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

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

Kiley ‘Sexyswingerchic’ thepineappleexpresspodcast.buzzsprout.com

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 swinging
  • Monogamy after openness (or vice versa)
  • Relationship transitions, breakups, and rediscovering self-worth
  • ADHD, neurodivergence, and nervous system repair in love
  • Sexual empowerment and authentic connection


Each episode blends real-time storytelling, expert interviews, and unfiltered reflections on:

  • Ethical non-monogamy, polyamory, and swinging
  • Emotional intelligence and intimacy and of course SEX 
  • Boundaries, communication, and healing attachment wounds
  • Queerness, identity exploration, and sex-positivity
  • Neurodivergent love, pleasure, and partnership

You’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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Episodes

54:Stigma and Non Monogamy with Ro Moed 'Unapolygetically'

Send us a text On this episode of the Pineapple Express podcast Kiley sits down with Ro Moëd, a relationship coach in non monogamous spaces, a writer and content creator. Kiley and Ro dive into the controversial topic of toxic monogamy and stigma associated with non monogamy. To learn more about Unapolygetically and find out more about them visit their website https://campsite.bio/unapolygetically?fbclid=PAAabLvfbbU6uvBm9jZcq3fmHHkFe1zoKrflH_1z35jwJqCti8ZqA6wFup4oE_aem_ATlNaBQqiq9bMBgn0LegAkPXFh...

Feb 23, 20241 hr 22 minSeason 2Ep. 3

53: Sexual Diversity and Neurodivergency with Tanja Diamond

Send us a text Tanja Diamond is a polymath, Tantra Lineage Holder, Business and Life Strategist. Her 45 years of unique worldwide education, extensive knowledge in thousands of subjects, and certifications in hundreds of modalities, make her the go-to for everyone who needs solutions and results quickly. Tanja is a five-time #1 International best-selling author, 2x International TEDx speaker and the creator of Modern Tantra – The Seven Tantras of Integrated Intelligence. Her coach certification ...

Feb 16, 202448 minSeason 2Ep. 1

52: Sex Work and Stripper Appropriation With Poler.Rosie

Send us a text Follow poler Rosie on social media https://www.instagram.com/poler.rosie?igsh=dmU0cjJzMzE1Nzk5 All My Links To Learn More About Me https://sexyswingerchic.net/ Onlyfans https://onlyfans.com/sexyswingerchic Find me on social media IG https://www.instagram.com/thepineappleexpresspodcast?igsh=MWdhZ2owY3d0dDhlNQ%3D%3D&utm_source=qr TikTok https://www.tiktok.com/@sexyswingerchic91?_t=8k7KsW0pvQI&_r=1 Cleveland area Non Monogamous humans join our Facebook group https://www.faceb...

Feb 09, 20241 hr 25 minSeason 2Ep. 1

51: DEI in Swinger Spaces with Professor.Playtime

Send us a text In this compelling episode of the Pineapple Express podcast we explore the complexities of non-monogamous relationships through the lens of diversity, equitability, and inclusion. From illuminating personal stories to thought-provoking discussions, we delve into the multifaceted ways in which non-monogamous communities navigate equality, representation, and belonging. Join us as we uncover the challenges, triumphs, and ongoing journeys toward fostering a more inclusive and equitab...

Feb 02, 20241 hr 40 minSeason 2Ep. 2

50: How To Join The Swingers Lifestyle with Kiley

Send us a text 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.thenonmonogamycar...

Jan 19, 202435 minSeason 1Ep. 50

49: Safety Tips For The Swingers Lifestyle with Kiley

Send us a text 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.thenonmonogamycar...

Jan 12, 202458 min

48:The Parallels Between Swinging And Sex Work With Kiley

Send us a text On this episode of the Pineapple Express Podcast Kiley talks about her experience as a sex worker and the parallels it has to her swinging lifestyle. She talks about elements of consent, negotiation, boundaries, communication, and the exploration of sexual desires. She gives stories and opinions that some may not like hearing, but these are perspectives coming from someone in the sex work industry. To support sex workers please consider donating to The Woodhull Freedom Foundation ...

Jan 05, 202452 minSeason 1Ep. 48

47: Event Hosting and Swinger Influencer Power Dynamics with Mizzy Bender

Send us a text Today on… The Pineapple Express Podcast we are talking about event hosting and power dynamics in the swinger lifestyle. Join host Kiley and her guest Mizzy Bender, seasoned content creators, as they dive into the world of event coordination, explore the intricacies of power dynamics, and share insightful tips for thriving in the swinger lifestyle. Get ready for candid conversations, insights, and practical advice that will elevate your understanding of the swinger lifestyle. Find ...

