Awkward Pillow Talk

Awkward Pillow Talk

Download on the App Store

Awkward Pillow Talk episodes

  • The Vibrator Was Normal - Then America Made It Obscene

    The Filthy History of Being Normal follows the paper trail behind the things society taught us to feel weird about.

    Sex. Relationships. Bodies. Pleasure. The products we use, the laws written around them, and the people who decided what was—or wasn’t—acceptable.

    This isn’t a show built around hot takes. We dig into court cases, patents, newspaper archives, advertising, legislation and the real people behind the history to understand how yesterday’s moral panic became today’s idea of “normal.”

    Episode 2: The Vibrator

    Vibrators were openly advertised to American consumers more than a century ago. So how did they become something that had to be hidden, disguised and sometimes even outlawed?

    We follow the story from the rise of Anthony Comstock and federal obscenity enforcement through the changing vibrator industry, a 2003 Texas arrest involving the sale of a vibrator, Dame Products’ 2019 fight with New York’s MTA over advertising, and the strange legacy behind phrases like “novelty item” that still appear on packaging today.

    It’s the history of a sex toy—but it’s also a story about commerce, censorship, shame and who gets the power to define normal.

    Hosted by Jason Class.

    New episodes weekly.

    See the video version on Youtube.

    Sponsorship inquiries: [email protected]

    14 min
  • The History of the O: 4,000 Years of Getting It Wrong

    Two people had sex in an MRI machine in 1999. The paper became one of the most-viewed articles the British Medical Journal has ever published, out of everything, in a journal that goes back to 1840.


    That's where this starts. It goes back 4,000 years from there.


    Egyptian creation myths. A 2,300-year-old comedy sketch about where to buy a good sex toy. Two Renaissance anatomists in a screaming match over who "discovered" something women had known about the whole time. The most famous fun fact in this entire field, which turns out to be completely fabricated and fooled academia for nineteen years.


    And the number at the end that explains why the orgasm gap exists, and why it isn't what you think.


    Every claim in this episode was fact-checked, and the ones that didn't survive checking are named as such. Especially the fun ones.


    Episode one of A Filthy History of Being Normal.


    SOURCES

    Lieberman & Schatzberg, "A Failure of Academic Quality Control" (2018)

    Frederick et al., Archives of Sexual Behavior (2018), n=52,588

    Komisaruk et al., Brain Research (2004)

    Herbenick & Fortenberry, Sexual and Relationship Therapy (2012)

    O'Connell et al. (1998, 2005)


    The book is The Awkward Couple's Guide to Getting Weird. Same idea pointed at your actual relationship instead of at history. awkwardxxx.com


    Next episode: virginity. There is no test, there has never been a test, and the thing everyone pictures is a rare birth defect.

    16 min
  • This Show Is a Love Letter to My Wife | A Filthy History of Being Normal

    My wife spent years quietly assuming she was the weird one. So I spent time looking for proof that she wasn't.


    What I found instead was that most of the famous facts are made up.


    The average measurement everybody quotes came from men measuring themselves at home and mailing the card back. Doctors spent sixty years hunting for a poison in menstrual blood that was never there. The most repeated fact about the vibrator fooled academia for nineteen years before anyone checked the footnotes.


    This is Awkward Pillow Talk, and it's a different show than it was. Same subject, completely different approach. Every claim gets fact-checked, and the ones that don't survive get named out loud. Especially the fun ones.


    Season one is A Filthy History of Being Normal: orgasms, virginity, sex toys, squirting, swallowing, sapphic attraction, anal, throuples, swinging, sex vacations, and whatever turns out to be next.


    For anyone who needs to know why before they can relax.


    First episode is the history of the orgasm. New episodes weekly.


    The book is The Awkward Couple's Guide to Getting Weird. Same idea pointed at your actual relationship instead of at history. awkwardxxx.com


    KindaIntoThat.com is a quiz that tells you what you're actually into and gives you an anonymous code to compare with somebody else. Nobody has to say anything out loud first.


    Earlier episodes of this feed featured Jason and Stephanie Class in conversation and will be made available again at a future date.

    3 min
  • Awkward...First Time Jitters

    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 bus ride.” Along the way, Jason and Steph break down what worked, what didn’t, and why communication and boundaries are the only way to make new experiences work without blowing up your relationship.


