Episodes
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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, so remember: a quick erotic rendezvous can go a long way toward keeping your sanity. Jason & Stephanie talk sex positivity through the festive season, how they’re managing family gatherings without losing that intimate spark, and why owning your truth (even if your neighbors find out!) is the best gift you can give yourself.
It’s funny, it’s real, and it’s oh-so-awkward—just the way you like it. Grab some eggnog, hit play, and join the fun as they unwrap holiday mishaps, share seasonal bedroom tips, and set the mood for a very merry XXXmas. Don’t miss out on the adult toy recommendations, aphrodisiac chocolate talk, and updates on their quest for new “friends.”
Happy holidays from Awkward Pillow Talk—stay weird, stay naughty, and stay tuned for more delightfully cringe-worthy episodes to come! And if you want a front-row seat to the mischief, be sure to check out their links for even more behind-the-scenes fun.
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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 led to an unforgettable experience.
2. Electric Moments with the Violet Wand: Join them as they recount meeting a captivating couple during a BDSM class. Explore how a violet wand sparked not just electricity but also an intense connection and one of Stephanie’s most powerful orgasms.
3. The Northern Virginia Surprise: Discover what happens when a planned meetup turns into an awkward encounter involving homemade weed and an unexpected revelation that brings the fun to a screeching halt.
Plus, they discuss:
• The challenges of content creation and dealing with anxiety.
• Exciting updates about their TikTok shop featuring their favorite self-care products.
• How you can support them on Fansly and gain access to exclusive content.
Don’t miss this episode filled with laughter, candid moments, and the genuine awkwardness that makes Jason and Stephanie so relatable.
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• 🌐 All Our Links: VirginitySnatchers.com
• 🎥 TikTok Shop: @awkwardpillowtalk
• 📸 Fansly: Support us and join the contest!
• 🛍 Self-Care Favorites: Find our recommended products on our TikTok shop.
Connect with Us:
• TikTok: @awkwardpillowtalk
• Twitter: @awkwardpillowtlk
• Instagram: @awkwardpillowtalk
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Enjoyed the episode? Like, subscribe, and leave a review! Your support helps us continue sharing these awkward yet amazing stories.
Support this podcast at — https://redcircle.com/awkward/donations -
Missing episodes?
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🎙️ 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. 😉
👀 What We Cover in This Episode:
• 🎵 Stephanie’s unexpected knack for drumming and how music is bringing us even closer.
• 🫠 Awkward struggles navigating lifestyle apps and why single men need to actually read directions.
• 🏩 Our brutally honest review of Secrets Hideaway: from room fails to the hot tub incident that made us say, “never again (maybe).”
• 🤔 Why patience, respect, and following instructions are essential for connecting with creators like us.
💬 Got questions, comments, or stories to share? Email us at [email protected] or visit VirginitySnatchers.com to find all our links!
🌟 Don’t forget to:
• Like 👍
• Comment 💬
• Subscribe ✅
• Share with a friend! 📤
✨ Support our work and dreams by visiting our site, checking out our wish lists, and leaving reviews on your favorite podcast platforms.
#AwkwardPillowTalk #SecretsHideaway #LifestylePodcast #SwingerLife #HonestReview #SingleMenProblems #ReadTheDescription #CoupleGoals #PodcastEpisode #AdultContentCreator #RelationshipTalk #AwkwardMoments #SecretsReview #VirginitySnatchers #PodcastRecommendations #MarriageGoals
🎧 Catch us on all major podcast platforms and YouTube! Hit play, and let’s get awkward together!
Support this podcast at — https://redcircle.com/awkward/donations -
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 other’s needs. Together, they offer practical advice for couples looking to push their boundaries just a little bit and explore new facets of their relationship.
They also share their experience with the Motorbunny, a device that has added a new dimension to their intimacy and could do the same for you. Interested in discovering more? Visit virginitysnatchers.com to purchase a Motorbunny through their affiliate link.
Join them for an honest and encouraging conversation that might just inspire you to take that leap with your best friend.
Support this podcast at — https://redcircle.com/awkward/donations -
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 new relationships.
• 🌟 The pressures society places on intimacy and how to handle them.
• 🎥 Behind-the-scenes insights into our experiences with creating open and honest content.
• 💬 Tips for overcoming social anxiety and stepping out of your comfort zone.
We also reflect on our own growth as we kick off what we’re calling Season 3! From coordinating with past guests to planning exciting new content, we’re thrilled to share this journey with you.
