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Ruby Ryder – Pegging Paradise

Ruby Ryderpeggingparadise.com
Your guide for pegging, anal sex, and bdsm
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Episodes

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

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 entire month of September, should you wish to give the Tomo a try, after hearing my story! Gadget Revie...

Sep 24, 202521 min

Short Take on a Belated Pegging Celebration Time!

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 enjoy her story. I feel like this contributor embodies the best of intentions and consideration in h...

Sep 05, 202519 min

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! Modern Love Languages Mojo Upgrade Carnal Calibration Sex Over 30 on Reddit Sex Over 50 on Reddit And just in case you missed it - My article about CBD Lubes and Suppositories! Masturbation Month 2025 has been ...

May 24, 202514 min

Short Take On Masculine Surrender and Virginity

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 and healing. Not having to be in control can be a relief, startling in contrast to the daily expect...

Jan 19, 202514 min

Short Take on Feeling Clingy, Depth Injuries, and Condoms

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 play injury at the rectosigmoid junction. He also had a horrible experience with an MD who couldn't ...

Dec 29, 202420 min

Short Take – What to Say and Big Toy Questions

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 Rectosigmoid Junction - Article Equipment Fukena Sliquid Silk X-Lube CBD Butt Stuff CBD Palm Grease Extra Gre...

Dec 15, 202422 min

Short Take on the Initial Insertion

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-important moment of sliding it home! WTF are Short Takes? This is the first of what I am calling my Shor...

Dec 05, 2024

Podcast #303 Pops Right Up!

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 Strap On Me Unique Harness dual penetration one size waist 25 - 35 Strap On Me Tapping Wave Dildo 6"...

Feb 14, 202454 min

“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 explorations into crossdressing and chastity. This podcast might be a reassurance to pegging givers who are concerned when their receivers express a desire to crossdress. Hearing per...

Oct 16, 20231 hr 14 min

Turning the Spotlight on Podcast #301

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 for him is so many wonderful ways He seeks a solution to a complicated toy issue Information/Articles ...

Aug 18, 202357 min

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 full-on BDSM scene with restraints, impact play , and humiliation. A desire I see expressed often by receivers in pegging groups on Reddit , and in emails sent ...

Jul 10, 202312 min

Here it is! Presenting Podcast #300 Part Two!

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 discuss. Even how the word cock seems to be more favored by one racial demographic - with no studies to ...

Jul 09, 202351 min

This is it! Presenting Podcast #300 Part One!

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 Podcast #200 Part One And Podcast #200 Part Two Podcast #200 Part Three Stan Tatkin - Wired For Love Jessi...

Jul 09, 20231 hr 8 min

Get Down and Get Funky With Podcast #299

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 question Sub seeks prostate orgasm and wants more pleasure for his mistress He's post-op prostate cance...

Jun 11, 20231 hr 9 min

Celebrations and Inquiries – Podcast #298

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 and terrified all at once! Articles/Information Zoom Consultations with Ruby Review of JimSupport Sex...

Apr 07, 202347 min

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 - yay! If you are going to put something in your body, make sure it's safe. That axiom applies to toys as well as lube! For those of you interested in different techniques to help open up to p...

Mar 20, 20231 hr 3 min

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 stealth sodomy are never okay, and how an enthusiastic yes is the only true consent. Last but far from least, Zach shares the tip of the iceberg on the subject of anal receptive play for...

Dec 01, 20221 hr 8 min

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 quest for an erection. Let's celebrate soft cocks in all their glory! It's not hard, head over to the website and check out all the offerings from so many different ...

Nov 11, 202248 min

Podcast #294 Lex Shares About BIG Toys

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 intended)! Right as I was putting this podcast together, I received a promotional email from Mr. Hank...

Oct 27, 20221 hr 41 min

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 is a happening thing! Pegging Celebration Time! After 3 years, it finally happened Pegging Celebration Time! Peggers from Belgium - He tells their stor...

Sep 22, 202249 min

An Auditory Delight! Podcast #292

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 Vibrating Double! Listener shares many thoughts revolving around pegging She wasn't fully on board w...

Jul 31, 20221 hr 4 minSeason 1Ep. 292

Podcast #291 Rolls Into Town

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? Pegging brings up his lack of vulnerability in his relationship Then, he sends a vote for men feel...

Jun 01, 202253 min

Podcast #290 Steps Onto the Stage!

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 start, their pegging play takes off! Their partner has femininity concerns around wearing a strap-on He ...

Apr 22, 20221 hr

Podcast #289 is in the Room!

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 Celebration Time! After 9 years, he asks and she says yes! Articles/Information Podcast #112 - Introduction fo...

Mar 23, 202231 min

Lend an Ear to Podcast #288

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 gussying up the harness that fits! Ruby was kicked off IG, and made another account (eye roll) Begin...

Mar 12, 202228 min

Podcast #287 Greets the New Year!

NewTumbl.com 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' Thoughts about the term 'just joking' He craves much, much, more pegging He wants pegging but doesn't want to push his wife Articles/Information Crossdressing Podcast #131 CD Podcast #182 Part O...

Feb 01, 202259 min

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 reposting it so that the downloader apps will include it once again. (If you are looking for the podcast #253 for prospective receivers, click here .) I recorded t...

Jan 28, 202251 min

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 wonders whether to explore pegging... She asked him about butt stuff! He is thrilled. A small toy left him sore - advice? Pegging Celebration Time! They rediscovered...

Dec 31, 202141 min

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, what they learned and what advice they have for other men who are struggling. These were all taken from the Movember website. This is the mont...

Nov 10, 202140 min

Into Your Mailbox Falls Podcast #284

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 opportunity He waxes poetic about their new love of 'leather strappage' He shares about age, virility, touch, and aftercare His eloquent story about a sess...

Oct 25, 202150 min
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