Gypsy and a Gentleman

Rick & Gypsy

Intrigued and sexually charged with the thought of getting naughty with other like-minded people, Rick and Gypsy tread water as they transition into a non-monogamous marriage. Follow along as their sexual adventures and misadventures prove to be comical, sexy, silly, and disastrous, but never dull. Listen as they learn more about each other, grow together, and experience how amazing the swinging lifestyle can be while having sex with friends and strangers! Disclaimer: Listeners must be over 18. Information provided by the Gypsy & A Gentleman Podcast is for general entertainment purposes only. We make no claims regarding the accuracy, adequacy, validity, reliability, availability or completeness of any information presented. We do not provide medical, legal or psychological advice. Under no circumstances shall we have any liability for any loss or damage of any kind as a result of reliance on any information provided by this podcast. The content of this podcast belongs to Gypsy & A Gentleman and is covered by US Copyright law. Users may not copy or reproduce content without permission. The opinions expressed by the hosts of Gypsy & A Gentleman are solely our own and do not reflect the views of any other entity. Email: RG@gypsyandagentleman.com read less

Health & FitnessHealth & Fitness

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How to Survive Shutter Island as a Swinger

How to Survive Shutter Island as a Swinger

In this episode we talk about where we've been for the past 6 months, which may or may not include a stint on Shutter Island, or somewhere else just as uncomfortable. We lay it all on the line with complete transparency. Join us on yet another misadventure, this time does not include other people's genitalia. Think Shawshank Redemption meets Shutter Island meets an old folks home.

Episodes

How to Survive Shutter Island as a Swinger

How to Survive Shutter Island as a Swinger

In this episode we talk about where we've been for the past 6 months, which may or may not include a stint on Shutter Island, or somewhere else just as uncomfortable. We lay it all on the line with complete transparency. Join us on yet another misadventure, this time does not include other people's genitalia. Think Shawshank Redemption meets Shutter Island meets an old folks home.

How We Made Friends out of Swingers Instead of Swingers out of Friends!

How We Made Friends out of Swingers Instead of Swingers out of Friends!

This is kind of like a bonus episode we were hoping to get out during Summer Bang. But it didn't work out that way. After returning from Antigua and needing to consolidate and organize our thoughts about Summer Bang, we thought we'd discuss a sexy playtime we recently had with a couple we have been "courting" for almost a year. But this tantalizing tale is not just about sex, but also about how we befriended a lifestyle couple who are not only good friends now, but also hot lovers! Join us for a quick down and dirty episode. Stick around to the end for a small taste of Antigua. Flirtation is sold out already, but there is a wait list. Get on the waitlist for FLIRTation here - https://room77life.com/events77-mexico-feb-2023/ Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!And remember to keep having sex with strangers! - G&G

How to Communicate Expectations Before a Naughty Vacay!

How to Communicate Expectations Before a Naughty Vacay!

On today's episode we are joined by a couple who will be attending Summer Bang in Antigua, which is only 7 days away! This will be their first lifestyle event takeover, and we're so happy they've chosen Room 77 as ushers into an amazing journey. We talk about comfort levels, fears, expectations, and even discuss zombie pirate hookers, cuz you never know when the apocalypse will strike. Join us for a fun discussion with new friends! Book your FLIRTation spot here - https://room77life.com/events77-mexico-feb-2023/ Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!And remember to keep having sex with strangers! - G&G

What to Expect at a Lifestyle Hotel Takeover

What to Expect at a Lifestyle Hotel Takeover

We are joined today by "world renowned lifestyle event planner and professional swinger," Cat Stone. The topic of discussion? Event takeover preparedness. The lifestyle season is in full swing (see what I did there), and it never hurts to be ready at the drop of a hat or even if you have 6 months to plan for your next trip. Physical, mental and emotional preparedness is critical for optimizing your enjoyment with your partner while on a LS vacay. In this episode we're covering all things takeover, from what to pack in our suitcases, to the mental baggage we all wish we could leave unattended at the airport. If this is your first lifestyle event or 50th, we think it covers quite a bit and will in some way resonate with all. Truly hope you all enjoy! Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!And remember to keep having sex with strangers! - G&G

How to Get from Cocktails to Hotels

How to Get from Cocktails to Hotels

This past month has been riddled with dates with multiple couples. All were successfully fun, but one in particular had a happy ending, sort of. In this episode we discuss the successes of our multiple dates. While Gypsy encounters a quite large surprise , Rick has to have a serious heart to heart discussion with his *ehem* other head. Join us on yet another adventure, or misadventure in the lifestyle as we tackle a topic that may or may not be common in the swinging community. Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email us at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!

How to Have a Threesome While Waiting for Pizza Delivery

How to Have a Threesome While Waiting for Pizza Delivery

Gypsy becomes a sex broker and grade "A" top choice wingman by setting up a playdate for Rick while he was away from home traveling. He breaks down all the details on how it went down, which includes comical scenes that can only come from Rick's awkward inexperience in the LS. Gypsy's redemption song of sensual moans leads to another hot and heavy encounter in the recording studio. Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email us at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!

How To Get Naked in Front of Strangers for the First Time

How To Get Naked in Front of Strangers for the First Time

Rick and Gypsy have been breaking headboards since 2008, but struggle with getting to the big show (play sessions) with strangers. They prepare for their first hotel takeover by going to a local nude resort where they witness a poolside finger banging for the first time, and then they put on a show for another couple in the playroom. Finally they talk about their first experience at a hotel takeover and all the awkwardness being social/flirty is for for them. Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email us at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!

How To Navigate Dating Sites and Belly Flop on Your First Date.

How To Navigate Dating Sites and Belly Flop on Your First Date.

Rick and Gypsy have sex with their neighbors and Rick finds the lifestyle while binge researching how to have sex with strangers. Together they navigate a lifestyle dating website and discuss their first date, which ends in tragedy (self-inflicted). They also talk about how whorish they can be while trying to meet other couples. We also get to see their reaction when they encounter a flaky couple who vanish into thin air after 6 months of talking.Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email us at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!

How To Write Sex Commandments - aka Setting Boundaries

How To Write Sex Commandments - aka Setting Boundaries

Rick and Gypsy discuss sexual boundaries and in hindsight, should have had this conversation a year ago. Rick discusses the appeal of a threesome while Gypsy goes down on him, and Gypsy does the same while Rick takes her from behind. Come hang out with us over on Twitter! @GypsyAndAGent Questions? Comments? Send us an email us at RG@gypsyandagentleman.comWe'd love to hear from you! Thanks for listening!