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Ruby Ryder – Pegging Paradise

ByRuby Ryder
50 episodes

Podcast Summary

Dive into "Ruby Ryder – Pegging Paradise," the podcast that unravels the intricacies of pegging, anal sex, and BDSM with a refreshing candidness. Each episode features intimate conversations with thought leaders and influencers from the sexual wellness community, exploring diverse perspectives and experiences. From renowned sex educators discussing the importance of consent and communication to authors sharing their personal journeys of sexual exploration, the show creates a safe space for curiosity and learning. Unique to "Pegging Paradise" is its blend of humor and education, making complex topics accessible and engaging. Ruby Ryder’s warm and inviting hosting style invites listeners to embrace their desires without shame. Recent episodes have featured discussions on the dynamics of dominant/submissive relationships and the evolving landscape of sexual pleasure. Whether you're a novice or a seasoned explorer, this podcast offers valuable insights to enhance your journey into uncharted territories of intimacy. Tune in and discover a paradise of pleasure!

#1

Short Takes on Power Bottoming, and How to Reignite the Spark

Welcome to another Short Take! This one has a couple of shares. The first is about dominant/submissive challenges with pegging - power bottoming and how it improved one couple's pegging dynamic. The second is asking for ideas to reignite the sexual spark after 24 years of marriage. Enjoy! And just in case you missed it […] The post Short Takes on Power Bottoming, and How to Reignite the Spark appeared first on Ruby Ryder - Pegging Paradise.

2025-05-24•13mins
#2

Short Take On Masculine Surrender and Virginity

Sunday 1/19 is my next Virtual Happy Hour! Register Here. A couple of letters for you today! Masculine surrender and vulnerability and so-called 'virginity'. I do believe that there is healing potential in anal penetration for all prostate owners, but especially for the intensely masculine receivers. Allowing a bit of feminine in to help find […] The post Short Take On Masculine Surrender and Virginity appeared first on Ruby Ryder - Pegging Paradise.

2025-01-19•13mins
#3

Short Take on Feeling Clingy, Depth Injuries, and Condoms

Feeling Clingy, Depth Injuries, and Condoms! Articles and Information In this short take you will find an attempt at crowdsourcing for a gentleman who had a depth play injury at the rectosigmoid junction. He also had a horrible experience with an MD who couldn't get beyond his own discomfort to give good care. Next, she […] The post Short Take on Feeling Clingy, Depth Injuries, and Condoms appeared first on Ruby Ryder - Pegging Paradise.

2024-12-29•20mins
#4

Short Take – What to Say and Big Toy Questions

Articles/Information Equipment Webinar Sale is ON - Limited Time Offer All 3 of my Webinars - the Premium Pegging Package - are now on sale until the end of the year, discounted from $99 to $75! This enables you to have a six hour complete educational pegging library on hand for new partners, additional partners, […] The post Short Take – What to Say and Big Toy Questions appeared first on Ruby Ryder - Pegging Paradise.

2024-12-15•21mins
#5

Short Take on the Initial Insertion

Initial Insertion Short Take Jessica's question is common for new Givers. She's concerned about getting the toy in so the fun can begin! Initial insertion doesn't need to be unpleasant for the receiver. For the giver, when you take the right steps to open up the ass, initial insertion goes more smoothly. This can give […] The post Short Take on the Initial Insertion appeared first on Ruby Ryder - Pegging Paradise.

2024-12-05•11mins
#6

Podcast #303 Pops Right Up!

Pegging Paradise Podcast Just when you wondered if you'd lost me... Another podcast pops right up! Information/Articles Equipment I hope you enjoy this podcast. Speaking of something that pops right up, there are two inflatable toys for you to check out this time! One from my last blog post, The Strap On Me Inflatable, […] The post Podcast Pops Right Up! appeared first on Ruby Ryder - Pegging Paradise.

2024-02-14•53mins
#7

“I Love Seeing You Like This” – Podcast #302

"I love seeing you like this." My interviewee, Steve, has heard these words many times while receiving pegging from his partner. We hear Steve's story about how he began walking down the path of pegging and how his experience has evolved over the years. He speaks eloquently about what he loves about pegging, and his […] The post “I Love Seeing You Like This” – Podcast appeared first on Ruby Ryder - Pegging Paradise.

2023-10-16•1hr 13mins
#8

Turning the Spotlight on Podcast #301

Pegging Paradise Podcast Information/Articles Equipment I hope you enjoy podcast ! I included a link to an instagram video from Joe Kort that relates to my new article posted on 7/2, "Men Like to Feel Beautiful and Wanted, Too". There's a lot to this line of thinking. I think the reasons that women are […] The post Turning the Spotlight on Podcast appeared first on Ruby Ryder - Pegging Paradise.

