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

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

🎙️ 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

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

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Get Tested!

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

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

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

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)

🔹 @missbehavinxo (No XXX content unless blurred!)

Instagram

🔹 @missbehavinxoxo

🔹 @missbehavinxoxo1

🔹 @missbehavinxoxo5

Fansly

🔹 @peachesnbourbon

🔹 @jeeves458

ManyVids

🔹 @missbehavinxoxo

🔹 @jeeves458

Loyal Fans

🔹 @missbehavinxoxo

SextPanther

🔹 MissBehavinxoxo

👉 Subscribe, like, and turn on notifications so you don’t miss it! 🎙️

#Podcast #AwkwardPillowTalk #MissBehavin #SexPositive #AdultIndustry #Interview

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

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 This Episode:

✅ A couple’s journey from curiosity to taking the plunge

✅ How we vet people and avoid the weirdos (yes, we have stories)

✅ The nerves, the anticipation, and the “OMG, we’re actually doing this” moment

✅ A behind-the-scenes look at how we make these experiences fun, natural, and hot

🎥 Want to SEE what happened?

We filmed it all with five cameras, close-ups, and full action. This is one of the hottest and most real videos we’ve ever made. You can find it on:

🔹 Fansly: The full uncensored experience on our Virgin Connoisseur Tier

🔹 OnlyFans: OnlyFans.com/StephanieClass

🔹 PPV Release: Dropping this week for $20

💬 What was it really like?

This couple was awkward, excited, and totally down for the experience. We talk about boundaries, nerves, and how they felt before, during, and after. Plus, we keep it real and fun, because swinging isn’t just about sex—it’s about enjoying the moment without pressure.

🔥 Join the Awkward Sex-Lovers Community

We’re building a judgment-free, fun, and kinky space where people can explore and learn. If you’ve ever been curious, this is your invitation!

👉 Subscribe, Watch, and Join Us at VirginitySnatchers.com

#Swinging #FirstTimeSwingers #Podcast #AwkwardPillowTalk #Lifestyle #Couples #OnlyFans #Fansly

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

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 vibrator” to “Hand me that strap-on.”

You’ll also hear about our ever-growing community of open-minded (and sometimes hilariously awkward) individuals who finally found their people. Join us in building an unapologetically sex-positive, judgment-free zone—you’ll be glad you did. And if you’re into spicing things up, catch our tips on meeting new play partners on SDC (it’s where we’re filtering all our future, uh, “adventures”).

Plus, we’re spilling on our new favorite must-haves from Common Confidential. They sent over a blanket, “love rags,” and massage butter that doubles as lube—yes, it’s as mind-blowing as it sounds. Stick around for an honest, hilarious, and (occasionally) TMI discussion about embracing the awkward side of sex, relationships, and everything in between. Because weird is wonderful—and we’re here for it!

Tune in to hear:

• Steph’s journey from zero orgasms to all the orgasms

• The power of open communication in (really) spicing up your relationship

• Partnering with SDC and building a no-judgment community

• A behind-the-scenes look at our new favorite bedroom products

• Why awkward can actually be the hottest way to live!

Don’t forget: Mark your calendars for our free SDC livestream on January 29, 2025 at 12pm EST—we’ll be sharing more tales of awkwardness, tips on living authentically, and maybe a brand-new move or two.

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

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 separate work from family life 💼➡️👨‍👩‍👧‍👦

• The challenges and rewards of being adult creators

• Exciting new filming ideas for 2025 (think hot wives, secret spouses, and erotic photo shoots 📸🔥)

• Why judgment from others won’t stop us from living our truth 💪

Plus, we share updates on our favorite products (looking at you, Kums Chocolate 🍫), new advertiser opportunities, and our plans to offer free relationship coaching sessions for a few lucky couples.

As always, we keep it real, raw, and awkwardly fun. Don’t miss it!

👉 Check out the TikTok Shop: Awkward Pillow Talk

👉 Visit our site: VirginitySnatchers.com

👉 Email us for coaching inquiries or partnerships: [email protected]

#AwkwardPillowTalk #YearOfTheHo #LifestylePodcast #AdultContentCreators #RelationshipGoals #FamilyFirst #TikTokShop #SexPositive #CouplesCoaching #VirginitySnatchers #PodcastLife #FloridaLife #NoJudgmentZone

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

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.

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