Awkward Pillow Talk
Episodes
Awkward Hotwife - A True Story from a Real Swinger Wife- The Hotel Game - StephanieClass
30 Oct 2025
Contributed by Lukas
Awkward Hotwife: A True Story from a Real Swinger WifeShe looks like your everyday mom, teacher, or next-door neighbor—but beneath that familiar sur...
Awkward...First Time Jitters
16 Sep 2025
Contributed by Lukas
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 lifest...
Awkward…Data-Driven Boners (featuring FirmTech CEO Dr. Elliot Justin) + Virgins 22 & 23
04 Sep 2025
Contributed by Lukas
Awkward…Data-Driven Boners (featuring FirmTech CEO Dr. Elliot Justin) + Virgins 22 & 23In this episode of Awkward Pillow Talk, Jason and Stephan...
Awkward...Nude Beach Review
11 Jul 2025
Contributed by Lukas
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 c...
Awkward...Update 05/13/25
13 May 2025
Contributed by Lukas
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 ba...
Awkward...Stories about Hedo with Chris Santilli
25 Mar 2025
Contributed by Lukas
🎙️ Inside Hedonism II: Lifestyle, Swingers, and Travel Secrets with Author Chris Santilli | Awkward Pillow Talk PodcastIn this episode of Awkward...
Awkward… A March Festivus (The Airing of Grievances)
13 Mar 2025
Contributed by Lukas
Awkward Pillow Talk – Awkward… A March Festivus (The Airing of Grievances)Welcome back to Awkward Pillow Talk! This week, Jason and Stephanie are ...
Awkward...Penguins and Pocket Pussies
03 Mar 2025
Contributed by Lukas
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 tri...
Awkward...and Miss Behavin
14 Feb 2025
Contributed by Lukas
We had an absolute blast chatting with @missbehavinxoxo—hilarious, sexy, and completely unfiltered! From wild industry stories to balancing life as ...
Awkward...Initiation - A Real Couples First Time Swapping With Jason and Stephanie
03 Feb 2025
Contributed by Lukas
Awkward… Initiation - A Real Couple’s First Time Swapping with Jason and Stephanie🔥 Watch the Full Video Now ➡️ VirginitySnatchers.comIn th...
Awkward...From Vanilla to...Spicy?
16 Jan 2025
Contributed by Lukas
Ever wondered how a shy, naïve, barely-ever-touched-a-vibrator girl transforms into a full-on, sex-positive content creator? Look no further—Stepha...
Awkward... 2025 The Year Of The Ho
02 Jan 2025
Contributed by Lukas
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 neighborhoo...
Awkward...XXXmas Time Is Here!
17 Dec 2024
Contributed by Lukas
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 Pillo...
Awkward Stories: 3 Real-Life Soft Swap Adventures | Awkward Pillow Talk
02 Dec 2024
Contributed by Lukas
Welcome back to Awkward Pillow Talk! In this week’s episode, Jason and Stephanie open up about three of their most memorable—and hilariously awkwa...
Awkward...Help Stop Illiteracy In The Lifestyle + Our Review of Secrets Hideaway
21 Nov 2024
Contributed by Lukas
🎙️ 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 d...
Awkward...Stephanie Confronts The Silent Partner (and MOTORBUNNY CMO CRAIG MEWBOURNE!)
14 Nov 2024
Contributed by Lukas
In this heartfelt episode of Awkward Pillow Talk, Jason and Stephanie delve into the challenges couples face when trying to deepen their connection an...
Awkward...Stephanie Takes Another Virginity (with Special Guest Virgin 21)
06 Nov 2024
Contributed by Lukas
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 ...
Awkward X History - Bill Clinton's Oral Office
03 Nov 2024
Contributed by Lukas
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...
Awkward...Help! Jason Keeps Growing (+How We Wrangle Unicorns)
29 Oct 2024
Contributed by Lukas
<p>Welcome to this special Halloween edition of <strong>Awkward Pillow Talk</strong> with Jason and Stephanie! 🖤🎃</p><...
Awkward... A XXX "Yes Day" (and Virgins 7, 8, 9, 10)
21 Oct 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, hosts Jason and Stephanie Class express their heartfelt gratitude to a growing international audie...
Awkward...Trust and The Big Dick Virgin
17 Oct 2024
Contributed by Lukas
Welcome back to another episode of the Awkward Pillow Talk podcast! In this candid conversation, Jason and Stephanie delve deep into the essential rol...
Awkward X History | The Erotic Furniture of King Edward VII
13 Oct 2024
Contributed by Lukas
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 scandal...
Awkward X History | Diddy Do It? (A great opportunity to discuss consent)
11 Oct 2024
Contributed by Lukas
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 la...
Awkward...The Hurricane Hits, But Amy Taylor Brings The Heat!
09 Oct 2024
Contributed by Lukas
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 f...