Dec 29, 20231 hr 15 minSeason 1Ep. 47

46: The Nuances Of being a Cuckquean with Kink and Intimacy Coach Julieta

Send us a text The term "CuckQuean" refers to a woman who experiences sexual arousal from watching her partner engage in sexual activity with someone else. The term is typically used within the context of consensual non-monogamous relationships and is often associated with BDSM dynamics. Are you a CuckQuean or curious about cuckqueaning? This is the podcast for you. For more info on Julieta visit her website. https://stan.store/julietachiara?fbclid=PAAaYDAFDK1Tou7rXLBYWheYVdUZ2bbnuN6hCIbTDVpAVDR...

Dec 22, 20231 hr 1 minSeason 1Ep. 46

45: Relationship Anarchy with Annie Undone

Send us a text Meet Annie Undone a writer and relationship anarchist and they are deconstructing normatively in all relationship structures Follow them on IG https://instagram.com/annie_undone?igshid=OGQ5ZDc2ODk2ZA== Here are some resources from the podcast https://theanarchistlibrary.org/library/andie-nordgren-the-short-instructional-manifesto-for-relationship-anarchy To learn more about Annie Undone and all the amazing things they are doing in this world here is a link to their website https:/...

Dec 15, 202354 minSeason 1Ep. 45

44: Non Monogamy and Spirituality With Clara from Conscious Polyamory

Send us a text Meet Clara from Conscious Polyamory Resources Teachings on Love, by Thich Nhat Hanh https://amzn.to/40Xtyma When things fall apart, by Pema Chodron https://amzn.to/47tjhR4 Spiritual Polyamory https://amzn.to/3SWXNrb Conscious Polyamory Blog https://consciouspolyamory.org/ My coaching website is LIVE https://www.consciousloveconnectioncoach.com/ Swinger Websites : Find all the best Swinger Websites/apps on my website https://sexyswingerchic.net/ Club Eros CLEVELAND https://cluberos...

Nov 24, 202357 minSeason 1Ep. 44

43: Swinger Talk: Being Grateful for your partner and Non Monogamy and Swinging

Send us a text My coaching website is LIVE https://www.consciousloveconnectioncoach.com/ Swinger Websites : SDC Kasidie https://theswingnation.info/?fbclid=PAAaYO8_1ww28dTbwC3Er2SAU5vVTlx03z8GlHhRKMdIDrbdcfCgnNnYfqDRA_aem_AeXcQC8qqYgu9PP6dqg_ely-fVnpo9L6-uLCZw5t48pki8IFoQ35pgiER-SSaFvHnhY SLS https://www.swinglifestyle.com/ 3fun https://www.go3fun.co/ad/TK10098 Club Eros CLEVELAND https://cluberoscleveland.com Email us at: thepineappleexpresspodcast@gmail.com Onlyfans https://onlyfans.com/sexysw...

Nov 17, 202338 minSeason 1Ep. 42

42: Swinger Education: How to Join The Swinger Lifestyle And Find Success As A Single Male

Send us a text Swinger Websites : SDC Kasidie https://theswingnation.info/?fbclid=PAAaYO8_1ww28dTbwC3Er2SAU5vVTlx03z8GlHhRKMdIDrbdcfCgnNnYfqDRA_aem_AeXcQC8qqYgu9PP6dqg_ely-fVnpo9L6-uLCZw5t48pki8IFoQ35pgiER-SSaFvHnhY SLS https://www.swinglifestyle.com/ 3fun https://www.go3fun.co/ad/TK10098 Club Eros CLEVELAND https://cluberoscleveland.com Email us at: thepineappleexpresspodcast@gmail.com Onlyfans https://onlyfans.com/sexyswingerchic Discord: https://discord.gg/swingersociety If you like this podc...

Nov 10, 202344 minSeason 1Ep. 41

41: Let’s Talk About Swinging: How to approach your partner about joining the Swinger Lifestyle with Swinger Lifestyle Coach Lauren

Send us a text Welcome to another exciting episode of The Pineapple Express Podcast. . In today's episode we'll be discussing how to initiate a conversation with your partner about exploring non-monogamy in your relationship. So get ready to open up your minds and hearts as we embark on this exciting journey. Find out more about Lauren and what she offers here https://linktr.ee/swinginglifestylecoach?fbclid=PAAabBUwOyETQgi8YEOCVhfDbKDbQKKHrnZEaZHU0nEJBxvz0Kb3V8k6Qmfp8_aem_AZGI9D0hlozPwwp_6FTDmup...

