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Ruby Ryder – Pegging Paradise

English, Sex education, 1 season, 51 episodes, 1 day, 16 hours, 21 minutes
About
Pegging is a sexual practice in which a woman penetrates a man's anus with a strap-on dildo. Strap-on sex is a seductive, passionate option to add to your treasure chest of possibilities as a sexually adventurous couple or a sexually explorative single. This podcast explores the physical, emotional and psychological aspects of pegging. Pegging has the potential to be a powerful tool in revitalizing or adding spice to almost any relationship. Strap-on sex involves role reversal. The penetrator becomes the penetrated. The one usually receiving is giving. The one usually in control is not. All kinds of exciting and sometimes startling things happen as a result. Experience a deepening of intimacy by sexually taking a walk in your partner's shoes. We’ll cover information on how to talk with your partner, equipment information, tips on technique, getting past the myths and misconceptions, success stories and much, much more. If you have ever been fascinated by the thought of heterosexual strap-on play – this podcast is for you. Visit https://peggingparadise.com for a plethora of erotic pegging stories, photos and blog.
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“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 #302 appeared first on Ruby Ryder - Pegging Paradise.
10/16/20231 hour, 13 minutes, 48 seconds
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Turning the Spotlight on Podcast #301

Pegging Paradise Podcast #301 Information/Articles Equipment I hope you enjoy podcast #301! 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 #301 appeared first on Ruby Ryder - Pegging Paradise.
8/18/202357 minutes, 20 seconds
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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.
7/10/202311 minutes, 48 seconds
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Here it is! Presenting Podcast #300 Part Two!

Podcast #300 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 #300 Part Two! appeared first on Ruby Ryder - Pegging Paradise.
7/9/202351 minutes, 26 seconds
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This is it! Presenting Podcast #300 Part One!

Presenting Podcast #300! 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 #146 Part OnePegging Gangbang Interview #146 Part TwoPodcast […] The post This is it! Presenting Podcast #300 Part One! appeared first on Ruby Ryder - Pegging Paradise.
7/9/20231 hour, 7 minutes, 39 seconds
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Get Down and Get Funky With Podcast #299

Pegging Paradise Podcast #299 Articles/Information Equipment Podcast #299 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 #299 appeared first on Ruby Ryder - Pegging Paradise.
6/11/20231 hour, 8 minutes, 49 seconds
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Celebrations and Inquiries – Podcast #298

Pegging Paradise Podcast #298 Articles/Information Equipment Podcast #298 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 #298 appeared first on Ruby Ryder - Pegging Paradise.
4/7/202346 minutes, 49 seconds
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Surprise! Podcast #297 Appears!

Podcast #297 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 #297 Appears! appeared first on Ruby Ryder - Pegging Paradise.
3/20/20231 hour, 2 minutes, 45 seconds
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Podcast #296 Interview with Zach Budd

Pegging Paradise Podcast #296 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 #296 Interview with Zach Budd appeared first on Ruby Ryder - Pegging Paradise.
12/1/20221 hour, 8 minutes, 18 seconds
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Podcast #295 It’s Not Hard!

Listen to Pegging Paradise Podcast #295 Podcast #295 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 #295 It’s Not Hard! appeared first on Ruby Ryder - Pegging Paradise.
11/11/202247 minutes, 43 seconds
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Podcast #294 Lex Shares About BIG Toys

Pegging Paradise Podcast #294 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 #294 Lex Shares About BIG Toys appeared first on Ruby Ryder - Pegging Paradise.
10/27/20221 hour, 40 minutes, 41 seconds
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Tickle Your Ears with Podcast #293

Podcast #293 - 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 #293 appeared first on Ruby Ryder - Pegging Paradise.
9/22/202249 minutes, 4 seconds
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Podcast #291 Rolls Into Town

Podcast #291 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 #291 Rolls Into Town appeared first on Ruby Ryder - Pegging Paradise.
6/1/202252 minutes, 37 seconds
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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 #290 Steps Onto the Stage! appeared first on Ruby Ryder - Pegging Paradise.
4/22/20221 hour, 26 seconds
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Podcast #289 is in the Room!

Listen to Pegging Paradise Podcast #289 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 #289 is in the Room! appeared first on Ruby Ryder - Pegging Paradise.
3/23/202231 minutes, 4 seconds
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Lend an Ear to Podcast #288

For your listening pleasure - it is indeed time to... Lend an Ear to Podcast #288! She offers more info re: chastity, cuckolding & humiliation questions He noticed men's clothing ads in the US don't show asses - WTF? Podcast #112 Story - He mustered the courage and she was receptive! From #286 - He […] The post Lend an Ear to Podcast #288 appeared first on Ruby Ryder - Pegging Paradise.
3/12/202227 minutes, 44 seconds
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Podcast #287 Greets the New Year!