2023-08-18•57mins

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#9

How to Be More Dominant While Pegging Your Partner

More dominant, please - the thought going through many receivers minds. The magic of Pegging, in my opinion, is that it is a customizable sexual activity. Pegging can look many different ways depending on the desires and leanings of the people involved. One couple might enjoy a sensual, love-making experience while another might prefer a […] The post How to Be More Dominant While Pegging Your Partner appeared first on Ruby Ryder - Pegging Paradise.

2023-07-10•11mins
#10

Here it is! Presenting Podcast #300 Part Two!

Podcast Part 2, where Michelle and I continue the conversation talking about responsive desire, celebrating people's no, and more. We explore touch, awakening the prostate, foreplay in solo anal exploration, and giving yourself permission. And don't forget, Soft Cock Week is coming again November 5 - 11, 2023! There are so many subjects around […] The post Here it is! Presenting Podcast Part Two! appeared first on Ruby Ryder - Pegging Paradise.

2023-07-09•51mins
#11

This is it! Presenting Podcast #300 Part One!

Presenting Podcast ! I am joined by Michelle Rene, sexual surrogate, sex worker, intimacy guide, human connection coach and creator of Soft Cock Week. We talk about many. many things. You will surely find some nuggets in there for yourself. Thanks for listening! Articles/Information Pegging Gangbang Interview Part OnePegging Gangbang Interview Part TwoPodcast […] The post This is it! Presenting Podcast Part One! appeared first on Ruby Ryder - Pegging Paradise.

2023-07-09•1hr 7mins
#12

Get Down and Get Funky With Podcast #299

Pegging Paradise Podcast Articles/Information Equipment Podcast touches on a variety of different topics until finally revisiting that question of a fucking machine, but this time it is not a machine, it's a rocker. We've talked about these before and since that time there's a new upgrade to the plans, if you are a […] The post Get Down and Get Funky With Podcast appeared first on Ruby Ryder - Pegging Paradise.

2023-06-11•1hr 8mins
#13

Celebrations and Inquiries – Podcast #298

Pegging Paradise Podcast Articles/Information Equipment Podcast contains some great stories about this journey we call pegging, from beginning anal play to the real deal. I never tire of hearing how that story unfolds, the challenges and thrills along the way. The recurring theme so often seems to be the deep satisfaction of being […] The post Celebrations and Inquiries – Podcast appeared first on Ruby Ryder - Pegging Paradise.

2023-04-07•46mins
#14

Surprise! Podcast #297 Appears!

Podcast brings all kinds of good things, like putting on a show for your partner, thinking hard about the connection of bisexuality and pegging, and a deep dive (pun intended) into lube options. PLUS, I finally found a lube option for you wide toy aficionados that measures up to my lube snob standards - […] The post Surprise! Podcast Appears! appeared first on Ruby Ryder - Pegging Paradise.

2023-03-20•1hr 2mins
#15

Podcast #296 Interview with Zach Budd

Pegging Paradise Podcast My interview with Zach Budd, and his reflections on consent, anal receptive play, and where the two meet, are an interesting listen. The journey he took that led him to take a deep dive into exactly what consent means in our world is fascinating. We discuss why guerilla ass play and […] The post Podcast Interview with Zach Budd appeared first on Ruby Ryder - Pegging Paradise.

2022-12-01•1hr 8mins
#16

Podcast #295 It’s Not Hard!

Listen to Pegging Paradise Podcast Podcast is my offering to Soft Cock Appreciation Week, the brainchild of Michelle Renee at HumanConnectionCoach.com. For too long, there has been far too much emphasis on erections, how to get them, what to do if you don't have one, and pretty much everything that surrounds the constant […] The post Podcast It’s Not Hard! appeared first on Ruby Ryder - Pegging Paradise.

2022-11-11•47mins
#17

Podcast #294 Lex Shares About BIG Toys

Pegging Paradise Podcast My Interview with Lex, IMO an expert on longer and wider toys. With his background of product designer, engineering, artistic creativity, constant curiosity and a large dose of chemical and physical science, Lex takes us on a very deep dive (pun intended) into this more extreme toy play. This podcast is […] The post Podcast Lex Shares About BIG Toys appeared first on Ruby Ryder - Pegging Paradise.

