The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging

Kiley ‘Sexyswingerchic’
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  • SEXUALITY
  • UPDATED WEEKLY

The Pineapple Express  Once a swinger podcast… now a real-time journey through modern love. Hosted by Kiley — queer, non-monogamous, neurodivergent, ex-sex worker turned sex and relationship coach — The Pineapple Express explores the messy, magical, ever-evolving world of love, sex, intimacy, and emotional growth. This podcast is for anyone navigating: Non-monogamy, polyamory, or swingingMonogamy after openness (or vice versa)Relationship transitions, breakups, and rediscovering self-worthADHD, neurodivergence, and nervous system repair in loveSexual empowerment and authentic connection Each episode blends real-time storytelling, expert interviews, and unfiltered reflections on: Ethical non-monogamy, polyamory, and swingingEmotional intelligence and intimacy and of course SEX Boundaries, communication, and healing attachment woundsQueerness, identity exploration, and sex-positivityNeurodivergent love, pleasure, and partnershipYou’ll laugh, cry, and maybe even journal after. Kiley’s here to stir the cauldron — and remind you that pleasure, connection, and love are allowed to evolve. This isn’t your average relationship podcast. It’s personal. It’s sacred. It’s a little unhinged. And it’s exactly what you’ve been craving. Why Listen? Because you're not looking for perfect love — you’re looking for real love. Because you’re healing, growing, and rewriting the rules — and want company along the way. Subscribe now and ride The Pineapple Express, where we talk about sex, love, and everything in between — with zero judgment, just curiosity, courage, and connection.

  1. OCT 9

    114: From ER Nurse to Hotwife with Adult Content Creator Serenity Cox

    Send us a text In this episode of The Pineapple Express, I sit down with Serenity Cox — former ER nurse turned erotic content creator and hotwife lifestyle influencer — to explore her dramatic transformation, boundary-pushing relationship models, and how she’s rewriting the rules of desire and consent. We discuss: Her journey: from nursing in emergency care to filming and sharing intimate moments with her partner and the worldThe hotwife lifestyle: what it really means, negotiation, consent, and dismantling stigmaHow she handles judgment, shame, and the emotional terrain of non-monogamyThe crossover between erotic content, empowerment, and relational authenticityWhat sustaining desire looks like long-term, and how she envisions what’s next for her workIf you’ve been curious about ethical non-monogamy, erotic publication, or how to align your interior desires with your relational life — this one’s for you. Featured Guest Serenity Cox (Canada) — a content creator known for her evolution from ER nurse to high-profile erotic performer. She entered the adult content world through her “hotwifing” experiences and now works with major studios (such as Vixen Media Group) under exclusive contracts. She’s emerged as a bold voice in conversations about consent, relational transparency, and redefining erotic agency. Wikipedia+2 Amazon Music+2 You can find her website here: serenitycox.ca Wikipedia She’s active on Instagram, OnlyFans, and through her content platforms. worldwidecelebpodcast.com+2 Amazon Music+2 Episode in Grade A Nation where she shares her journey: “From Catholic School to Pornhub Award Winner — Serenity Now” Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 8m

  2. AUG 29

    113: How Parts Work Transforms Polyamory: Transforming Jealousy, Fear, and Attachment Wounds

    Send us a text In this episode, Kiley explores how Parts Work, most commonly associated with Dr. Richard C. Schwartz’s Internal Family Systems (IFS) model, can transform your experience of polyamory and consensual non-monogamy. You’ll learn how to identify your inner Managers, Firefighters, and Exiles, and how to lead from your calm, compassionate Self — even in the middle of jealousy, fear of abandonment, or metamour conflict. We’ll also connect these tools to Jessica Fern’s Polysecure, showing how parts work can help you earn secure attachment both within yourself and with your partners. Plus, Kiley shares her own journey of meeting protective and wounded parts with curiosity and compassion instead of reactivity. Referenced Resources & Books: No Bad Parts — Richard C. SchwartzInternal Family Systems Therapy, Second Edition — Richard C. Schwartz & Martha SweezyPolysecure — Jessica FernSelf-Therapy — Jay EarleyFree IFS meditations — IFS-Institute.comJay Earley’s Parts Work Exercises — SelfTherapy.orgWhether you’re new to parts work or deep into your own IFS journey, this episode offers practical tools for emotional regulation, self-compassion, and building security in the beautiful complexity of polyamory. Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    43 min

  3. AUG 22

    112: Anxious + Avoidant: Can This Relationship Ever Work? — with Jack from Polarity Unscripted

