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PODCAST

Awkward Pillow Talk

VirginitySnatchers.com

Sex is awkward, funny, and sometimes downright intimidating, but it doesn’t have to be. At Awkward Pillow Talk, we bring those conversations out of the shadows and into the spotlight, making it easier for everyone to talk openly about their desires, needs, and experiences. Hosted by madly-in-love swingers and content creators Jason and Stephanie Class, we dive into everything from anxiety to orgasms, awkward sex stories, and beyond. Let’s break the stigma—because everyone does it, so let’s talk

society & culture relationships

All Episodes

24:26

Awkward...First Time Jitters

Awkward Pillow Talk ·

2025/09/16

On this episode of Awkward Pillow Talk, Jason and Stephanie Class get real about one of the biggest hurdles couples face when stepping into the lifestyle (or anything outside the “relationship norm”): first time jitters.From religious shame and outside judgment to nerves about being seen and setting unrealistic expectations, they share their own stories of awkward beginnings—everything from angry pre-meet moods, to walking out of house parties through the back door, to that unforgettable “glory hole

en

51:07

Awkward…Data-Driven Boners (featuring FirmTech CEO...

Awkward Pillow Talk ·

2025/09/04

Awkward…Data-Driven Boners (featuring FirmTech CEO Dr. Elliot Justin) + Virgins 22 & 23In this episode of Awkward Pillow Talk, Jason and Stephanie sit down with Dr. Elliot Justin, founder and CEO of FirmTech, to talk about the world’s first erection analytics ring. This sexual health wearable tracks erections, improves performance, and even provides early warnings about potential cardiovascular risks. It’s sex tech that could literally save lives.We also share the stories of Virgin #22 and

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32:59

Awkward...Nude Beach Review

Awkward Pillow Talk ·

2025/07/11

We’re back, baby — and we’ve got tan lines (or lack thereof), bug bites, and awkward boner stories to prove it. In this extra-real episode, we catch you up on everything from writing The Awkward Couple’s Guide to Getting Weird to surviving a Florida mosquito massacre in the name of nudity. We give you the honest, unfiltered breakdown of our recent trips to Florida’s top clothing-optional beaches — Playa Linda, Blind Creek, and Haulover — and explain what to expect (hint: it involves spiders,

en

0:35

Awkward...Update 05/13/25

Awkward Pillow Talk ·

2025/05/13

We broke our camera! Weve been MIA, and thats because we broke our main tool to shoot the podcast.We're taking this time to realign. We will be back! In the meantime, we'd love to keep hearing from you! Visit us at VirginitySnatchers.comSupport this podcast at — https://redcircle.com/awkward/donations

en

45:15

Awkward...Stories about Hedo with Chris Santilli

Awkward Pillow Talk ·

2025/03/25

🎙️ Inside Hedonism II: Lifestyle, Swingers, and Travel Secrets with Author Chris Santilli | Awkward Pillow Talk PodcastIn this episode of Awkward Pillow Talk, hosts Jason and Stephanie Class welcome legendary Hedonism II expert and author Chris Santilli to dive deep into the wild world of adult travel, swinger resorts, and lifestyle vacations in Jamaica. 🌴Chris has been to Hedonism II over 70 times since 1985 and shares hilarious, honest, and jaw-dropping stories from the world’s most notorious

en

44:57

Awkward… A March Festivus (The Airing of Grievances)

Awkward Pillow Talk ·

2025/03/13

Awkward Pillow Talk – Awkward… A March Festivus (The Airing of Grievances)Welcome back to Awkward Pillow Talk! This week, Jason and Stephanie are getting real—no filter, no meds, and definitely no holding back. From life updates to frustrations, friendships lost, and the search for real connections, it’s time for a good ol’ Festivus-style airing of grievances.We’re diving into:🔥 Why we ditched anxiety meds and what’s changed (spoiler: a lot)🔥 A USMC Vet owned company selling an AMAZING new

