Ruby Ryder's Pegging Paradise

[email protected] (Ruby Ryder)

Pegging is a sexual practice in which a woman penetrates a man's anus with a strap-on dildo.

  • 21 minutes 17 seconds
    A Complicated Story About Giddi – Short Take 9-23-25
    The Giddi Tomo, and the complicated story!

    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!

    The post A Complicated Story About Giddi – Short Take 9-23-25 appeared first on Ruby Ryder - Pegging Paradise.

    24 September 2025, 3:16 am
  • 19 minutes 11 seconds
    Short Take on a Belated Pegging Celebration Time!
    User "Lady_Perse" on Reddit

    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 her efforts towards a happy relationship with her partner. We could probably learn a few things!

    Info and Articles

    Upcoming Office Hours

    • Saturday September 20 @ 10AM PDT
    • Tuesday September 23 @ 5PM PDT

    Join the conversations!
    https://us02web.zoom.us/j/8053306466
    Passcode: pegging

    The post Short Take on a Belated Pegging Celebration Time! appeared first on Ruby Ryder - Pegging Paradise.

    5 September 2025, 10:20 pm
  • 13 minutes 35 seconds
    Short Takes on Power Bottoming, and How to Reignite the Spark
    short take on power bottoming and reigniting 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!

    And just in case you missed it - My article about CBD Lubes and Suppositories!

    Masturbation Month 2025 has been largely ignored by me - My apologies! Some of you may have been waiting for new chapters of the on-going story, Seven Days as a Kitchen Maid. If you have not read it, there are currently 29 short chapters. I started the story in 2022 and only seem to be inspired to add to it during May...until this year. I promise that it's on my list to finish! Never has it taken so long to tell about 7 days, right? Erotic anticipation at it's best (or worst - lol). At this point, Frank is quite tempted to do some power bottoming, but he won't. He's being a good boy for Cynthia. Only two more days left! But so very many adventures...

    The post Short Takes on Power Bottoming, and How to Reignite the Spark appeared first on Ruby Ryder - Pegging Paradise.

    24 May 2025, 1:00 pm
  • 13 minutes 51 seconds
    Short Take On Masculine Surrender and Virginity
    Masculine SurrenderMasculine 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 expectations of society.

    And the stuff about 'virginity'. Whew. Perhaps it was an innocent question, but the word itself represents so much bad stuff, and not any good that I can see. Educate yourself. Carry the good forward and discard the bad. The concept of virginity isn't doing anyone any favors.

    You'll hear this in the recording, but I will be leaving Instagram and Threads today, the 19th. There are a lot of reasons, most of which many of you will also be familiar with. I will not participate in a social media platform that simply doesn't care about hate speech and misinformation. Since most of my connecting with you lovely folx happens on Fetlife.com and Reddit, I can make this move and not have it affect me negatively. I'm really liking BlueSky. Give it a try - link below.

    Info and Articles

    The post Short Take On Masculine Surrender and Virginity appeared first on Ruby Ryder - Pegging Paradise.

    19 January 2025, 7:59 am
  • 20 minutes 26 seconds
    Short Take on Feeling Clingy, Depth Injuries, and Condoms
    taking a longer dildo when peggingtaking 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

    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 get beyond his own discomfort to give good care.

    Next, she wonders why all people don't use condoms on toy?

    Finally, he's new at pegging, and was very surprised at the emotional fallout afterwards. Namely, feeling clingy and needy for a couple of days afterwards. This question was on Reddit and one commenter responded so well I felt like you all needed to hear it. That link will take you to the original post.

    Sale of all 3 of my Webinars good through the end of the year! You need this is your sex education library!

    Here's to much more pegging in 2025. I think we can all, or almost all, toast to that! Happy Holidays to you all and may you enjoy the loveliest celebration(s) ever.

    The post Short Take on Feeling Clingy, Depth Injuries, and Condoms appeared first on Ruby Ryder - Pegging Paradise.

    29 December 2024, 8:01 am
  • 21 minutes 59 seconds
    Short Take – What to Say and Big Toy Questions
    what to say with bigger toys
    • 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

    Equipment

    Webinar Sale is ON - Limited Time Offer

    All 3 of my Webinars - the Premium Pegging Package - are now on sale until the end of the year, discounted from $99 to $75! This enables you to have a six hour complete educational pegging library on hand for new partners, additional partners, or for your own review. The best part about the recorded webinars is the on-demand flexibility that allows you to view them on your own time frame as opposed to when I have a free webinar scheduled.

    The post Short Take – What to Say and Big Toy Questions appeared first on Ruby Ryder - Pegging Paradise.

