Ruby Ryder – Pegging Paradise artwork

Sexuality · Ruby Ryder

Ruby Ryder – Pegging Paradise

by Ruby Ryder

Your guide for pegging, anal sex, and bdsm

Latest episodes

Showing 20 · updated from the feed

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 d

Sep 24 2025
21 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_pe

Sep 5 2025
19 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 c

May 24 2025
13 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 'vi

Jan 19 2025
13 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 c

Dec 29 2024
20 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. T

Dec 15 2024
21 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 getting the toy in so the fun

Dec 5 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

Feb 14 2024
53 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

Oct 16 2023
1 h 13 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

Aug 18 2023
57 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 lo

Jul 10 2023
11 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 expl

Jul 9 2023
51 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 C

Jul 9 2023
1 h 07 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

Jun 11 2023
1 h 08 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 an

Apr 7 2023
46 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

Mar 20 2023
1 h 02 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 jo

Dec 1 2022
1 h 08 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

Nov 11 2022
47 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 des

Oct 27 2022
1 h 40 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 concernedHe intro

Sep 22 2022
49 min

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