Ruby Ryder

Ruby Ryder – Pegging Paradise

Health EN ↓ 50 episodes

Your guide for pegging, anal sex, and bdsm

Author

Ruby Ryder

Category

Health

Podcast website

peggingparadise.com

Latest episode

Sep 24, 2025

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Episodes

A Complicated Story About Giddi – Short Take 9-23-25 24.09.2025

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 through the ent...

Short Take on a Belated Pegging Celebration Time! 05.09.2025

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 nonetheless. Hope you...

Short Takes on Power Bottoming, and How to Reignite the Spark 24.05.2025

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 50 on Reddit And just in...

Short Take On Masculine Surrender and Virginity 19.01.2025

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 refreshing, wondrous...

Short Take on Feeling Clingy, Depth Injuries, and Condoms 29.12.2024

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 crowdsourcing for a gentleman who had a depth...

Short Take – What to Say and Big Toy Questions 15.12.2024

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 All About the Rectosigm...

Short Take on the Initial Insertion 05.12.2024

Initial Insertions require good foreplay! Initial Insertion Short Take Jessica's question is common for new Givers. She's concerned about g etting 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 that all-impo...

Podcast #303 Pops Right Up! 14.02.2024

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 Recorded Happy Hours Equipment...

“I Love Seeing You Like This” – Podcast #302 16.10.2023

"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 reassurance...

Turning the Spotlight on Podcast #301 18.08.2023

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 hopeful Podcast #112 is a lighthouse fo...

How to Be More Dominant While Pegging Your Partner 10.07.2023

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 humili...

Here it is! Presenting Podcast #300 Part Two! 09.07.2023

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 disc...

This is it! Presenting Podcast #300 Part One! 09.07.2023

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 One Pegging Gangbang Interview #146 Part Two Podcas...

Get Down and Get Funky With Podcast #299 11.06.2023

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 lesson Shout out and a que...

Celebrations and Inquiries – Podcast #298 07.04.2023

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 more and more. He’s excited a...

Surprise! Podcast #297 Appears! 20.03.2023

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 axiom appli...

Podcast #296 Interview with Zach Budd 01.12.2022

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 true consent. L...

Podcast #295 It’s Not Hard! 11.11.2022

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 all their gl...

Podcast #294 Lex Shares About BIG Toys 27.10.2022

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 one (another pun i...

Tickle Your Ears with Podcast #293 22.09.2022

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 is a happening thing! Pegging Celebration Time! Aft...

An Auditory Delight! Podcast #292 31.07.2022

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 Labels Response to ED/age issues from #279 Response to wanting to feel pretty #291 His story about bisexuality and pegging with his wife He wants his wife to get pleasure from pegging New Strap On Me Clit Sucking...

Podcast #291 Rolls Into Town 01.06.2022

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 after a prostatectomy...

Podcast #290 Steps Onto the Stage! 22.04.2022

Monster Mitts Washable Vampire Gloves 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 Celebration Time! After a slow star...

Podcast #289 is in the Room! 23.03.2022

Listen to Pegging Paradise Podcast #289 Podcast #289 is in the room and ready to play! 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 that has no curve He found Homme Mystere - men's lingerie! Pegging Celebratio...

Lend an Ear to Podcast #288 12.03.2022

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 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 suggests...

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