    15 December 2024, 8:01 am
  • Short Take on the Initial Insertion
    Initial Insertions require good foreplay!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 that all-important moment of sliding it home!

    WTF are Short Takes?

    This is the first of what I am calling my Short Takes. Shorter audio clips and more often is the goal. Hope you enjoy. Might be easier to listen to shorter podcasts as well. Having a tough time at the family gathering? Take 10 minutes out and listen to me talk about dildos and asses! I plan to drop these on no specific schedule, but will strive to satisfy all you listeners who have been so deprived on my podcasts.

    Upcoming Sale

    Advance notice of year end sale on all 3 of my Webinars. The Premium Pegging Package will go on sale December 15th through the end of the year, discounted from $99 to $75. This will enable you to have a complete educational pegging library on hand for new partners, additional partners, or your own review.The best part about the recorded webinars is the on-demand flexibility that allows you to view them on your own time frame as opposed to when I have a webinar scheduled.

    Happy Pegging and No Shame!

    The post Short Take on the Initial Insertion appeared first on Ruby Ryder - Pegging Paradise.

    5 December 2024, 8:00 pm
  • 53 minutes 52 seconds
    Podcast #303 Pops Right Up!

    Pegging Paradise Podcast #303

    Anal training cone pops right up

    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

    Equipment

    I hope you enjoy this podcast. Speaking of something that pops right up, there are two inflatable toys for you to check out this time! One from my last blog post, The Strap On Me Inflatable, and a new one from B-Vibe, the Expand, which luxuriously inflates with the touch of a remote.

    Also - the story from the couple is heartwarming and a pure pleasure to listen to. I do spend a fair amount of time solving problems and giving relationship advice here at Pegging Paradise. What a treat to get a purely good news story! In fact, I felt compelled to play the music for them.

    Happy Pegging and No Shame!

    The post Podcast #303 Pops Right Up! appeared first on Ruby Ryder - Pegging Paradise.

    14 February 2024, 2:00 pm
  • 1 hour 13 minutes
    “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 personal stories can be heartening and enlightening. Enjoy!

    Information/Articles

    Equipment

    Movember officially begins in November. I will indeed be participating once again with the same goal of $1000. I'm starting early (October 15th) because my goal this year is not a specific workout goal. Instead, it's a weight loss goal! This is why I am starting early. I plan to lose 15 pounds by the end of November and reverse the effects of the pandemic on my fitness. I'm strong from all my workouts but would love to be able to fit back into some of my clothes and move through the world more easily. Extra weight impacts me more intensely as I get older! And I need to stay fit so I can keep enthusiastically having my way with my partners...!

    Please donate to the Movember fundraiser if you are able. They are doing such amazing work!

    The post “I Love Seeing You Like This” – Podcast #302 appeared first on Ruby Ryder - Pegging Paradise.

    16 October 2023, 1:00 am
  • 57 minutes 20 seconds
    Turning the Spotlight on Podcast #301
    Podcast #301 is a celebration of pegging

    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

    Equipment

    I hope you enjoy podcast #301! I included a link to an instagram video from Joe Kort that relates to my new article posted on 7/2, "Men Like to Feel Beautiful and Wanted, Too". There's a lot to this line of thinking. I think the reasons that women are not as good at expressing their desire for men are complicated, but that doesn't mean that the desire to receive compliments and feel wanted is not there. Please take some time and consider this.

    BIG SALE: Mr Hankey's is having a sale! From now until August 31st, the code SUMMER20 will get you 20% off storewide! Shop.

    Happy Pegging and No Shame!

    The post Turning the Spotlight on Podcast #301 appeared first on Ruby Ryder - Pegging Paradise.

    18 August 2023, 7:00 pm
  • 11 minutes 48 seconds
    How to Be More Dominant While Pegging Your Partner
    Being More Dominant in Pegging

    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 to me is for the giver to be more dominant.

    "How can I get my partner to be more dominant while fucking me?"

    "Sometimes I really wish she would just grab me and fuck me and act a little more dominant."

    "I've asked my partner to be more dominant, but she said she doesn't know how."

    This is a common desire in the world of pegging. So how can couples best navigate this added aspect to their pegging play? I recorded my thoughts on this subject for you all. The answer is more involved than you would think. Good communication is essential. Knowing what you like and dislike is also important for both givers and receivers.

    Remember, the willingness to explore is commendable and a true gift to your partner and your relationship! You don't know whether you will like it if you have never tried it, right?

    Happy Pegging!

    The post How to Be More Dominant While Pegging Your Partner appeared first on Ruby Ryder - Pegging Paradise.

    10 July 2023, 6:03 pm
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