Whether you’re dealing with social anxiety, curious about modern dating, or just in need of some real talk, this episode is packed with insights and stories that you won’t want to miss.
Tune in now and join the conversation!
🎧 Listen on your favorite podcast platform.
VirginitySnatchers.com
#AwkwardPillowTalk #Podcast #NewEpisode #SocialAnxiety #Dating #Relationships #RealTalk #Season3 #BehindTheScenes
Support this podcast at — https://redcircle.com/awkward/donations -
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 relationship that not only rocked the White House but also left a permanent mark on the American political landscape.
From secret encounters in the Oval Office to the infamous blue dress, we’re unraveling the details of this intense and emotionally charged liaison. We’ll delve into how the scandal unfolded, the media frenzy that ensued, and its lasting impact on both Bill and Monica.
As we head towards another election, we’ll reflect on the lessons learned and ponder whether history has a funny way of repeating itself. Don’t miss this deep dive into awkward sex history that’s both enlightening and entertaining.
Tune in now on virginitysnatchers.com.
Keywords & Hashtags:
#Election2024 #PoliticalScandal #MonicaLewinsky #BillClinton #OralOffice #AwkwardSexHistory #PresidentialAffair #Impeachment #HistoryRepeats #Vote #WhiteHouse #1990sPolitics #Scandal #PoliticalHistory #USPolitics #BlueDress #LindaTripp #InternAffair #PoliticalLessons #JasonClass #VirginitySnatchers
Support this podcast at — https://redcircle.com/awkward/donations -
<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 the <strong>XXX Yes Day</strong>, clarifying its importance in understanding and fulfilling your partner's needs. If you haven't listened to it yet, now's the perfect time! 🔥</p>
<p><strong>Exciting News!</strong> We're gaining momentum on TikTok and are thrilled to announce <strong>TikTok Tuesdays</strong>! Join us every Tuesday at 10 PM EST on TikTok <a href="https://www.tiktok.com/@awkwardpillowtalk">@AwkwardPillowTalk</a> for live discussions, Q&A sessions, and more. We love interacting with you all, so bring your questions and let's chat! 📱🎥</p>
<p>Jason shares his adventures (and misadventures) testing out male pleasure products from <strong>Brazzers Toys</strong>, <strong>The Handy</strong>, and <strong>Kiiroo</strong>. Find out which ones hit the spot and which ones... left him in a tight situation! 😳🔞</p>
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<p><strong>Huge thanks to our amazing sponsors:</strong></p>
<ul>
<li><strong>Sheets of San Francisco</strong>: <a href="https://sheetsofsanfrancisco.com/">Website</a></li>
<li><strong>Brazzers Toys</strong>: <a href="https://brazzers.com/toys">Website</a></li>
<li><strong>The Handy</strong>: <a href="https://www.thehandy.com/">Website</a></li>
<li><strong>Kiiroo</strong>: <a href="https://www.kiiroo.com/">Website</a></li>
<li><strong>Fyr Body</strong>: <a href="https://www.fyrbody.com/">Website</a></li>
</ul>
<p>Your support keeps the fun going! 🙌</p>
<hr>
<p>👉 <strong>Check out our sponsors and affiliates:</strong> <a href="https://virginitysnatchers.com/">VirginitySnatchers.com</a></p>
<p>👉 <strong>Support Steph's adult content:</strong> <a href="https://onlyfans.com/stephanieclassx">OnlyFans</a></p>
<hr>
<p><strong>Don't forget to:</strong></p>
<ul>
<li><strong>Leave us a review</strong> ⭐⭐⭐⭐⭐</li>
<li><strong>Subscribe</strong> so you never miss an episode</li>
<li><strong>Share</strong> with friends who might enjoy our content</li>
</ul>
<hr>
<p><strong>Connect with us:</strong></p>
<ul>
<li><strong>Email:</strong> <a href="mailto:[email protected]">[email protected]</a></li>
<li><strong>TikTok:</strong> <a href="https://www.tiktok.com/@awkwardpillowtalk">@AwkwardPillowTalk</a> and <a href="https://www.tiktok.com/@stephanieclassx">@StephanieClassX</a></li>
<li><strong>Website:</strong> <a href="https://awkwardpillowtalk.com/">AwkwardPillowTalk.com</a></li>
</ul>
<hr>
<p><strong>Join us on TikTok Tuesdays at 10 PM EST!</strong></p>
<hr>
<p><strong>Hashtags:</strong></p>
<p>#AwkwardPillowTalk #Podcast #Unicorns #UnicornSafety #XXXYesDay #HalloweenSpecial #TikTokTuesdays #BrazzersToys #TheHandy #Kiiroo #FyrBody #SheetsOfSanFrancisco #AdultContent #SexPositive #RelationshipAdvice #CouplesPodcast #NSFW</p>
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<p><strong>Disclaimer:</strong> This podcast contains adult content and is intended for mature audiences. Listener discretion is advised.</p>
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<p><em>Thanks for tuning in! We appreciate your support and can't wait to connect with you on TikTok Tuesdays. Stay awkward and keep the conversations going! 💕</em></p>
Support this podcast at — https://redcircle.com/awkward/donations -
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 the best ways for fans to connect with Stephanie respectfully through her official platforms. They emphasize the significance of boundaries, fair communication, and the importance of supporting content creators by subscribing to their pages.
