Ruby Ryder – Pegging Paradise – Listen to All Episodes Online

A Complicated Story About Giddi – Short Take 9-23-25 Sep 24, 2025 21:17 What started off as just another Labor Day Sale led me through a complicated story about manufacturers, authenticity, marketing, and more. The wild world of sex toys is difficult to navigate at times. I do my best, and sometimes I might get it wrong. This time, I cannot honestly say whether I got it right or wrong! So here's the complicated story about Giddi.... The sale continues thro

Short Take on a Belated Pegging Celebration Time! Sep 5, 2025 19:11 Photo Credit (Found on Reddit in r/GirlsWearingStrapons u/Lady_Perse): "True Dominatrix, check my personal website ladyperse.com and onlyfans https://onlyfans.com/lady_perse And free onlyfans https://onlyfans.com/lady_perse_free" Short Take 9-5-25 PCT - This short take is the first Pegging Celebration Time I've done in a long time! And it's embarrassingly late, but heartfelt noneth

Short Takes on Power Bottoming, and How to Reignite the Spark May 24, 2025 13:35 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! Modern Love Languages Mojo Upgrade Carnal Calibration Sex Over 30 on Reddit Sex Over

Short Take On Masculine Surrender and Virginity Jan 19, 2025 13:51 Masculine Surrender 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 balance can be refres

Short Take on Feeling Clingy, Depth Injuries, and Condoms Dec 29, 2024 20:26 taking a longer dildo when pegging Feeling Clingy, Depth Injuries, and Condoms! Rectosigmoid Junction Injury - seeking information Condoms on toys? Receiver feeling clingy and needy after pegging Articles and Information Rectosigmoid junction article Removing odors from silicone toys Pegging and aftercare In this short take you will find an attempt at crowdsourc

Short Take – What to Say and Big Toy Questions Dec 15, 2024 21:59 He wonders what to say in the moment for givers who are beginners and asks what I might have wanted to hear! He's puzzling out the details of how to take a bigger toy. The lube must be slippery and they need the right harness so the new toy is over her bits! Articles/Information Different Ways of Opening Up For Pegging - Article Reddit post about Silolis Anal Training Plugs

Short Take on the Initial Insertion Dec 5, 2024 Initial Insertions require good foreplay! 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 you more confidence in tha

Podcast #303 Pops Right Up! Feb 14, 2024 53:52 Pegging Paradise Podcast #303 Just when you wondered if you'd lost me... Another podcast pops right up! Both sides of an amazing pegging story Some new toys after the ANME show! All 3 Webinars are now recorded and available for on-demand viewing Happy Hour Chats with Ruby are now a thing Private consultations can be scheduled here Information/Articles All 3 Webinars

“I Love Seeing You Like This” – Podcast #302 Oct 16, 2023 1:13:48 "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 explorations into crossdressing and chastity. This podcast might be a reassur

Turning the Spotlight on Podcast #301 Aug 18, 2023 57:20 Pegging Paradise Podcast #301 Prince of Pegging Dogs and Cars and Escapes Email lists and marketing Pretty Dildos! Pegging Celebration Time! He finally asks for it and gets it plus more! Vagus Nerve considerations post heart attack He discovers real femdom exists and I talk about consent He is so giving to her that she revisits his love of anal play and he's hopefu

How to Be More Dominant While Pegging Your Partner Jul 10, 2023 11:48 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 full-on BDSM scene with restraints, impact play, and

Here it is! Presenting Podcast #300 Part Two! Jul 9, 2023 51:26 Soft Cock Week is Coming! 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 soft cocks that we

This is it! Presenting Podcast #300 Part One! Jul 9, 2023 1:07:39 Presenting Podcast #300 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 T

Get Down and Get Funky With Podcast #299 Jun 11, 2023 1:08:49 Pegging Paradise Podcast #299 She used to peg him but not anymore. Advice? He wonders if pushing the cock and balls back behind the legs has a point? He wants to find the right formula to increase her enthusiasm and pleasure Pegging Celebration Time! He has Equipment questions after their first 3 times He comments on my article and tells a story Seven words and a grammar

Celebrations and Inquiries – Podcast #298 Apr 7, 2023 46:49 Podcast #298 features talk of the JimSupport Sex Sling Pegging Paradise Podcast #298 Consultations with Ruby are now easy to schedule! PCT! He tells his story, from anal play to pegging PCT! He shares his journey from diet to exploration to pegging! His reflections after one year of pegging He shares his experience with Snug Plugs 1-4 and bicycling! They are exploring mo

Surprise! Podcast #297 Appears! Mar 20, 2023 1:02:45 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 - yay! If you are going to put something in your body, make sure it's safe. That ax

Podcast #296 Interview with Zach Budd Dec 1, 2022 1:08:18 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 stealth sodomy are never okay, and how an enthusiastic yes is the only tru

Podcast #295 It’s Not Hard! Nov 11, 2022 47:43 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 quest for an erection. Let's celebrate soft cocks in al

Podcast #294 Lex Shares About BIG Toys Oct 27, 2022 1:40:41 Mr Hankey's Long John Mr Hankey's Largo 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 a long on

Tickle Your Ears with Podcast #293 Sep 22, 2022 49:04 Podcast #293 - for your listening pleasure! He describes his sexual assault (trigger warning)Short and sweet happy news!He loves feminization and she's concernedHe 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 is a happening thing!Pegging Celebration Time!