2022-10-27•1hr 40mins
#18

Tickle Your Ears with Podcast #293

Podcast - for your listening pleasure! He describes his sexual assault (trigger warning) Short and sweet happy news! He loves feminization and she's concerned He introduces us to the 'Peg Pal' term! Pegging Celebration Time! They pegged before, but not for a while. This time was amazing! Pegging Celebration Time! New relationship and pegging […] The post Tickle Your Ears with Podcast appeared first on Ruby Ryder - Pegging Paradise.

2022-09-22•49mins
#19

An Auditory Delight! Podcast #292

Listen to Pegging Paradise Podcast ! Podcast brings you new toys, discussion about dominant and submissive labels, and much more! Ruby discusses Sexual Dominance, Submission and Labels Response to ED/age issues from Response to wanting to feel pretty His story about bisexuality and pegging with his wife He wants his wife to […] The post An Auditory Delight! Podcast appeared first on Ruby Ryder - Pegging Paradise.

2022-07-31•1hr 3mins
#20

Podcast #291 Rolls Into Town

Podcast Rolls Into Town! So - Some great stuff with this podcast. My fascination with vulnerability continues. So I gathered together a number of shares about the emotional vulnerability felt by receivers during pegging. And then we have a celebration, too! To begin with, more suggestions for incorporating pain with pegging Pegging after a […] The post Podcast Rolls Into Town appeared first on Ruby Ryder - Pegging Paradise.

2022-06-01•52mins
#21

Podcast #290 Steps Onto the Stage!

Letter from an appreciative Patron He struggles with shame due to pegging She wants to satisfy his desire for masochism during pegging He loves the anticipation and looking sexy for his partner He shares about letting go of the past and asking for anal play Pegging Celebration Time! Same couple! He shares their story Pegging […] The post Podcast Steps Onto the Stage! appeared first on Ruby Ryder - Pegging Paradise.

2022-04-22•1hr 0mins
#22

Podcast #289 is in the Room!

Listen to Pegging Paradise Podcast No butts in the USA He discovers about real trust with pegging New to pegging but not solo play, he has size questions He lets go of the shame and guilt, and talks to his wife He has some questions about vibe vs no vibe She seeks a toy […] The post Podcast is in the Room! appeared first on Ruby Ryder - Pegging Paradise.

2022-03-23•31mins
#23

Lend an Ear to Podcast #288

For your listening pleasure - it is indeed time to... Lend an Ear to Podcast ! She offers more info re: chastity, cuckolding & humiliation questions He noticed men's clothing ads in the US don't show asses - WTF? Podcast Story - He mustered the courage and she was receptive! From - He […] The post Lend an Ear to Podcast appeared first on Ruby Ryder - Pegging Paradise.

2022-03-12•27mins

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#24

Podcast #287 Greets the New Year!

Podcast Greets the New Year! He sends fan mail! Encouraging pegging with his wife plus CD and ED issues He has lube and harness questions He has questions about the angle of toy vs rectum She checks in 5 yrs later on pegging, chastity & cuckolding He can relate to the term 'Man Box' […] The post Podcast Greets the New Year! appeared first on Ruby Ryder - Pegging Paradise.

2022-02-01•59mins
#25

Podcast #112 – The Introduction

Podcast for the Givers The Introduction The introduction of the concept of pegging is the hardest part for most hopeful receivers. Broaching the subject with their partner often requires courage and communication. That's exactly the situation that this podcast was created for. Since podcast has gotten so much air time - I am […] The post Podcast – The Introduction appeared first on Ruby Ryder - Pegging Paradise.

2022-01-28•51mins
#26

Podcast #286 Completes 2021!

Podcast completes 2021 with style! Enjoy the pegging celebration stories, and everything else this episode has to offer. Happy New Year! Movember ends with Bodacious Tatas! New Article - Stigma of Big Toys Comment on ED issues from Pegging Celebration Time! Beatrice & Dante do the deed a month after interviewing me! He […] The post Podcast Completes 2021! appeared first on Ruby Ryder - Pegging Paradise.

2021-12-31•41mins
#27

Movember Ushers in Podcast #285

Pegging Paradise Podcast Movember Ushers in... Trigger Warning: talk of suicide Movember ushers in thoughts of masculinity, mean's health, men's mental health and the Movember Foundation! This podcast is full of personal shares from men who have struggled with mental health, suicide, and life's hardships. They share with us stories of how they coped, […] The post Movember Ushers in Podcast appeared first on Ruby Ryder - Pegging Paradise.