Nov 03, 20231 hr 12 minSeason 1Ep. 40

40: Swinger Education 'Tips for dealing with jealousy and insecurity in Non Monogamy' with Professor Playtime

Send us a text On this episode of The Pineapple Express podcast Kiley talks with relationship and trauma informed intimacy coach Professor Playtime about jealousy and insecurity in non-monogamy .They provide valuable discussions and insights for individuals navigating open relationships and the swinging lifestyle. On this episode explore the complex emotions of jealousy and insecurity that can arise. The goal of this podcast is to empower individuals interested in or already practicing non-monog...

Oct 27, 202356 minSeason 1Ep. 40

39: Swinger Horror Stories With BostonSwingerKing

Send us a text Join us on The Pineapple Express Podcast as Kiley and Joe ‘Boston Swinger King’ talk about their hilarious and unfiltered Swinger horror stories just in time for Halloween. Find out more about Joe BostonSwingerKing https://linktr.ee/bostonswingerqueen Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs •Club Eros CLEVELAND https://cluberoscleveland.com Email us at: thepineappleexpresspodcast@gmail.com Onlyfans https://onlyfans.com/sexyswingerchic Discord: https://disc...

Oct 20, 202359 minSeason 1Ep. 38

38: Swinger Event Review: Secrets "A Weekend To Remember" With BostonSwingerKing

Send us a text Join us on the Pineapple Express as we dive into the captivating world of swinging and talk about our clothing optional wedding at Secrets Hideaway - where love, adventure, and exploration intertwine. Join Brad and Kiley and Kiley and Joe as we wrap up our amazing weekend. Find out more about Joe BostonSwingerKing https://linktr.ee/bostonswingerqueen Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs •Club Eros CLEVELAND https://cluberoscleveland.com Email us at: the...

Oct 13, 20231 hr 52 minSeason 1Ep. 36

37: Navigating Consent and Predatory Behavior in the Swinger Lifestyle With Susan and Tess from The National Coalition For Sexual Freedom

Send us a text Join host Kiley as she chats with Tess and Susan from NCSF (National Coalition for Sexual Freedom) in a thought-provoking episode of Pineapple Express podcast as they tackle the crucial topics of consent and predatory behavior within the swinger lifestyle. With their wealth of experience and expert insights, they guide us through the nuanced landscape of boundaries, highlighting the importance of open communication and respectful interactions. Get ready for an eye-opening conversa...

Sep 08, 20231 hr 39 minSeason 1Ep. 35

36: Navigating the journey of Polyamory with The Poly (Pod)cast

Send us a text Dive into the fascinating world of polyamory with Siobhan and Rich from The Poly (Pod)Cast as they explore the depths of love, connection, and open relationships on the Pineapple Express Podcast . Join us as we all share our personal journeys, insights, and advice on navigating the complexities of polyamory. From communication skills to breaking stigmas, let's unpack the beautiful tapestry of multiple loves. Tune in as we embrace the possibilities of love in all its forms. Find ou...

Sep 01, 20231 hr 12 minSeason 1Ep. 35

35:Swinger Sexual Wellness and Prioritizing Women's Pleasure with Sexpert and Intimacy Expert Susan Bratton

Send us a text On this episode of “The Pineapple Express Podcast” ride along with Kiley in a thought-provoking conversation with Susan Bratton, an esteemed intimacy expert devoted to revolutionizing the way society perceives and prioritizes women's pleasure and overall sexual wellness. In a world often dominated by male-centric narratives, Susan takes us on a journey to unravel and challenge societal norms surrounding female sexuality. Brace yourself for a candid discussion that defies taboos an...

Aug 25, 20231 hr 18 minSeason 1Ep. 34

34: Swinger Stories 'The Ethics Of Unicorn Hunting and OPP in the Swinger Lifestyle' with SwingerED

Send us a text On this episode of The Pineapple Express Podcast enter the enchanting world of unicorn hunting and the ethical way to unicorn hunt in the swinger lifestyle. Kiley hosts the mind-blowing swinger podcast, where she's joined by the legendary TikTok and social media sensation swingerEd. Together, they unravel the secrets and pleasures ethical unicorn hunting and also get really candid about the OPP rule. For more info on Justin and Jess here’s their website with all the links https://...