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48:38

Awkward...Penguins and Pocket Pussies

Awkward Pillow Talk ·

2025/03/03

This episode is a wild one! We welcome back the hilarious and unfiltered AskAshley479, who never holds back. We dive into everything from her solo trip to Aruba (where she got bitten by a penguin) to the struggles of being a content creator in the adult space—like constantly fighting against platform bans and dealing with clueless messages from fans.We also chat about the weird world of social media censorship, why some creators get away with showing everything while others get flagged for existing,

en

44:47

Awkward...and Miss Behavin

Awkward Pillow Talk ·

2025/02/14

We had an absolute blast chatting with @missbehavinxoxo—hilarious, sexy, and completely unfiltered! From wild industry stories to balancing life as a parent, we cover it all. Don’t miss this one!💦 Check out her Intimaly toy! → Feel MissBehavin📅 Premieres Thursday at 7 PM—Set your reminders!👀 Follow Miss Behavin everywhere:OnlyFans🔹 Paid: @missbehavinxoxo🔹 Free (No Nudity): @missbehavinxoxo_freeX (Twitter)🔹 @missbehavinxo (No XXX content unless blurred!)Instagram🔹 @missbehavinxoxo🔹

en

28:44

Awkward...Initiation - A Real Couples First Time...

Awkward Pillow Talk ·

2025/02/03

Awkward… Initiation - A Real Couple’s First Time Swapping with Jason and Stephanie🔥 Watch the Full Video Now ➡️ VirginitySnatchers.comIn this episode of Awkward Pillow Talk, we finally document something we’ve been working toward for a long time—a real couple’s first time swinging! We’ve always welcomed first-timers, but this time, we wanted to capture every awkward, exciting, and steamy moment.👀 What to Expect in This Episode:✅ A couple’s journey from curiosity to taking the plunge✅ How we vet

en

37:03

Awkward...From Vanilla to...Spicy?

Awkward Pillow Talk ·

2025/01/16

Ever wondered how a shy, naïve, barely-ever-touched-a-vibrator girl transforms into a full-on, sex-positive content creator? Look no further—Stephanie’s dishing all the details (and Jason’s soaking up the glory) on this extra-revealing episode of Awkward Pillow Talk! We’re talking everything from hush-hush upbringings to the first time Steph dabbled in girl-on-girl. Spoiler alert: it’s not always a straight line from “I might try a vibrator” to “Hand me that strap-on.”You’ll also hear about our

en

34:28

Awkward... 2025 The Year Of The Ho

Awkward Pillow Talk ·

2025/01/02

Happy New Year, and welcome to 2025: The Year of the Ho! 🎉 In this episode, Jason and Stephanie dive into the wild holiday chaos, juicy neighborhood gossip, and the ongoing struggles of being the most talked-about couple in the PTO. From navigating nosy neighbors and judgmental glances to sharing our thoughts on how our unconventional lifestyle makes us stronger as a family, we’re not holding back.We also talk about:• How we separate work from family life 💼➡️👨‍👩‍👧‍👦• The challenges and rewards

en

24:25

Awkward...XXXmas Time Is Here!

Awkward Pillow Talk ·

2024/12/17

It’s the most awkward time of the year, and Jason & Stephanie are back in full, unfiltered force! In this XXXmas-themed episode of Awkward Pillow Talk, they’re dishing on everything from unexpected holiday stress relief to Jason’s never-ending hernia surgery woes. Listen in as they rant about outrageous insurance bills, reveal their newly discovered neighbor drama, and share steamy behind-the-scenes stories—including that one spicy morning they spent with a unicorn.The holidays can be chaotic,

en

49:10

Awkward Stories: 3 Real-Life Soft Swap Adventures |...

Awkward Pillow Talk ·

2024/12/02

Welcome back to Awkward Pillow Talk! In this week’s episode, Jason and Stephanie open up about three of their most memorable—and hilariously awkward—soft swap experiences. From unexpected connections at a Jamaican resort to a high-spirited encounter that took an odd turn, they’re sharing it all.Episode Highlights: 1. The Canadian Connection at Hedo: Dive into their spontaneous soft swap with a mysterious Canadian couple at Hedonism resort. Hear how anxiety, misadventures, and a serendipitous meeting

en

32:20

Awkward...Help Stop Illiteracy In The Lifestyle + Our...