Awkward X History | Charlie Chaplin was a Foot Guy
06 Oct 2024
Contributed by Lukas
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...
Awkward...You Can Bang, But Can You Communicate? (with Special Guest Brianna Carey)
05 Oct 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class sit down with relationship and intimacy coach Brianna Carey for a candid and insight...
Awkward...Gangbangs, Sex Games, and Tiktok Questions (Answered!)
03 Oct 2024
Contributed by Lukas
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 s...
Awkward X History | James Joyce Was A Fart Sniffer
30 Sep 2024
Contributed by Lukas
Get ready for another awkward dive into history with ‘Awkward Pillow Talk’ as we explore the surprisingly steamy side of literary legend James Joy...
Awkward x History | Was Marvin Gaye The Original "Freak-Off" Director?
24 Sep 2024
Contributed by Lukas
This conversation delves into the complex and often awkward personal life of Marvin Gaye, exploring his voyeuristic tendencies and emotional struggles...
Awkward...The Perfect Full-Swap Couple
23 Sep 2024
Contributed by Lukas
In this explicit episode of Awkward Pillow Talk, Jason and Stephanie Class delve into their personal experiences with intimacy, body positivity, and t...
Awkward...Stephanie's First Time Being Shared As A Hotwife
19 Sep 2024
Contributed by Lukas
In this episode, Stephanie and Jason Class discuss their experiences with adult content creation, focusing on the hot wife lifestyle and the journey o...
Awkward...Cutting Through The BS (with Dr.Stephanie Snyder)
18 Sep 2024
Contributed by Lukas
Dr. Stephanie Snyder and Jason and Stephanie Class discuss the importance of communication in relationships, particularly during pregnancy. They share...
Awkward X History | Lisa Kudrow's Virginity | With Stephanie Class
18 Sep 2024
Contributed by Lukas
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 lo...
Awkward X History | Catherine The Great (kind of a ho...)
17 Sep 2024
Contributed by Lukas
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 an...
Awkward...You Lost 50lb By Being Lazy (FYRBody.com/AwkwardTalk)
14 Sep 2024
Contributed by Lukas
SummaryIn this conversation, Jason and Stephanie Class share their personal journey of weight loss and transformation, discussing their struggles with...
Awkward...Our Mexican Butler Thinks We Are Idiots
12 Sep 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class share their experiences at Desire Pearl, a lifestyle resort in Mexico, during the CO...
Awkward...Stephanie Class is your Nuud (Legal) Weed Dealer
11 Sep 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie discuss their experiences with using marijuana or cannabis products during sex. They talk ...
Awkward...Unsexy Drama (That made us have more SEX)
04 Sep 2024
Contributed by Lukas
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 o...
Awkward...You Hypnotized Your Friend
30 Aug 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class discuss their experience with hypnotherapy and the power of the mind-body connection. They share how t...
Awkward...When The Sheets Aren't The Only Thing Getting Wet
27 Aug 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie discuss their current life changes and the unexpected drama they are facing. They talk abo...
Awkward...Your New Role Model Owns A Brothel (with Mistress Bella Cummins)
20 Aug 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview Bella Cummins, America's Longest Serving Brothel Madam. Th...
Awkward...Let Me Take A Pikachu (with Timothy Baxter)
13 Aug 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class talk to Tim Baxter, a licensed clinical professional counselor and sex therapist. Th...
Awkward...You Got Catfished By A Lady With Pink Hair (with special guest Patsy Roach)
06 Aug 2024
Contributed by Lukas
Patsy Roach, also known as Suzanne Sugarbaker, shares her experiences as a scammer therapist and her journey in exposing scammers on TikTok. She start...
Awkward...You Thought My Sex Life Was Your Business (Featuring SexxxySoccerMom)
31 Jul 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class interview SexxxySoccerMom, a fellow hot wife, about their experiences in the hot wife lifestyle. They ...
Awkward...The Congress of Virginity Snatchers (With AsianVixen4U)
24 Jul 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview their guest, June (Asian Vixen for You), who also takes virgin...
Awkward...Dirty 30's Birthday Sex
23 Jul 2024
Contributed by Lukas
Jason and Stephanie Class discuss their plans for Stephanie's Birthday...which is nothing. They also discuss the one thing Jason asks for every ye...
Awkward...Your Favorite Pornstar is in Your Bed (With your Wife!)
17 Jul 2024
Contributed by Lukas
In this conversation, Stephanie Class, Candi_Canes, and Suck-A-Saurus discuss various topics related to watching porn and the experiences of sex worke...
Awkward...Your Post-Nut Clarity Is Harshing My Vibe
12 Jul 2024
Contributed by Lukas
n this conversation, Jason and Stephanie discuss their recent experiences with finding and engaging with virgins for their adult content. They talk ab...