2021-11-10•39mins
#28

Into Your Mailbox Falls Podcast #284

Into your mailbox and straight to your ears? Are you one of those people who gets your notification that a podcast was delivered into your mailbox, and you immediately queue it up? Or do you save them to savor later? Either way...enjoy! For Your Listening Pleasure The clips/gifs/photos I send to patrons offer him an […] The post Into Your Mailbox Falls Podcast appeared first on Ruby Ryder - Pegging Paradise.

2021-10-25•50mins
#29

Presenting Podcast #283

Pegging Paradise Podcast Presenting Podcast for your listening pleasure! He wants to be slut shamed; she needs suggestions He masturbated with anal play in front of her, and has feels about it Trying to get his wife on board with pegging He's having trouble with penetration about 3-4 inches in He's curious about […] The post Presenting Podcast appeared first on Ruby Ryder - Pegging Paradise.

2021-10-16•47mins
#30

Podcast #282 – Have Issues, Want Advice

Pegging Paradise Podcast Want advice - When he asks for what he wants, she shuts him down She struggles with self-confidence and the learning curve He speaks eloquently about opening up and submission She understands her husband more after reading my story He wonders if pegging encourages cuckolding? Articles/Information Janet Hardy - The Sexually […] The post Podcast – Have Issues, Want Advice appeared first on Ruby Ryder - Pegging Paradise.

2021-09-21•43mins
#31

Podcast #281 Pops Up Like Magic!

Pegging Paradise Podcast Ruby shares a few (more) thoughts on Pegging and Orientation Relax, Respond, and React got him to his first HFO! She shares her views on what makes a good bottom! He's on his butt path, pegging will happen soon, & she's excited! He lets go of his shame, is honest with […] The post Podcast Pops Up Like Magic! appeared first on Ruby Ryder - Pegging Paradise.

2021-09-11•30mins
#32

#280 – The Need For Receiver Aftercare

Pegging Paradise Podcast The need for receiver aftercare and what it can look like He's a newbie at prostate stimulation. First time kind of freaked him out. We all just want to be loved and accepted Articles and Information Tony Porter - A Call to Men Tony Porter - The Roles Men Play Podcast […] The post – The Need For Receiver Aftercare appeared first on Ruby Ryder - Pegging Paradise.

2021-09-03•38mins
#33

Podcast #279 – Challenges for the Old Folks!

Articles/Information Equipment The post Podcast – Challenges for the Old Folks! appeared first on Ruby Ryder - Pegging Paradise.

2021-07-25•39mins
#34

Podcast #278 – On Being a Good Bottom

Givers! I would love to hear from you - In your pegging world, what makes a good bottom? Of course it's very individual for each giver and each couple. So tell me, what does your receiver do/not do to make your pegging experience most enjoyable? In this episode I talk about what I like, as […] The post Podcast – On Being a Good Bottom appeared first on Ruby Ryder - Pegging Paradise.

2021-07-23•33mins
#35

Oh Boy! Pegging Paradise Podcast #277 is Here!

Pegging Paradise Podcast Pegging Celebration Time! Communication was key. He tells their long story! She wonders what the clear liquid from her partner is? She shares some helpful resources of their path to pegging They are inspired by the long story request, and tell theirs! He is courageous, tells his wife about sucking the […] The post Oh Boy! Pegging Paradise Podcast is Here! appeared first on Ruby Ryder - Pegging Paradise.

2021-04-29•56mins
#36

Pegging Paradise #276 Has Arrived!

Pegging Paradise Podcast His solo anal play now involves his wife, but still no pegging, help? She's feeling very left out with his newfound love of pegging He's concerned about large girth toys and potential damage He waxes poetic about his sex life and has a few questions, too! He seeks information about lubes […] The post Pegging Paradise Has Arrived! appeared first on Ruby Ryder - Pegging Paradise.

2021-03-29•1hr 9mins
#37

Yay! Podcast #275 is Here For You!

Pegging Paradise Podcast Photo credit - PrettyDomme FetLife: Only Fans: Pegging Celebration Time! His first time causes a loss of his faculties! He wants pegging. She doesn't. He wants pegging. Her, not so much. Their Strap On Me Double and Joque have issues He wants pegging. She doesn't want to see him […] The post Yay! Podcast is Here For You! appeared first on Ruby Ryder - Pegging Paradise.

2021-03-12•51mins
#38

Great News! It’s Podcast #274!

Pegging Paradise Podcast - Great News! Articles/Info Equipment Pegging Paradise Podcast - Great News! The post Great News! It’s Podcast ! appeared first on Ruby Ryder - Pegging Paradise.