Awkward Pillow Talk ·

2024/11/21

🎙️ Awkward Pillow Talk is back with an all-new episode, and we’re tackling some very awkward truths about the lifestyle, the ups and downs of dating, and why Secrets Hideaway might not be for everyone. Plus, we dive into how a $100 drum set scored Stephanie her rockstar moment!🧐 P.S. If you’re a single guy in the lifestyle, this title might hit a little too close to home… because let’s be honest—many of y’all skip the descriptions. Don’t worry, we connect the dots for you in this episode. 😉👀

en

48:19

Awkward...Stephanie Confronts The Silent Partner (and...

Awkward Pillow Talk ·

2024/11/14

In this heartfelt episode of Awkward Pillow Talk, Jason and Stephanie delve into the challenges couples face when trying to deepen their connection and reignite intimacy. They share personal stories about overcoming societal expectations, improving communication, and taking those awkward first steps toward a more fulfilling relationship.Stephanie opens up about her journey from living in her head to embracing the moment, while Jason discusses the importance of mutual support and focusing on each

en

26:27

Awkward...Stephanie Takes Another Virginity (with...

Awkward Pillow Talk ·

2024/11/06

Welcome back to Awkward Pillow Talk with Jason and Stephanie! This week, we’re diving deep into the world of social anxiety, dating challenges, and breaking down barriers. We had the pleasure of sitting down with a courageous 20-year-old guest who opened up about his journey navigating relationships and overcoming personal hurdles.In this candid conversation, we explore: • 🗣️ The complexities of making meaningful connections in today’s world. • 🤝 Balancing respect and confidence when approaching

en

6:04

Awkward X History - Bill Clinton's Oral Office

Awkward Pillow Talk ·

2024/11/03

Get cozy, folks! In this steamy episode of Awkward X History, we’re diving deep into one of the most scandalous chapters of recent political history: the infamous affair between President Bill Clinton and Monica Lewinsky—also known as “The Oral Office Incident.”Join your host, Jason Class, as we set the scene in 1995—a time of booming economies, dial-up internet, and a seemingly more optimistic world. We’ll explore how a 22-year-old intern and the 49-year-old Commander-in-Chief became entangled in a

en

39:23

Awkward...Help! Jason Keeps Growing (+How We Wrangle...

Awkward Pillow Talk ·

2024/10/29

<p>Welcome to this special Halloween edition of <strong>Awkward Pillow Talk</strong> with Jason and Stephanie! 🖤🎃</p><p>This week, we're diving deep into the mystical world of <strong>unicorns</strong>—single women who join couples—and discussing <strong>unicorn safety</strong>, our personal experiences, and tips for navigating these unique relationships safely and enjoyably. 🦄✨</p><p>We also revisit our most popular episode on

en

43:32

Awkward... A XXX "Yes Day" (and Virgins 7, 8, 9, 10)

Awkward Pillow Talk ·

2024/10/21

In this episode of the Awkward Pillow Talk podcast, hosts Jason and Stephanie Class express their heartfelt gratitude to a growing international audience and discuss the exciting milestones their show has achieved. They highlight the importance of listener support, encouraging reviews, and explain how advertisements and partnerships, like the one with Nuud Pleasures (offering stackable discounts with the code “atalk”), help sustain the podcast.The couple delves into managing online interactions and

en

44:16

Awkward...Trust and The Big Dick Virgin

Awkward Pillow Talk ·

2024/10/17

Welcome back to another episode of the Awkward Pillow Talk podcast! In this candid conversation, Jason and Stephanie delve deep into the essential role of trust in their relationship, especially as they navigate unconventional experiences together. They discuss how eliminating teasing and practical jokes strengthened their bond, allowing for open communication and mutual understanding.But the episode takes an exciting turn as they share intriguing stories about their encounters with virgins numbered

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