Awkward...The Dinosaur and The Virgin Slayer
07 Jul 2024
Contributed by Lukas
Stephanie Class and Suck-A-Saurus discuss Stephanie's experience taking men's virginities and the impact it has on their lives. They talk abou...
Awkward...It's Not All Sunshine And Orgies
24 Jun 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie discuss their recent struggles with their OnlyFans account and other social media platform...
Awkward...Do Aussies "Do It" Kangaroo Style?
18 Jun 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class interview Rachel, a new creator on OnlyFans. They discuss Rachel's journey as a ...
Awkward...Trauma Witch
17 Jun 2024
Contributed by Lukas
In this episode, Jason and Stephanie Class discuss anxiety and unconventional approaches to healing. They interview Bryn, a trauma-informed witch and ...
Awkward...Your Coochie Hurts
09 Jun 2024
Contributed by Lukas
In this episode, Jason and Stephanie Class interview Naomi Harris, a practitioner who works with women who have sexual pain and issues. They discuss t...
Awkward...You Hired A Sex Coach
05 Jun 2024
Contributed by Lukas
Summary In this episode of Awkward Pillow Talk, Jason and Stephanie discuss their plans for the podcast and their decision to slow down the release o...
Awkward...Erotic Hypnosis with Mark Kemp
30 May 2024
Contributed by Lukas
In this episode, Mark Kemp, a certified hypnotherapist, discusses erotic hypnosis and its practical applications. He shares his personal journey of us...
Awkward...That Shy Girl Is A Freak (in the sheets)
26 May 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk Podcast, Jason and Stephanie Class interview Fiona Cutts, a sex coach for shy girls. Fiona shares her own j...
Awkward...Strip Club Grilled Cheese with Nicole Pearl
24 May 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview Nicole Pearl, a content creator on OnlyFans, LoyalFans, and Ma...
Awkward...You Didn't Understand The True Meaning Of Memorial Day
23 May 2024
Contributed by Lukas
A break from the norm, Jason and Stephanie open up about Memorial Day, discussing Jason's Brother who was killed in Iraq, and what it means to be ...
Awkward...and Unapologetic
22 May 2024
Contributed by Lukas
Jason and Stephanie Class, along Jess Marie (Unapologetically Overcoming Podcast) discuss their experiences in the adult industry and their approach...
Awkward...You Need A Swing Coach But You Don't Play Baseball
20 May 2024
Contributed by Lukas
with The Confident Swinger - Jo Leavitt In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview Jo Leavitt, a lifestyl...
Awkward...Your Sex Shame is Messing With Your Business "Game"
18 May 2024
Contributed by Lukas
The conversation Between Jason and Stephanie Class, and Sarah Jefferson explores the importance of ethics and values in the digital marketing industry...
Awkward...You Have A Voice For Porn (With Karl Wilder)
17 May 2024
Contributed by Lukas
in this conversation, Jason and Stephanie Class chat with Karl Wilder about his experiences in the adult film industry including voicing adult films a...
Awkward...You Can't Make Your Wife Cum (with Mangala Holland)
16 May 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview Mangala, an expert in female pleasure and orgasms. They discus...
Awkward...Confronting My Husbands Online Crush (with Suck.a.Saurus)
14 May 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class interview Suckasaurus, a favorite creator of theirs. They express their ...
Awkward...Naked Pictures Of Your Friends
12 May 2024
Contributed by Lukas
Jason and Stephanie Class discuss their decision to come out as independent creators and their plans to collaborate with others in the industry. The...
Awkward...How to tell your mom you're a Porn Star.
09 May 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class discuss their journey of embracing their sexuality and opening up about their work on OnlyFans. They s...
Awkward...Mermaid BJ's with Ask_Ashley479
08 May 2024
Contributed by Lukas
Ashley, a TikTok creator with half a million followers, shares her journey into the world of OnlyFans and the challenges she faced along the way. She ...
Awkward...with Serapheeds
08 May 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class talk with Serapheeds about their experiences with explicit content and being banned on various platfor...
Awkward...When Your Mom Tells Facebook You're a Swinger
07 May 2024
Contributed by Lukas
With ThatHotCoupleInGA In this episode, Jason and Stephanie Class interview Russ and Ashley from ThatHotCoupleinGA. They discuss how they were outed ...
Awkward...with Hedo Joe
03 May 2024
Contributed by Lukas
Joe Canino shares his experience and insights about Hedonism II in Jamaica, a popular vacation spot for those in the lifestyle. He started a group to ...
Awkward...Swinger Dates
01 May 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class discuss the importance of safety when meeting new people in the lifestyle. They shar...
Awkward...You want to go to a Glory Hole!
29 Apr 2024
Contributed by Lukas
Jason and Stephanie Class discuss their experiences with glory holes, including their visits to two different parties. They share their initial miscon...