    You’ll also hear their practical tips—like why eating cheese fries before a playdate is a terrible idea, how alcohol really affects nerves (and erections), and why setting the right rules and expectations will save you from disaster.


    If you’ve ever felt the weight of nerves before trying something new with your partner, this episode proves you’re not alone. Awkward jitters are normal, but with the right mindset, they can actually bring you closer together.


    👉 Join the conversation in their Skool communities:


    • Awkward Couples (free group for couples wanting better communication & intimacy)
    • Virgin to Victory (paid group for single guys who need honest, no-BS advice)


    📚 Grab their book: The Awkward Couple’s Guide to Getting Weird for more real-life stories and practical tools.

    🎙️ And don’t miss their free live webinar on First Time Jitters happening September 17th at 9 PM EST on SDC (sign up at awkwardxxx.com).



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    25 min
  • Awkward…Data-Driven Boners (featuring FirmTech CEO Dr. Elliot Justin) + Virgins 22 & 23

    Awkward…Data-Driven Boners (featuring FirmTech CEO Dr. Elliot Justin) + Virgins 22 & 23


    In 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 Virgin #23—two awkward first-time experiences that remind us why this project exists in the first place. Plus, big news: our SKOOL communities are live!


    • The Awkward Couples Group (free) – a safe space for couples to connect, laugh, and explore.
    • From Virgin to Victory (paid) – coaching, dating help, and confidence-building for men ready to take the leap.


    Check out FirmTech at FirmTech.com

    Join our communities at VirginitySnatchers.com


    Follow us on TikTok: AwkwardPillowTalk, AwkwardReviews, and StephanieClassX



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    52 min
  • Awkward...Nude Beach Review

    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, sunscreen, and unsolicited staring).


    Plus, we share two very different playdate stories: one with a pool guy who came ready to perform (literally), and another that proves whiskey and confidence don’t always mix. Whether you’re beach-curious or just here for the chaos, this episode is everything Awkward Pillow Talk promises — funny, honest, sexy, and unapologetically real.


    🔗 Get the book:VirginitySnatchers.com or Look for it on Amazon!

    📸 Fansly: All videos unlocked for $100

    TheJasonClass.com



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    33 min
  • Awkward...Update 05/13/25

    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-pillow-talk/donations
    1 min
  • Awkward...Stories about Hedo with Chris Santilli

    🎙️ 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 hilarious, honest, and jaw-dropping stories from the world’s most notorious clothing-optional resort. We talk about what to expect at Hedo, why it’s so empowering (especially for women), and how it helps couples break through anxiety, judgment, and sexual shame.


    Chris also shares exclusive details about her upcoming book:

    📘 Before Harry Met Hedo – the unauthorized origin story of Hedonism II (1976–2012), packed with behind-the-scenes info and unforgettable guests.


    🧳 What We Talk About in This Episode:

    • What is Hedonism II really like?

    • How to prepare for a clothing-optional resort

    • The truth about swinger travel & adult-only vacations

    • Body image, confidence, and letting go of shame

    • Funny, awkward, and sexy stories from real Hedo trips

    • Chris Santilli’s books: The Naked Truth About Hedonism II & Before Harry Met Hedo


    🔥 Special Offer for Stephanie Class Fans!

    👉 Go to https://VirginitySnatchers.com for 60% OFF — just for being a fan of Stephanie!


    📬 Sign Up for Chris Santilli’s Free Weekly Newsletter:

    ➡️ https://chrissantilli.com

    📘 Book info + author updates

    🚫 No spam. Ever.

    📲 Facebook: https://www.facebook.com/chris.santilli.902/


    👄 Awkward Pillow Talk is your new favorite podcast about:

    • Real relationships

    • Swinger lifestyle stories

    • Adult travel tips

    • Sex positivity

    • Marriage, anxiety, and finding freedom in unexpected places


    💬 New episodes drop weekly. Don’t forget to like, comment, subscribe, and share if you love honest, hilarious, and no-holds-barred conversations.


    #hedonismII #lifestyleresort #swingerspodcast #adulttravel #nuderesort #chrisSantilli #BeforeHarryMetHedo #StephanieClass #awkwardpillowtalk #hedotravel #hedonismstories #sexpositivity #clothingoptional #swingervacation



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    46 min
  • Awkward… A March Festivus (The Airing of Grievances)

    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 product

    🔥 A game-changing health discovery (STD testing, allergies, and more!)

