Resistance with Ericka Hart

What happens when we stop accepting the stories we’ve been taught about sex, gender, bodies, desire, and pleasure—and start questioning who those stories actually serve? In this episode, we’re joined...

11 Aug 1h 5min

#497 Let's Talk About Butt Stuff with Alex Hall

#497 Let's Talk About Butt Stuff with Alex Hall

Happy Anal August! Anal sex is one of the most talked-about—and most misunderstood—sexual experiences. Some people absolutely love it, while for others it's a firm no. So what makes the difference? Is...

4 Aug 1h 13min

Bonus: What Really Happens on a Sexy Cruise

Bonus: What Really Happens on a Sexy Cruise

This bonus episode was recorded during a fabulous female-led (meaning women make the first move) hedonism meets glamour cruise in the gorgeous Mediterranean put on by Killing Kittens. For six days and...

31 Jul 29min

#496 What Everyone Should Know About Eating P***y with Shaun Galanos

#496 What Everyone Should Know About Eating P***y with Shaun Galanos

Why are some people so against eating pussy? In this episode, we dive into the conversation happening around masculinity, pleasure, and what’s really behind people’s attitudes toward giving and receiv...

28 Jul 1h 29min

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