2021-02-26•53mins
#39

A Delightful Listen! Podcast #273

I'm on Tiktok! He's seeking harness guidance He votes for listeners' whole (long) stories! She'd love some new newbie guidance He has equipment questions He enjoys dominant pegging with a little pain - it that healthy? He's got some questions about finding his prostate They love pegging & want to add dominance & submission Articles/Information […] The post A Delightful Listen! Podcast appeared first on Ruby Ryder - Pegging Paradise.

2021-02-18•51mins
#40

Pegging Paradise Podcast #272

More input about ED after initial pegging Great description of prostate orgasm vs penile orgasm He shares the story of how they finally got to pegging He writes back with details of their first time! He reflects on their pegging, eloquently Pegging Celebration Time! She conquers her concerns, tries pegging and LOVES it He wants […] The post Pegging Paradise Podcast appeared first on Ruby Ryder - Pegging Paradise.

2021-01-11•1hr 5mins
#41

Pegging Paradise Podcast #271 Part 2

Recap of Movember Mr. Hankey's Sale Pandemic Reflections New Strap On Me Harnesses! Hot Octopuss Pulse III Duo Nexus B-Stroker Plug She shares thoughts about her love of pegging Searching for a dildo that will insert her squirt! His personal experience and advice about huge toys They are searching for harnesses for XXL toys After […] The post Pegging Paradise Podcast Part 2 appeared first on Ruby Ryder - Pegging Paradise.

2020-12-06•38mins
#42

Pegging Paradise Podcast #271 Part 1

Recap of Movember Mr. Hankey's Sale Pandemic Reflections New Strap On Me Harnesses! Hot Octopuss Pulse III Duo Nexus B-Stroker Plug She shares thoughts about her love of pegging Searching for a dildo that will insert her squirt! His personal experience and advice about huge toys They are searching for harnesses for XXL toys After […] The post Pegging Paradise Podcast Part 1 appeared first on Ruby Ryder - Pegging Paradise.

2020-12-06•44mins
#43

Pegging Paradise Podcast #270

Movember Link to Donate How I Teach Webinars The Man Box My story about Frank My first awareness of the Man Box An eloquent share about the Man Box What can Men do? What can Women do? Reading from The Little Book for Men Links for you - new Ted Talks! Articles/Information Movember Donation […] The post Pegging Paradise Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-11-26•1hr 6mins
#44

Pegging Paradise Podcast #269

Pegging Paradise Podcast He writes back with more thoughts about cum eating A Taste Tester shares his journey He takes it to the level of pre-cum in a shot glass! His story about coming to terms with his love of penetration He is shy to initiate and girlfriend doesn't want to schedule. Help? They […] The post Pegging Paradise Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-11-05•1hr 1mins
#45

Pegging Paradise Podcast #268

Listen to Pegging Paradise Podcast A reaction to Aussie Man's story () from another Aussie Man! His review of the We-Vibe Vector app-controlled Prostate massager My adventures with the We-Vibe Vector Pegging Celebration Time! They communicate, work through some stuff and it happens! Pegging Celebration Time! His sex life from losing his virginity to […] The post Pegging Paradise Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-10-26•1hr 4mins
#46

Pegging Paradise Podcast #267

Listen to Pegging Paradise Podcast ! Articles/Information Equipment The post Pegging Paradise Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-10-06•1hr 5mins
#47

Pegging Paradise Podcast #266!

Listen to Pegging Paradise Podcast Pegging Celebration Time! He shares his story of their long, and finally successful, pegging journey He waxes poetic about men who like pegging not being gay Celt lass tells story of how she found her like-minded partner Pegging Celebration Time! Initiated in December, she gives him the best fucking […] The post Pegging Paradise Podcast ! appeared first on Ruby Ryder - Pegging Paradise.

2020-09-17•1hr 8mins
#48

Podcast #265

Listen to Pegging Paradise Podcast Response to Manly Man's Man letter (podcast ) Listener offers review of two toys!! (Godemiche Adam & Strap-On-Me Vibrating Double) He shares about pegging, with & without a prostate She feels betrayed by his lack of honesty about his butt plug He's having difficulty transitioning from 1.25" to 1.5" […] The post Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-08-19•1hr 5mins
#49

Podcast #264

Listen to Pegging Paradise Podcast Articles/Information Equipment The post Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-08-07•59mins
#50

Podcast #263

Listen to Pegging Paradise Podcast He experiences a Prostate Awakening! She does a 180 regarding pegging! He's beyond thrilled She tells the story of how she started pegging Manly man finds his fucking ass whore inside Toy questions for BBW during cowboy He wants to find reviews of toys by men who use them! […] The post Podcast appeared first on Ruby Ryder - Pegging Paradise.

2020-07-25•1hr 5mins

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