An Auditory Delight! Podcast #292 Jul 31, 2022 1:03:39 Listen to Pegging Paradise Podcast #292! Podcast #292 brings you new toys, discussion about dominant and submissive labels, and much more! Ruby discusses Sexual Dominance, Submission and LabelsResponse to ED/age issues from #279Response to wanting to feel pretty #291His story about bisexuality and pegging with his wifeHe wants his wife to get pleasure from peggingNew Strap On Me Cli

Podcast #291 Rolls Into Town Jun 1, 2022 52:37 https://www.reddit.com/r/HiddenStrapon/ 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 aft

Podcast #290 Steps Onto the Stage! Apr 22, 2022 1:00:26 Monster Mitts Washable Vampire Gloves Letter from an appreciative PatronHe struggles with shame due to peggingShe wants to satisfy his desire for masochism during peggingHe loves the anticipation and looking sexy for his partnerHe shares about letting go of the past and asking for anal playPegging Celebration Time!Same couple! He shares their storyPegging Celebration Time!After a slow

Podcast #289 is in the Room! Mar 23, 2022 31:04 Listen to Pegging Paradise Podcast #289 Podcast #289 is in the room and ready to play! No butts in the USAHe discovers about real trust with peggingNew to pegging but not solo play, he has size questions He lets go of the shame and guilt, and talks to his wifeHe has some questions about vibe vs no vibeShe seeks a toy that has no curveHe found Homme Mystere - men's lingerie!Pegging Celeb

Lend an Ear to Podcast #288 Mar 12, 2022 27:44 Ruby Ryder shares long legged woman in red latex stockings and red strap-on with dildo For your listening pleasure - it is indeed time to... Lend an Ear to Podcast #288! She offers more info re: chastity, cuckolding & humiliation questionsHe 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 -

Podcast #287 Greets the New Year! Feb 1, 2022 59:13 NewTumbl.com Podcast #287 Greets the New Year! He sends fan mail!Encouraging pegging with his wife plus CD and ED issuesHe has lube and harness questionsHe has questions about the angle of toy vs rectumShe checks in 5 yrs later on pegging, chastity & cuckoldingHe can relate to the term 'Man Box'Thoughts about the term 'just joking'He craves much, much, more peggingHe wants pegging b

Podcast #112 – The Introduction Jan 28, 2022 51:06 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 reposting it so that the downloader apps will

Podcast #286 Completes 2021! Dec 31, 2021 41:06 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 ToysComment on ED issues from #279Pegging Celebration Time!Beatrice & Dante do the deed a month after interviewing me!He wonders whether to explore pegging...She asked him about b

Movember Ushers in Podcast #285 Nov 10, 2021 39:55 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, what they learned and wh

Into Your Mailbox Falls Podcast #284 Oct 25, 2021 50:10 Reddit/Pegging 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 interesting opportunityHe waxes poetic about their

Presenting Podcast #283 Oct 16, 2021 47:48 reddit/pegging_unkinked Pegging Paradise Podcast #283 Presenting Podcast #283 for your listening pleasure! He wants to be slut shamed; she needs suggestionsHe masturbated with anal play in front of her, and has feels about itTrying to get his wife on board with peggingHe's having trouble with penetration about 3-4 inches inHe's curious about a cleaning bottle and toy sharingPegging C

Podcast #282 – Have Issues, Want Advice Sep 21, 2021 NewTumbl.com Pegging Paradise Podcast #282 Want advice - When he asks for what he wants, she shuts him downShe struggles with self-confidence and the learning curveHe speaks eloquently about opening up and submissionShe understands her husband more after reading my storyHe wonders if pegging encourages cuckolding? Articles/Information Janet Hardy - The Sexually Dominant WomanPeggi

Podcast #281 Pops Up Like Magic! Sep 11, 2021 30:05 NewTumbl.com Pegging Paradise Podcast #281 Ruby shares a few (more) thoughts on Pegging and OrientationRelax, 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 his partner, and finds a measure of peacePegging Celebration Time!He tells th

#280 – The Need For Receiver Aftercare Sep 3, 2021 38:28 NewTumbl.com Pegging Paradise Podcast #280 The need for receiver aftercare and what it can look likeHe'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 MenTony Porter - The Roles Men PlayPodcast #250Brené Brown Listening to ShameSex Positive Therapist Dr. Tom Murray

