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...

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...

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...

Welcome to this special Halloween edition of Awkward Pillow Talk with Jason and Stephanie! 🖤🎃 We’re calling it our “Halloween special” as a subtle joke—both of us are wearing black, setting a fun and slightly spooky mood for this episode. This week, we’re diving deep into the mystical world of unicorns—single women who join couples—and discussing unicorn safety, our personal experiences, and tips for navigating these unique relationships safely and enjoyably. 🦄✨ We also revisit our most...

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...

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...

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....

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...

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...

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...

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...

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...

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...

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 Advertising Inquiries: https://redcircle.com/brands Privacy & Opt-Out: https://redcircle.com/privacy

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...

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...

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 B******t,' where she helps people overcome...

In this episode, we dive into a surprising and empowering story from none other than Friends star Lisa Kudrow! Known for her role as the quirky and lovable Phoebe Buffay, Lisa has shared an interesting piece of her personal life that many fans might not know. Unlike most Hollywood stars, Lisa waited until marriage to lose her virginity—and her reasons for doing so are as refreshingly honest as her sense of humor. Join us as we explore Lisa’s journey, her decision to wait, and how it shaped...

In today’s episode, we take a deep dive into the scandalous and often misunderstood life of Catherine the Great, one of history’s most powerful and legendary rulers. While Catherine was known for her incredible political prowess and transforming Russia into a global power, her personal life has been the subject of wild rumors and controversy—especially regarding her love life. From her infamous affairs with younger men to the myths about her unconventional relationships, we’ll unravel the...

Summary In this conversation, Jason and Stephanie Class share their personal journey of weight loss and transformation, discussing their struggles with weight, the various methods they tried, and their eventual success with semaglutide. They emphasize the importance of finding the right solutions for individual needs and the impact of community support in achieving health goals. Their candid discussion highlights the emotional and physical challenges faced during their journey, as well as...

In this episode of Awkward Pillow Talk, Jason and Stephanie Class share their experiences at Desire Pearl, a lifestyle resort in Mexico, during the COVID pandemic. They discuss the challenges of traveling during this time, including anxiety about health and safety, and the unique atmosphere of the resort. The couple reflects on their dining experiences, the luxurious mansion they stayed in, and the personal service they received. They also touch on their journey into content creation and the...

In this episode of Awkward Pillow Talk, Jason and Stephanie discuss their experiences with using marijuana or cannabis products during sex. They talk about the stigma surrounding weed and their journey in exploring its use in their relationship. They share their thoughts on different strains and products they have tried, including vapes, gummies, and joints. They highlight the positive effects of cannabis on their mood, relaxation, and sexual experiences. They also mention a company called...

Audio Only - In this no-holds-barred episode, Jason and Stephanie dive deep into the raw, unfiltered drama that’s been shaking up their lives both online and off. After four attempts to record, we’re finally dishing out the juicy details on why we went a full week without pay from OnlyFans. Get ready for a rollercoaster of emotions as we reveal how hacked accounts, unexpected chargebacks, and platform policies have put our livelihood on the line—right before a holiday weekend. 🏠 But that’s...

In this conversation, Jason and Stephanie Class discuss their experience with hypnotherapy and the power of the mind-body connection. They share how they discovered that the color black, which they initially perceived as negative, actually symbolized significant life change. The conversation also explores the importance of imagination and visualization in creating transformation. They discuss their journey of self-discovery and the interconnectedness of their relationships. The conversation...