Podcast #287 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 #287 Greets the New Year! appeared first on Ruby Ryder - Pegging Paradise.
2/1/202259 minutes, 13 seconds
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Podcast #112 – The Introduction

Podcast #112 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 #112 has gotten so much air time - I am […] The post Podcast #112 – The Introduction appeared first on Ruby Ryder - Pegging Paradise.
1/28/202251 minutes, 6 seconds
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Podcast #286 Completes 2021!

Podcast #286 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 #279 Pegging Celebration Time! Beatrice & Dante do the deed a month after interviewing me! He […] The post Podcast #286 Completes 2021! appeared first on Ruby Ryder - Pegging Paradise.
12/31/202141 minutes, 6 seconds
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Movember Ushers in Podcast #285

Pegging Paradise Podcast #285 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 #285 appeared first on Ruby Ryder - Pegging Paradise.
11/10/202139 minutes, 55 seconds
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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 #284 appeared first on Ruby Ryder - Pegging Paradise.
10/25/202150 minutes, 10 seconds
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Presenting Podcast #283

Pegging Paradise Podcast #283 Presenting Podcast #283 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 #283 appeared first on Ruby Ryder - Pegging Paradise.
10/16/202147 minutes, 48 seconds
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Podcast #282 – Have Issues, Want Advice

Pegging Paradise Podcast #282 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 #282 – Have Issues, Want Advice appeared first on Ruby Ryder - Pegging Paradise.
9/21/20210
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Podcast #281 Pops Up Like Magic!

Pegging Paradise Podcast #281 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 #281 Pops Up Like Magic! appeared first on Ruby Ryder - Pegging Paradise.
9/11/202130 minutes, 5 seconds
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#280 – The Need For Receiver Aftercare

Pegging Paradise Podcast #280 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 #280 – The Need For Receiver Aftercare appeared first on Ruby Ryder - Pegging Paradise.
9/3/202138 minutes, 28 seconds
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Podcast #279 – Challenges for the Old Folks!

Articles/Information Equipment The post Podcast #279 – Challenges for the Old Folks! appeared first on Ruby Ryder - Pegging Paradise.
7/25/202139 minutes, 42 seconds
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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 #278 – On Being a Good Bottom appeared first on Ruby Ryder - Pegging Paradise.
7/23/202133 minutes, 31 seconds
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Oh Boy! Pegging Paradise Podcast #277 is Here!

Pegging Paradise Podcast #276 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 #277 is Here! appeared first on Ruby Ryder - Pegging Paradise.
4/29/202156 minutes, 1 second
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Pegging Paradise #276 Has Arrived!

Pegging Paradise Podcast #276 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 #276 Has Arrived! appeared first on Ruby Ryder - Pegging Paradise.
3/29/20211 hour, 9 minutes, 52 seconds
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Yay! Podcast #275 is Here For You!

Pegging Paradise Podcast #275 Photo credit - PrettyDomme FetLife: https://fetlife.com/users/9700337?sp=1 Only Fans: https://onlyfans.com/prettygfdomme 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 #275 is Here For You! appeared first on Ruby Ryder - Pegging Paradise.
3/12/202151 minutes, 28 seconds
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Great News! It’s Podcast #274!

Pegging Paradise Podcast #274 He shares his crossdressing journey! He and his wife had a go at prostate massage. Fireworks! He wonders about women who peg and don't judge. He asks if there are women who will teach guys pegging She's gone from hesitant to hungry for his ass! Pegging Celebration Time! His story of […] The post Great News! It’s Podcast #274! appeared first on Ruby Ryder - Pegging Paradise.
2/26/202153 minutes, 57 seconds
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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 #273 appeared first on Ruby Ryder - Pegging Paradise.
2/18/202151 minutes, 8 seconds
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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 #272 appeared first on Ruby Ryder - Pegging Paradise.
1/11/20211 hour, 5 minutes, 21 seconds
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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 #271 Part 2 appeared first on Ruby Ryder - Pegging Paradise.
12/6/202038 minutes, 1 second
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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 #271 Part 1 appeared first on Ruby Ryder - Pegging Paradise.
12/6/202044 minutes, 40 seconds
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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 #MeToo Book for Men Links for you - new Ted Talks! Articles/Information Movember Donation […] The post Pegging Paradise Podcast #270 appeared first on Ruby Ryder - Pegging Paradise.
11/26/20201 hour, 6 minutes, 41 seconds
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Pegging Paradise Podcast #269