Podcast #279 – Challenges for the Old Folks! Jul 25, 2021 39:42 newtumbl.com She's puzzled and dismayed by the difficulties of searching for a partner at 65 My thoughts about the challenges older men face with intimacy and age-related ED His thoughts about being a good bottom, and trying to be authentic as a submissive man in the middle east He's arrived, after waiting too long, and puts his feelings into words My podcasts are like a wind

Podcast #278 – On Being a Good Bottom Jul 23, 2021 33:31 Check the perspective - install a bar above the bed...? From r/Pegging_Unkinked 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 well as some generali

Oh Boy! Pegging Paradise Podcast #277 is Here! Apr 29, 2021 56:01 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 peggingThey are inspired by the long story request, and tell theirs!He is courageous, tells his wife about sucking the toy and his bi-curiosityHis wife is not interested, even in

Pegging Paradise #276 Has Arrived! Mar 29, 2021 1:09:52 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 peggingHe's concerned about large girth toys and potential damageHe waxes poetic about his sex life and has a few questions, too!He seeks information about lubesHe seeks books on female dominance and a clit sucking toyNew Discord Chat

Yay! Podcast #275 is Here For You! Mar 12, 2021 51:28 Pegging Paradise Podcast #275 Photo credit - PrettyDommeFetLife: https://fetlife.com/users/9700337?sp=1Only 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 issuesHe wants pegging. She doesn't want to see him as submi

Great News! It’s Podcast #274! Feb 26, 2021 53:57 Pegging Paradise Podcast #274 - Great News! 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 being Mounted in Michigan He has many

A Delightful Listen! Podcast #273 Feb 18, 2021 51:08 I'm on Tiktok! He's seeking harness guidanceHe votes for listeners' whole (long) stories!She'd love some new newbie guidanceHe has equipment questionsHe enjoys dominant pegging with a little pain - it that healthy?He's got some questions about finding his prostateThey love pegging & want to add dominance & submission Articles/Information Ruby on TikTok Strap On Me Vibrating

Pegging Paradise Podcast #272 Jan 11, 2021 1:05:21 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 her to get more pleasure from pegging

Pegging Paradise Podcast #271 Part 2 Dec 6, 2020 38:01 Recap of MovemberMr. Hankey's SalePandemic ReflectionsNew Strap On Me Harnesses!Hot Octopuss Pulse III DuoNexus B-Stroker PlugShe shares thoughts about her love of peggingSearching for a dildo that will insert her squirt!His personal experience and advice about huge toysThey are searching for harnesses for XXL toysAfter hemorrhoid surgery his ass is too sensitive - advice?How to get hard

Pegging Paradise Podcast #271 Part 1 Dec 6, 2020 44:40 Recap of MovemberMr. Hankey's SalePandemic ReflectionsNew Strap On Me Harnesses!Hot Octopuss Pulse III DuoNexus B-Stroker PlugShe shares thoughts about her love of peggingSearching for a dildo that will insert her squirt!His personal experience and advice about huge toysThey are searching for harnesses for XXL toysAfter hemorrhoid surgery his ass is too sensitive - advice?How to get har

Pegging Paradise Podcast #270 Nov 26, 2020 1:06:41 Movember Link to DonateHow I Teach WebinarsThe Man BoxMy story about FrankMy first awareness of the Man BoxAn eloquent share about the Man BoxWhat can Men do?What can Women do?Reading from The Little #MeToo Book for MenLinks for you - new Ted Talks! Articles/Information Movember Donation link for Ruby!Tony Porter - A Call to MenTony Porter - The Roles Men PlayMark Greene - The Littl

Pegging Paradise Podcast #269 Nov 5, 2020 1:01:41 Pegging Paradise Podcast #269 He writes back with more thoughts about cum eatingA Taste Tester shares his journeyHe takes it to the level of pre-cum in a shot glass!His story about coming to terms with his love of penetrationHe is shy to initiate and girlfriend doesn't want to schedule. Help?They have take advantage of the lockdown. He shares!He's starting to crave playing with cocks a

Pegging Paradise Podcast #268 Oct 26, 2020 Ruby Ryder shares woman with corset and strap-on POV from spread legs and penis 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 massagerMy adventures with the We-Vibe VectorPegging Celebration Time!They communicate, work through some stuff and it happens!Pegging Celebration T

Pegging Paradise Podcast #267 Oct 6, 2020 1:05:45 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? She shares Incredibly Eloquently about loving his vuln

Pegging Paradise Podcast #266! Sep 17, 2020 1:08:07 Ruby Ryder shares woman with strap-on pegging man face down on bed Listen to Pegging Paradise Podcast #266 Pegging Celebration Time!He shares his story of their long, and finally successful, pegging journeyHe waxes poetic about men who like pegging not being gayCelt lass tells story of how she found her like-minded partnerPegging Celebration Time!Initiated in December, she gives him th

Podcast #265 Aug 19, 2020 1:05:49 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 prostateShe feels betrayed by his lack of honesty about his butt plugHe's having difficulty transitioning from 1.25" to 1.5" diameter - hints?He needs good positions for

Ruby Ryder – Pegging Paradise

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