Awkward Pillow Talk
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 about it! Visit us at AwkwardTalk.com’
Episodes
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.com
Support this podcast at — https://redcircle.com/awkward/donations
🎙️ Inside Hedonism II: Lifestyle, Swingers, and Travel Secrets with Author Chris Santilli | Awkward Pillow Talk Podcast
In 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 h...
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 chang...
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 censorshi...
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_free
X (Twitter)
🔹 @mi...
Awkward… Initiation - A Real Couple’s First Time Swapping with Jason and Stephanie
🔥 Watch the Full Video Now ➡️ VirginitySnatchers.com
In 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 Thi...
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...
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 s...
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 s...
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 Hedo...
🎙️ 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 descrip...
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 ...
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 i...
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-yea...
<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 enj...
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...
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 t...
You thought the British monarchy was all about stiff upper lips and tea? Think again! In this episode of Awkward Sex History, we dive into the scandalous love life of King Edward VIII, the royal who gave up the throne for love… and had quite the throne of his own! Discover the outrageous tale behind his infamous sex chair – a custom-built contraption fit for a king’s wildest fantasies. From secret mistresses to royal romps, King Ed...
In this episode, we dive deep into the controversies surrounding Sean “Diddy” Combs. From his rise to fame as a music mogul to the scandals and lawsuits that have recently surfaced, things have taken a dark turn for Diddy. We explore the timeline of events, including the jaw-dropping accusations and how they’ve impacted his legacy. Is this the fall of one of hip-hop’s biggest icons? Watch as we break it all down and reveal the trut...
In this episode of Awkward Pillow Talk, Jason and Stephanie Class hunker down as Hurricane Milton brushes past Florida, but that doesn’t stop them from bringing the heat! They’re joined by the stunning Amy Taylor, a Playboy and Maxim model, who dives deep into some steamy and insightful conversation. From breaking down barriers around sex and body confidence to sharing her journey in the adult industry, Amy holds nothing back.
T...
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