    Send us a text In this episode, Kiley sits down with Jack Bohannan from Polarity Unscripted to explore one of the most talked-about — and often misunderstood — relationship dynamics: the anxious–avoidant attachment pairing. Drawing from her own past relationship (where the answer to “can it work?” felt like a definite no), Kiley brings a candid, real-world perspective to the conversation, while Jack offers his deep expertise on polarity, emotional intimacy, and secure relating. Together, we break down: Why anxious and avoidant partners are so often drawn to each otherThe core fears each style brings into the relationshipWhat it actually takes to make this pairing work (and when to walk away)How to shift from triggering each other to co-regulating each otherPractical tools for healing your attachment style — whether you’re dating, nesting, or exploring non-monogamyThis episode blends attachment theory, , and Jack’s signature polarity framework to give you actionable steps you can use in your own relationships — no matter your style. 📌 Find Jack Online: Website: https://jackbohannan.comInstagram: https://instagram.com/polarityunscriptedYouTube: https://www.youtube.com/@PolarityUnscriptedIf you’ve ever wondered whether anxious and avoidant partners can build something lasting — or if you’ve lived the highs and lows of this dance yourself — this is the episode you don’t want to miss. Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off  https://www.thenonmonogamycardgame.com/products/the-game Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 8m

  4. AUG 15

    111:The Damage Of Decolonizing Love & The Polyamory Community,Race, and the Swinger's Lifestyle— with Tiffany @RealPolyLife

    Send us a text The Damage of Decolonizing Love & Black Polyamory: Tiffany @RealPolyLife on Race, Community & Swinging  Join us for a powerful conversation with Tiffany (@RealPolyLife) https://www.instagram.com/realpolylife?igsh=MTRhYWg4Yngwd3h5Zg== a Black polyamorous educator and influencer, as she unpacks the complex intersections of  race, and intimate relationship structures within the polyamory and swinger communities. We dive into how the not so well-meaning efforts of 'decolonizing love' can inadvertently cause harm, especially for Black women navigating ethical non-monogamy. In this episode, you'll hear about: The tensions between polyamory, race dynamics, and swinger culture in communities of color.Stories and insights from Black women in poly to broaden understanding and visibility.Tiffany’s work in centering Black voices in polyamorous narratives via her platform RealPolyLife.Resources such as:Black & Poly, a culturally rich poly blog/community designed to foster connection and honest discussion in Black-centered polyamorous spaces YouTube Therapy for Black Girls Session 182, featuring Ruby B. Johnson—a polyamorous Black queer therapist—who addresses stigma, communication, and tools for ethical non-monogamy Therapy for Black Girls. Psychology of Black Womanhood entry “Black Women & Polyamory”, spotlighting Dr. Jenn M. Jackson’s research on the experiences and challenges of Black women in poly relationships Psych of Black Woman Online communities like Black & Poly™ and BlackSupport the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 17m

  5. JUL 11

    110: 'Tolyamory' and The Dangers Of Practicing Non Monogamy To Keep Your Partner

    Send us a text Let’s talk about the thing no one wants to admit: sometimes we say yes to non-monogamy not because we want to—but because we’re afraid to lose someone we love. In this episode, we dive deep into the term “tolyamory” (coined by Dan Savage), the danger of choosing open relationships out of fear instead of desire, and how to tell if you’re actually aligned with non-monogamy… or just tolerating it. We’ll unpack: The red flags of “tolyamory”Why consent isn’t just a checkbox—it’s a felt senseHow to check in with your nervous system before saying yesWhat to do if your partner wants non-monogamy and you don’tHow to reclaim your voice, your boundaries, and your truth—even when it’s hardWhether you’re the one asking or being asked to open up, this episode is for you. Let’s stop calling it love when it’s really fear. 💔➡️💖 DAY OF VISIBILITY EVENTS  https://www.eventbrite.com/e/3rd-annual-day-of-visibility-for-non-monogamy-picnic-in-the-park-tickets-1398059807519 https://www.weekofvisibility.com/ Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    50 min

  6. JUL 4

    109: Hard Truths: Women’s Pleasure, Shame, and the Silent Impact of ED With Dr. Elliot Justin

    Send us a text In this powerful episode of The Pineapple Express, sex and relationship coach Kiley George sits down with Dr. Elliot Justin, founder of FirmTech and a leading voice in sexual wellness innovation, to explore the often-overlooked emotional and physical impacts of erectile dysfunction (ED) on women. We talk about how ED affects women's sexual confidence, why so many partners feel shame, guilt, or self-blame, and how sex tech tools like FirmTech’s Ring are helping couples reconnect with pleasure, intimacy, and honest communication. This episode blends scientific insights, real talk about libido, and relationship tips for navigating intimacy when things aren’t going “as planned.” If you’ve ever wondered how to support a partner with ED—or how to reclaim your own arousal in the process—this one’s for you. Why ED isn’t just “a man’s issue”How shame and silence affect female arousalWomen’s hidden grief around unspoken rejectionReframing ED with science, compassion, and toolsHow to have the conversation with your partnerThe role of FirmTech's Ring in enhancing erection strength and pleasure for both partnersAvailable on Apple Podcasts, Spotify, and everywhere you stream your favorite shows. Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 5m