Aug 18, 20231 hr 10 minSeason 1Ep. 34

33: Boundaries Explored: Navigating Swinging Boundaries with Lauren SwingingLifestyleCoach

Send us a text On this episode listen as Kiley and Lauren give you a thought-provoking and enlightening podcast episode. Join us as we delve into the intimate world of relationships, exploring the importance of establishing and navigating boundaries within the context of alternative lifestyles, but mainly swinging. In this groundbreaking podcast interview, Lauren brings her extensive experience in the swinging community to the forefront, offering valuable insights, practical advice, and real-lif...

Aug 11, 20231 hr 21 minSeason 1Ep. 33

32: Swinger Event Review: Naughty in N'awlins 2023 Part 2

Send us a text 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.thenonmonogamycar...

Aug 04, 20231 hr

31: Swinger Review Naughty N'awlins Part 1

Send us a text On this episode of the Pineapple Express podcast we talk about the first half of Naughty in Nawlins and all our fun sexy wild adventures at this once in a lifetime event. New to the lifestyle? Or need a relationship coach? ⤵️ https://www.expansiveconnection.com/workingwithus Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs •Secrets Hideaway Resort and Spa September 21-24 with The Swinger Society https://swingersociety.net •Play Champagne Halloween Freak Show Hotel ...

Jul 28, 202342 minSeason 1Ep. 31

30: Swinger Club Review: Colette New Orleans and Kiley dances on Bourbon Street

Send us a text On this episode of the Pineapple Express podcast we talk about our adventures in New Orleans with the Life of Spices and Kiley dances on Bourbon street. We talk about some new friends we made and our spicy night at Colette New Orleans. New to the lifestyle? Or need a relationship coach? ⤵️ https://www.expansiveconnection.com/workingwithus Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs •Secrets Hideaway Resort and Spa September 21-24 with The Swinger Society https...

Jul 21, 202352 minSeason 1Ep. 30

29: The Day of Visibility for Ethical Non Monogamy with Brett from OPEN

Send us a text 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.thenonmonogamycar...

Jun 30, 20231 hr 2 minSeason 1Ep. 29

28: Swinger Talk 'Dealing with Rejection in the Swinger Lifestyle'

Send us a text On this episode of “The Pineapple Express Podcast” Kiley talks about dealing with and responding to rejection in the Swinger Lifestyle. She has an in depth conversation and gives tips and tricks on how to respond to rejection. Do you have a lot of feelings? Dealing with jealousy? Rejection? All things non monogamy? If you are in need of some relationship coaching for swinging and non monogamy make sure you reach out to expansive connection. https://www.expansiveconnection.com/work...

Jun 16, 202347 minSeason 1Ep. 28

27: Swinger Club Review TPC North Houston and Colettes Houston

Send us a text On this episode of “The Pineapple Express Podcast” Kiley talks about her experiences at TPC Houston and Colette’s in Houston. Kiley talks about the ENM Summit with NCSF that she did in Houston and even gets choked up talking about her experiences with some of her hero’s and mentors. Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs Collettes New Orleans Red White and Blue 4th of July Party July 1 with Life of Spice and Dj Life of Spice https://coletteclubs.com •Naug...

Jun 02, 202345 minSeason 1Ep. 27

26: Swinger Talk with Mars and MingMing

Send us a text In this episode Kiley and Brad talk with Mars and MingMing in their first LIVE podcast at Play Champagne in Columbus Ohio. They talk about the BDSM lifestyle, consent and share some pretty fun and interesting stories about the Swinger lifestyle. Discord: https://discord.gg/swingersociety Vote for me on the ASN Lifestyle Awards for Best Content Creator, Best Social Media Influencer and Best Educator https://www.asnlifestylemagazineawards.com/nominations If you like this podcast lea...

May 26, 202358 minSeason 1Ep. 25

25: 'The Evolution Of Swinging' with guest host BostonSwingerKing

Send us a text In this episode Kiley and guest host Joe talk about their evolution with swinging. Join in on their very candid, unfiltered conversation about being swingers in 2023. Find Joe on Instagram at https://instagram.com/bostonkingandqueen?igshid=MzRlODBiNWFlZA== Collettes New Orleans Red White and Blue 4th of July Party July 1 with Life of Spice and Dj Life of Spice https://coletteclubs.com •Naughty in N’awlins July 5-9 with The Swinger Society and Play Champagne https://members.naughty...

May 19, 20231 hr 56 minSeason 1Ep. 25
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