Awkward...Autistic Pornstars (with Sam Sundius)
26 Apr 2024
Contributed by Lukas
In this Awkward conversation, Jason and Stephanie Class talk with Sam Sundius about neurodivergence, and the overlap between autism and sex work. They...
Awkward...with Dr.Nic Natale
26 Apr 2024
Contributed by Lukas
In this episode of Awkward Pillow Talk, Jason and Stephanie Class interview Dr. Nic, a therapist and hypnotherapist who specializes in helping people ...
Awkward...with Nita Marie
25 Apr 2024
Contributed by Lukas
In this episode, Jason and Stephanie Class engage in a riveting conversation with Nita Marie, an author, coach, OnlyFans creator, and advocate for wom...
Awkward...Introducing Your Spouse To Porn
24 Apr 2024
Contributed by Lukas
In this episode of the Awkward Pillow Talk podcast, Jason and Stephanie Class discuss their experiences with pornography and how it has influenced the...
Awkward...with Claire Doré
23 Apr 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class speak with Claire Doré, a relationship, dating, and sex coach. They discuss the importance of deep co...
Awkward...with Staja Kaye
23 Apr 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class talk to Staja Kaye, who has experience with kinks and fetishes. They discuss the unique and sometimes ...
Awkward Pillow Talk - Stories - An Unexpected "Happy Ending"
21 Apr 2024
Contributed by Lukas
Jason and Stephanie share their experience of going on a vacation to Desire Pearl in Mexico during the COVID-19 pandemic. They talk about their excite...
Awkward Pillow Talk - Stories - Gang Bang Thursday
19 Apr 2024
Contributed by Lukas
This story is an excerpt from another one of our podcasts, describing our first experience at a lifestyle club. Jason and Stephanie decide to explore...
Awkward Pillow Talk - Stories - Awkward Collab
19 Apr 2024
Contributed by Lukas
In this conversation, Jason and Stephanie discuss their experience with a female photo shoot that turned out to be awkward. They had planned to recrea...
Awkward Pillow Talk - Stories - Pandora's Forest
19 Apr 2024
Contributed by Lukas
Summary Jason and Stephanie share their experience at Pandora's Forest, a swinger resort in Tennessee. They talk about their first time being nak...
Awkward...Making Sex A Priority
19 Apr 2024
Contributed by Lukas
The conversation revolves around the importance of keeping sex a priority in a relationship. The hosts discuss their experiences with maintaining inti...
Awkward Pillow Talk - Stories - Belly Flops in the Nude Pool
18 Apr 2024
Contributed by Lukas
Stephanie and Jason discuss one of their more memorable, Non-Sexual, experiences at Hedonism II in Jamaica. The hosts share their experiences at the r...
Awkward Pillow Talk - Stories - Our Worst Hook-Up
16 Apr 2024
Contributed by Lukas
Jason and Stephanie their first hand experiences in Awkward Pillow Talk Stories. In this episode - Jason and Stephanie share one of their worst experi...
Awkward...Defining Your Swinging Style
16 Apr 2024
Contributed by Lukas
In this conversation, Jason and Stephanie Class discuss their swinging style and the importance of defining and communicating boundaries in the lifest...
Awkward... Exploring Your Kinks (with Babz_onthe_Rox)
12 Apr 2024
Contributed by Lukas
Summary In this conversation, Jason , Stephanie, and Babz discuss various kinks and fetishes they have encountered in the swinging lifestyle and thro...
Awkward…You got catfished!
12 Apr 2024
Contributed by Lukas
Takeaways Communication is key when introducing new sexual experiences into a relationship. Being patient and understanding with your partner's b...
Awkward…You want to go to a Swingers Resort
11 Apr 2024
Contributed by Lukas
Stephanie and Jason discuss the thought process leading up to their first trip to Hedonism in Jamaica, and what to expect if you might be an awkward f...
Awkward...You're still a Virgin
08 Apr 2024
Contributed by Lukas
Summary The Awkward Pillow Talk podcast discusses their unique approach to helping virgins lose their virginity. They share their experiences with re...
Awkward…you let your anxiety define your sexuality!
05 Apr 2024
Contributed by Lukas
We discuss Stephanie’s journey! Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
Awkward…Talking to your partner about trying something new
03 Apr 2024
Contributed by Lukas
Summary In this conversation, Jason and Stephanie discuss their experiences and challenges in exploring new sexual experiences as a couple. They shar...
Awkward…Embracing Your Sexuality While Everyone Is Watching!
02 Apr 2024
Contributed by Lukas
Summary In this episode of the Awkward Pillow Talk podcast, hosts Jason and Stephanie Klass introduce themselves and discuss the challenges of connec...
Awkward Pillow Talk (Trailer)
01 Apr 2024
Contributed by Lukas
A new episodeSupport this podcast at — https://redcircle.com/awkward-pillow-talk/donations