    🔥 The struggle to find authentic friendships in the lifestyle

    🔥 Why losing a friendship can hurt just as much as a breakup

    🔥 The challenges of being content creators, swingers, and parents


    Plus, we’ve got some wild stories, a little oversharing (as always), and an exclusive look at a product that might just change your sex life.


    Catch the full, unfiltered convo on YouTube and RedCircle! Don’t forget to like, subscribe, and join us on this crazy ride.


    See More - AwkwardPillowTalk.com

    💬 Join the Awkwardly Sexy Society: AwkwardXXX.com


    Get some Honey - Vitoo.com/StephanieClassX


    Get Tested!


    MyBLSLabs.com/AwkwardTalk10


    #AwkwardPillowTalk #Podcast #Swingers #Lifestyle #Relationships #Unfiltered #FriendshipDrama #MentalHealth #HonestTalk



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    45 min
  • Awkward...Penguins and Pocket Pussies

    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, and our ongoing battle with nosy neighbors who just love spreading gossip. Plus, we break down the bizarre realities of selling sex toys modeled after our own bodies (spoiler: Jason wants an Excalibur display set), and how Ashley handles the never-ending “Do you do meetups?” questions.


    Oh, and we test out Twinkle Tongue, a product that may or may not leave Stephanie drooling mid-interview.


    🔹 Follow AskAshley479:

    TikTok: @AskAshley479

    Instagram: @AskAshley479


    🎙️ Listen to Awkward Pillow Talk on all major podcast platforms!



    🔥 Want more exclusive content?

    👀 Check out VirginitySnatchers.com


    Trying to connect with real swingers? Try AwkwardXXX.com


    #AwkwardPillowTalk #AskAshley479 #Swinging #SocialMediaBans #PenguinsBite #AdultContentCreator #TwinkleTongue #OnlyFans #Podcast



    Support this podcast at — https://redcircle.com/awkward-pillow-talk/donations
    49 min

About Awkward Pillow Talk

From the publisher's feed

The history of sex, checked against actual sources, told by a guy in a bathrobe who read too much.


I made this for my wife. She spent years quietly assuming she was the weird one,…

More shows like Awkward Pillow Talk

Strictly Anonymous Confessions by Kathy Kay

Strictly Anonymous Confessions

1,604 Listeners

Front Porch Swingers by Brenna and Brian

Front Porch Swingers

518 Listeners

The Venus Cuckoldress Podcast by Venus

The Venus Cuckoldress Podcast

465 Listeners

4OURPLAY - A Swinger Podcast by Bella & Jase - Millennial Swingers

4OURPLAY - A Swinger Podcast

330 Listeners

Friends With A Twist: A Swinger Podcast by Friends With A Twist: A Swinger Podcast

Friends With A Twist: A Swinger Podcast

279 Listeners

Hump Day Quickies : Swinger Confessions by Greg & Nessa Quickies

Hump Day Quickies : Swinger Confessions

327 Listeners

Hotwife Diaries Podcast by AussieCate and Mrs Milford

Hotwife Diaries Podcast

140 Listeners

Diary of a Swinging Couple by Diary of a Swinging Couple

Diary of a Swinging Couple

135 Listeners

THE MONOGAMISH MARRIAGE by Kate & Liam

THE MONOGAMISH MARRIAGE

181 Listeners

Vanilla Swingers: Swinger Podcast, Unfiltered AF by Kat & Leo

Vanilla Swingers: Swinger Podcast, Unfiltered AF

369 Listeners

Pineapple Pinup: Hotwife Swingers Life by Tasty Tress

Pineapple Pinup: Hotwife Swingers Life

144 Listeners

Bulls & Queens | Swinger Podcast for Cuckolds Hotwives & Bulls by Doc Chocolate - Sex Coach for Cucks & Hotwives

Bulls & Queens | Swinger Podcast for Cuckolds Hotwives & Bulls

121 Listeners

Cuck My Life Podcast by Cuck My Life Podcast

Cuck My Life Podcast

56 Listeners

Hotwife Haven by Hotwife Ember Rae

Hotwife Haven

101 Listeners

Two Plus Two: The Swinger Podcast for Couples by Zack and Josie

Two Plus Two: The Swinger Podcast for Couples

112 Listeners