  7. JUN 27

    108: How to Throw a Kick-Ass Play Party (and Be a Kick-Ass Guest) with Ally Isman

    Send us a text Ever wondered what makes a play party unforgettable (for all the right reasons)?  In this sizzling episode of The Pineapple Express, I’m joined by Ally Isman, founder of Passport2Pleasure and mastermind behind the KAVANOS: Lisbon Wedding Night experience—an invite-only, immersive destination play party held in a historic Portuguese palace. Together, we break down everything you need to know to host or attend a play party like a pro, from curating energy and consent culture to creating sacred sensual spaces that feel both sexy and safe. If you're curious about throwing your own event, leveling up your guest etiquette, or just want a peek behind the velvet curtain of elite erotic events—this episode is your golden ticket. 🔍 Keywords: how to host a play party, KAVANOS Lisbon, sex-positive events, Ally Isman, Passport2Pleasure, consent at play parties, how to attend a sex party, non-monogamy events, luxury swinger events, erotic event planning ✨ We talk about: What makes a play party actually workCommon mistakes and how to avoid awkward energyHow to design an intentional, inclusive guest listErotic aesthetics, rituals, and ambianceConsent communication and comfort cultureWhy KAVANOS is one of the most exclusive sensual events in the world—and how to apply before it disappears forever Apply now for KAVANOS: Lisbon Wedding Night (August 2) via Passport2Pleasure.com and use “PINEAPPLE” for expedited review.This is not your average play party. This is art, eros, and elevation. Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 11m

  8. JUN 22

    107: Building Real Connection In Swinging and Polyamory with The Non-Monogamy Card Game

    Send us a text Want to deepen your relationships without another awkward check-in? In this episode of The Pineapple Express, we explore how The Non-Monogamy Card Game is changing the way we connect—with ourselves, our partners, and our playmates. Whether you're polyamorous, exploring ethical non-monogamy, or just want better conversations in your situationships, this tool is pure gold. Join me and Ayala & Kristen the creators of The Non Monogamy Card Game as we share how connection, vulnerability, and communication games can ignite intimacy and help non-monogamous folks cut through small talk and get to the juicy stuff.  We talk about:  – How to use the card game on dates or at play parties  – Why asking better questions leads to better connections   – Connection rituals for polycules and swingers  – How to avoid surface-level relating in non-monogamy Grab your cards, press play, and let’s get real. Use my exclusive code PINEAPPLE10 for 10% off when you purchase The Non Monogamy Card Game  https://www.thenonmonogamycardgame.com/products/the-game Support the show 🎙️ The Pineapple Express Podcast Subscribe to my Substack for exclusive content: The Pineapple Express Substack. 💡 Events & Coaching Coaching sessions: Book time with me. 💜 Advocacy & Community Action Support equity and sexual freedom with the National Coalition for Sexual Freedom. OPEN's Free Peer Support Group 🛍️ Exclusive Deals Just for You Get The Non Monogamy Card Game and use my exclusive code PINEAPPLE10 for 10% Off https://www.thenonmonogamycardgame.com/products/the-game FirmTech Wearable Tech | Male Enhancement Rings | Shop now and get 15% off with code sexyswingerchick. SENSE Shop | Condoms & Lube | Explore the collection and save 15% with code sexyswingerchic. Sultry Vixen Dancewear | Exotic Outfits | Shop here and enjoy 15% off with code sexyswingerchic. 💬 Let’s keep the conversation going! Follow me for up...

    1h 19m
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Ratings & Reviews

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out of 5
2 Ratings

About

The Pineapple Express  Once a swinger podcast… now a real-time journey through modern love. Hosted by Kiley — queer, non-monogamous, neurodivergent, ex-sex worker turned sex and relationship coach — The Pineapple Express explores the messy, magical, ever-evolving world of love, sex, intimacy, and emotional growth. This podcast is for anyone navigating: Non-monogamy, polyamory, or swingingMonogamy after openness (or vice versa)Relationship transitions, breakups, and rediscovering self-worthADHD, neurodivergence, and nervous system repair in loveSexual empowerment and authentic connection Each episode blends real-time storytelling, expert interviews, and unfiltered reflections on: Ethical non-monogamy, polyamory, and swingingEmotional intelligence and intimacy and of course SEX Boundaries, communication, and healing attachment woundsQueerness, identity exploration, and sex-positivityNeurodivergent love, pleasure, and partnershipYou’ll laugh, cry, and maybe even journal after. Kiley’s here to stir the cauldron — and remind you that pleasure, connection, and love are allowed to evolve. This isn’t your average relationship podcast. It’s personal. It’s sacred. It’s a little unhinged. And it’s exactly what you’ve been craving. Why Listen? Because you're not looking for perfect love — you’re looking for real love. Because you’re healing, growing, and rewriting the rules — and want company along the way. Subscribe now and ride The Pineapple Express, where we talk about sex, love, and everything in between — with zero judgment, just curiosity, courage, and connection.

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