Jason and Stephanie introduce a relationship exercise inspired by the concept of a “Yes Day,” aiming to enhance trust and communication between partners. They share personal anecdotes on how this practice has positively impacted their own relationship, helping them navigate decision paralysis, anxiety, and self-care routines. The discussion includes practical advice on setting boundaries, expressing needs, and the benefits of mutual support in a partnership.
They also touch upon their experiences in helping individuals overcome personal hurdles, discussing topics like anxiety-related challenges and the importance of seeking professional assistance when necessary. The episode wraps up with reminders to visit their website, virginitysnatchers.com, and to follow Stephanie on various platforms for exclusive content and updates.
Join Jason and Stephanie for an insightful conversation filled with personal stories, relationship tips, and a glimpse into how open communication can strengthen bonds.
Support this podcast at — https://redcircle.com/awkward/donations -
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 2 through 6, including the unforgettable tale of the “Big Dick Virgin.” From unexpected challenges to humorous moments, they offer an honest look into their journey of helping others embrace new experiences.
Tune in to hear about:
• The unspoken rules that have solidified their trust.
• Behind-the-scenes stories of working with nervous newcomers.
• The adventures and lessons learned from their unique experiences.
• Insights into balancing personal growth with relationship dynamics.
Whether you’re curious about building deeper trust in your relationship or interested in their entertaining anecdotes, this episode promises a mix of humor, honesty, and heartfelt advice.
Check out more of their content and exclusive videos at virginitysnatchers.com
Join the conversation and don’t forget to like, subscribe, and share!
Support this podcast at — https://redcircle.com/awkward/donations -
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 Edward VIII took ‘ruling from the throne’ to a whole new level. Get ready for some seriously awkward royal history that’s equal parts jaw-dropping and hilarious!
VirginitySnatchers.com
Support this podcast at — https://redcircle.com/awkward/donations -
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 truth behind the headlines.
Don’t forget to like, comment, and subscribe for more deep dives into celebrity controversies and awkward moments from history!
#Diddy #SeanCombs #Controversies #CelebrityScandals #MusicIndustry #Lawsuits #HipHop #freakOff #PuffDaddy #Swingers
Support this podcast at — https://redcircle.com/awkward/donations -
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.
The trio discusses everything from navigating the lifestyle community to what it really means to be comfortable in your own skin. Amy shares stories of her modeling days and why being shamelessly open about sexuality is empowering. If you’ve ever wondered what it’s like to take on the sex world with confidence, this episode is packed with laughs, honesty, and a few surprises.
And of course, don’t forget to check out Jason and Stephanie’s latest virginity-snatching adventures on virginitysnatchers.com and explore more about Amy’s work on amytaylornyc.com!
Subscribe, like, and stay tuned for more awkward, honest, and hot content!
Support this podcast at — https://redcircle.com/awkward/donations -
In this episode of Awkward X History, we dive into the world of silent film star Charlie Chaplin—not just for his comedic genius, but for one of his lesser-known quirks: his serious thing for feet. From the silver screen to the bedroom, Chaplin’s love of all things toes shaped more than just his films. Join us as we explore how even the greats had their strange fascinations and how Chaplin’s foot fetish became a part of his awkward legacy. This isn’t your typical history lesson—it’s the awkward, weird, and oddly fascinating side of one of Hollywood’s biggest icons!
