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Ruby Ryder – Pegging Paradise

Your guide for pegging, anal sex, and bdsm

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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…

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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…

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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…

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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…

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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…

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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…

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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…

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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…

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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 explorations into crossdressing and chastity. This podcast might be a reassurance…

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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…

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