Pegging Paradise Podcast #269 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 #269 appeared first on Ruby Ryder - Pegging Paradise.
11/5/20201 hour, 1 minute, 41 seconds
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Pegging Paradise Podcast #268

Listen to Pegging Paradise Podcast #268 A reaction to Aussie Man's story (#266) 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 #268 appeared first on Ruby Ryder - Pegging Paradise.
10/26/20200
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Pegging Paradise Podcast #267

Listen to Pegging Paradise Podcast #267! (Long Overdue) Pegging Celebration Time! They are edging into anal play on him and he's excited! Pegging happened! He has questions about making his GF come He wants his wife to have more pleasure during pegging She has fingered his ass - does that mean she's open to pegging? […] The post Pegging Paradise Podcast #267 appeared first on Ruby Ryder - Pegging Paradise.
10/6/20201 hour, 5 minutes, 45 seconds
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Pegging Paradise Podcast #266!

Listen to Pegging Paradise Podcast #266 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 #266! appeared first on Ruby Ryder - Pegging Paradise.
9/17/20201 hour, 8 minutes, 7 seconds
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Podcast #265

Listen to Pegging Paradise Podcast #265 Response to Manly Man's Man letter (podcast #264) 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 #265 appeared first on Ruby Ryder - Pegging Paradise.
8/19/20201 hour, 5 minutes, 49 seconds
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Podcast #264

Listen to Pegging Paradise Podcast #264 New Toy Review! Strap-On-Me Vibrating Double A dominant man finds my erotica, with interesting results! He wants an app controlled cock cage to increase his productivity He wants to be fucked by his wife every day - advice? This man loves big toys and getting fucked more roughly - […] The post Podcast #264 appeared first on Ruby Ryder - Pegging Paradise.
8/7/202059 minutes, 34 seconds
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Podcast #263

Listen to Pegging Paradise Podcast #263 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 #263 appeared first on Ruby Ryder - Pegging Paradise.
7/25/20201 hour, 5 minutes, 56 seconds
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Podcast #262

Listen to Pegging Paradise Podcast #262 Trysexual's continued story! (Spoiler - his birthday was awesome) He's shopping for less expensive XL toys She's new & nervous, he's impatient with her learning curve She tried it. She doesn't like it. He wants only that. They pegged. Now he's saying no, he feels awkward. She wants to […] The post Podcast #262 appeared first on Ruby Ryder - Pegging Paradise.
6/15/20201 hour, 12 minutes, 7 seconds
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Masturbation Month Finale!

Happy Masturbation Month! To celebrate, carouse, and consecrate...I offer audio erotic short stories for you.One every day, all month long, in celebration of self-pleasuring! Clandestine Public Stimulation Enjoy! To the Hilt,Ruby The post Masturbation Month Finale! appeared first on Ruby Ryder - Pegging Paradise.
6/1/20206 minutes, 55 seconds
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Masturbation Month #31

Happy Masturbation Month! To elucidate, expound, and enlighten...I offer audio erotic short stories for you.One every day, all month long, in celebration of self-pleasuring! Six Shots of Patron Enjoy! To the Hilt,Ruby The post Masturbation Month #31 appeared first on Ruby Ryder - Pegging Paradise.
6/1/20204 minutes, 17 seconds
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Masturbation Month #30

Happy Masturbation Month! To make you vacillate, vellicate, and vibrate...I offer audio erotic short stories for you.One every day, all month long, in celebration of self-pleasuring! I Need Help Enjoy! To the Hilt,Ruby The post Masturbation Month #30 appeared first on Ruby Ryder - Pegging Paradise.
6/1/20203 minutes, 56 seconds
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Masturbation Month #29

Happy Masturbation Month! To make you squirm, shiver, and shudder...I offer audio erotic short stories for you.One every day, all month long, in celebration of self-pleasuring! Fake Pearls Enjoy! To the Hilt,Ruby The post Masturbation Month #29 appeared first on Ruby Ryder - Pegging Paradise.
6/1/20207 minutes, 31 seconds
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Masturbation Month #28

Happy Masturbation Month! To perk up, please, and prompt...I offer audio erotic short stories for you.One every day, all month long, in celebration of self-pleasuring! Up Against the Wall Enjoy! To the Hilt,Ruby The post Masturbation Month #28 appeared first on Ruby Ryder - Pegging Paradise.
6/1/20205 minutes, 9 seconds
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Podcast #261

Pegging Paradise Podcast #261 Linkorama Articles/Information Equipment The post Podcast #261 appeared first on Ruby Ryder - Pegging Paradise.
5/31/20201 hour, 5 minutes, 11 seconds