#AwkwardXHistory #CharlieChaplin #FootFetish #WeirdHistory #HollywoodLegends #ComedicGenius #AwkwardFacts #SilentFilmStar
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In this episode of Awkward Pillow Talk, Jason and Stephanie Class sit down with relationship and intimacy coach Brianna Carey for a candid and insightful conversation about the often-overlooked importance of communication in relationships. Together, they dive into the real-life challenges of parenting, balancing intimacy, and navigating alternative lifestyles. Brianna offers practical advice on how couples can reconnect, especially postpartum, and highlights the value of prioritizing the relationship despite the demands of family life. They also explore the pressure of societal gender roles and the need to create safe spaces for honest and open dialogue. Throughout the episode, Jason, Stephanie, and Brianna stress the importance of understanding each other’s communication styles and using curiosity as a tool for deepening connection.
#AwkwardPillowTalk #RelationshipAdvice #IntimacyCoach #ParentingAndPartnership #CommunicationInMarriage #JasonAndStephanieClass #SexAndRelationships
Support this podcast at — https://redcircle.com/awkward/donations -
In this wild episode of Awkward Pillow Talk, Jason and Stephanie Class dive deep into the most outrageous and awkward topics yet! From sharing their spicy group adventures to answering the most daring and NSFW TikTok questions, nothing is off-limits in this hilarious, uncensored conversation. Whether it’s gangbangs, awkward sex games, or tackling those viral TikTok inquiries, Jason and Stephanie aren’t holding back.
Curious about how swinging strengthened their relationship? Want to know how they handle those awkward, but oh-so-common, bedroom questions? They’ve got all the answers and a lot of laughs along the way. Plus, they spill the details on their infamous “group project” (aka gangbang) and reveal some of their favorite kinky games!
Tune in for unfiltered fun, awkward moments, and honest advice on love, sex, and everything in between!
#AwkwardPillowTalk #GangbangStories #TikTokQuestions #SexAndAnxiety #GroupSex #AwkwardPillowTalkPodcast #JasonAndStephanieClass #Swingers #NSFW
Support this podcast at — https://redcircle.com/awkward/donations -
Get ready for another awkward dive into history with ‘Awkward Pillow Talk’ as we explore the surprisingly steamy side of literary legend James Joyce. Known for his masterpiece Ulysses, Joyce also had a knack for writing some very explicit love letters to his wife—like, awkwardly explicit. In this episode, we uncover the hilariously intimate side of this famous author that’s as weird as it is fascinating. Perfect for anyone who loves cringeworthy moments, unexpected kinks, and historical figures who were definitely into some… weird stuff. You won’t read Ulysses the same way again(or ever?)!
VirginitySnatchers.com
Support this podcast at — https://redcircle.com/awkward/donations -
This conversation delves into the complex and often awkward personal life of Marvin Gaye, exploring his voyeuristic tendencies and emotional struggles that shaped his music. It highlights how his kinks and relationships influenced his iconic songs, revealing a deeper layer to the man behind the smooth vocals.
Support this podcast at — https://redcircle.com/awkward/donations -
In this explicit episode of Awkward Pillow Talk, Jason and Stephanie Class delve into their personal experiences with intimacy, body positivity, and the swinger lifestyle. They share candid stories about their challenges with lingerie, their journey of weight loss, and the dynamics of finding compatible couples in the swinging community. The conversation also touches on their collaborations with brands and the importance of mutual respect and understanding in intimate relationships. With humor and honesty, they explore the complexities of their sexual adventures and the lessons learned along the way.
AwkwardTalk.com
Support Small Businesses and Buy from Selfcare.Lingerie on IG
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Support this podcast at — https://redcircle.com/awkward/donations -
In this episode, Stephanie and Jason Class discuss their experiences with adult content creation, focusing on the hot wife lifestyle and the journey of filming virgin experiences. The conversation explores the importance of sexual education, the historical context of sexuality, and the challenges faced in the adult industry. Stephanie shares personal anecdotes, insights into the dynamics of relationships, and the evolution of their content creation process, emphasizing the need for clear communication and consent in their work.
Support this podcast at — https://redcircle.com/awkward/donations -
Dr. Stephanie Snyder and Jason and Stephanie Class discuss the importance of communication in relationships, particularly during pregnancy. They share their experiences and strategies for maintaining physical and emotional connection during this time. They also touch on the significance of comprehension in communication and the need to clarify and understand each other's perspectives. Dr. Snyder talks about her podcast, 'Cutting Through the Bullshit,' where she helps people overcome overthinking and take action towards their goals.
Listen to Dr Stephanie Snyders Podcast Here - https://podcasts.apple.com/us/podcast/cutting-through-the-bullsh-t-with-dr-stephanie-snyder/id1438668175
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