The Pineapple Express: A Millennial’s Guide to Love, Sex Positivity, Non-Monogamy, Polyamory & Swinging
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 connectionEach 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.
Latest episodes
Dec 22, 2023 • 1h 1min
46: The Nuances Of being a Cuckquean with Kink and Intimacy Coach Julieta
Send us a textThe 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=PAAaYDAFDK1Tou7rXLBYWheYVdUZ2bbnuN6hCIbTDVpAVDRTUR56jsYxXjTNE_aem_AZtzbvFy703dLUfE4E1jpvvaNIh5MhxHBhKRwXv1gIB-mIagyjLI4Syv8tDOwa_52KEMy 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://cluberoscleveland.comEmail us at:Kileyg1991@gmail.com Onlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. For more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gVSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Dec 15, 2023 • 54min
45: Relationship Anarchy with Annie Undone
Send us a textMeet 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-anarchyTo learn more about Annie Undone and all the amazing things they are doing in this world here is a link to their website https://annieundone.com/?fbclid=PAAaalFa2plUGg4Ja1ksWBnjVUAudQXJ-YhuCg4H5KNlzMywmx1VfA36k7xBI_aem_AWvl4QSLuVB3xk8xYw6pA2jg0wrfzEvtPu3xBPNSL9hrmFE0KUcPYTgLk9MSlxpSJ4gMy 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://cluberoscleveland.comEmail us at:Kileyg1991@gmail.com Onlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. For more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Nov 24, 2023 • 57min
44: Non Monogamy and Spirituality With Clara from Conscious Polyamory
Send us a textMeet Clara from Conscious Polyamory Resources Teachings on Love, by Thich Nhat Hanh https://amzn.to/40XtymaWhen things fall apart, by Pema Chodronhttps://amzn.to/47tjhR4Spiritual Polyamory https://amzn.to/3SWXNrbConscious 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://cluberoscleveland.comEmail us at:Kileyg1991@gmail.com Onlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. For more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:https://discord.gg/swingersocietySponsor Links:https://swingersociety.Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Nov 17, 2023 • 38min
43: Swinger Talk: Being Grateful for your partner and Non Monogamy and Swinging
Send us a textMy coaching website is LIVE https://www.consciousloveconnectioncoach.com/Swinger Websites : SDC Kasidie https://theswingnation.info/?fbclid=PAAaYO8_1ww28dTbwC3Er2SAU5vVTlx03z8GlHhRKMdIDrbdcfCgnNnYfqDRA_aem_AeXcQC8qqYgu9PP6dqg_ely-fVnpo9L6-uLCZw5t48pki8IFoQ35pgiER-SSaFvHnhYSLS https://www.swinglifestyle.com/3fun https://www.go3fun.co/ad/TK10098Club Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. For more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:https://discord.gg/swingersocietySponsor Links:https://swingersociety.net/https://www.go3fun.co/ad/TK10098Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Nov 10, 2023 • 44min
42: Swinger Education: How to Join The Swinger Lifestyle And Find Success As A Single Male
Send us a textSwinger Websites : SDC Kasidie https://theswingnation.info/?fbclid=PAAaYO8_1ww28dTbwC3Er2SAU5vVTlx03z8GlHhRKMdIDrbdcfCgnNnYfqDRA_aem_AeXcQC8qqYgu9PP6dqg_ely-fVnpo9L6-uLCZw5t48pki8IFoQ35pgiER-SSaFvHnhYSLS https://www.swinglifestyle.com/3fun https://www.go3fun.co/ad/TK10098Club Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. OUR NEW WEBSITE IS LIVE https://kileyg1991.wixsite.com/mysiteDon’t forget to sign up for our newsletter and stay up to date on All Things Pineapple Express http://eepurl.com/immxdIFor more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:https://discord.gg/swingersocietySponsor Links:Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Nov 3, 2023 • 1h 12min
41: Let’s Talk About Swinging: How to approach your partner about joining the Swinger Lifestyle with Swinger Lifestyle Coach Lauren
Send us a textWelcome 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_6FTDmupHGFTsKCSHlZN2USMLAUxQeRHveg9iOwTnHHXtcfyU4-UClub Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. OUR NEW WEBSITE IS LIVE https://kileyg1991.wixsite.com/mysiteDon’t forget to sign up for our newsletter and stay up to date on All Things Pineapple Express http://eepurl.com/immxdIFor more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Oct 27, 2023 • 56min
40: Swinger Education 'Tips for dealing with jealousy and insecurity in Non Monogamy' with Professor Playtime
Send us a textOn 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-monogamy to explore these complex emotions, develop healthy coping mechanisms, and foster fulfilling connections within the swinger community.For more info on Bridget aka professor playtime from For Love find her here https://allmylinks.com/forloveTo join Bridget and OPEN in their monthly peer support groups specializing in non monogamous relationship structures sign up here https://www.open-love.org/rsvp/peersupport101Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs•Club Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. OUR NEW WEBSITE IS LIVE https://kileyg1991.wixsite.com/mysiteDon’t forget to sign up for our newsletter and stay up to date on All Things Pineapple Express http://eepurl.com/immxdIFor more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Oct 20, 2023 • 59min
39: Swinger Horror Stories With BostonSwingerKing
Send us a textJoin 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/bostonswingerqueenOpen-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs•Club Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. OUR NEW WEBSITE IS LIVE https://kileyg1991.wixsite.com/mysiteDon’t forget to sign up for our newsletter and stay up to date on All Things Pineapple Express http://eepurl.com/immxdIFor more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:https://discord.gg/swingersocietySponsor Links:https://swingeSupport the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Oct 13, 2023 • 1h 52min
38: Swinger Event Review: Secrets "A Weekend To Remember" With BostonSwingerKing
Send us a textJoin 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/bostonswingerqueenOpen-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xs•Club Eros CLEVELAND https://cluberoscleveland.comEmail us at: thepineappleexpresspodcast@gmail.comOnlyfans https://onlyfans.com/sexyswingerchicDiscord:https://discord.gg/swingersocietyIf you like this podcast leave us a review to let other listeners know what you like we are always looking to improve what we can do for you. OUR NEW WEBSITE IS LIVE https://kileyg1991.wixsite.com/mysiteDon’t forget to sign up for our newsletter and stay up to date on All Things Pineapple Express http://eepurl.com/immxdIFor more info about me and where to find all the events we will be at and to get an exclusive invite to The Swinger Society Discord make sure you check out my website https://sexyswingerchic.net/I’m on clapper so if TikTok gets banned follow me here: https://clapperapp.com/Sexyswingerchic?is_invite=1&r=gV6ALln5op&c=in&m=coJoin the Discord:https://discord.Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
Sep 8, 2023 • 1h 39min
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 conversation that will empower and inform swingers and non-swingers alike.Open-A Journey Through Love Preview https://youtu.be/5Rwb5-SZ_xsFor more information on NCSF click this link https://linktr.ee/ncsfreedom?fbclid=PAAaaCuV_9s9UFXBOxGEJ3J_Ohj1q_2XBxTrOP0jCQiaAJpMvBJEiQMnlDm78_aem_Abgmp0Gx4_sbF8Tuu8NyXnlQW_PGZC90b9Eqb1SDQtcE3W3TqitycPA9FSSCnBaOrtA•Secrets Hideaway Resort and Spa September 21-24 with The Swinger Society overflow hotels for 'A Weekend To Remember' https://www.google.com/travel/search?q=kissimee%20hotels&g2lb=2502548%2C2503771%Support the show🎙️ The Pineapple Express PodcastSubscribe 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 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 updates, insights, and inspiration: Instagram:@Thepineappleexpresspodca...
