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BDSM pegging
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From the Mailbox

I have spent a fairly good amount of my day today reading a lot of stuff that you have written. I couldn’t read enough!!!! You don’t need me to tell you but I will anyway…you are a great writer. From

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It is good to be the Queen.
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Love These Words

You people who write me are so sweet sometimes, so complimentary and encouraging. Thanks for all of your letters, questions and compliments. I do so appreciate them. A a writer, this one in particular gave me a thrill: “You have

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It is good to be the Queen.
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And The Winner Is…

Thank you all so much for your submissions! I had great fun (literally) reading them all and I salute the juicy creativity you offered up to Pegging Paradise. All entrants will receive a surprise email in thanks for your entry.

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Ruby Ryder
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Harness Question

Dear Ruby, I am a man of 21 and over the year my girlfriend and I have gotten into strap-on play. It started when I want to perform anal on her and her request was only if she could perform

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Courtesy of Wikimedia Commons: Masturbation by Klimt, drawing 1913
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Wanking Month Home Stretch

  I received another entry in my contest! Definitely spiced up my night… Also…a friend graced my mailbox with some very hot pictures of his dildo play and impressive cock. You know who you are….and Thank You, Sir! Those two

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BDSM pegging
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Don’t….Stop…..

  I have already received a couple of entries for my story membership contest…and I have to tell you…   The stories have inspired my own self-pleasuring…and I feel privileged to receive them! What a lovely, sexy window into your

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BDSM pegging
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Relaxation Woes…

Have you ever come across someone who is excited by the idea of strap-on training but can’t seem to relax enough for it to “work?” I’m that guy, I am so excited by it that it’s virtually the only porn

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BDSM pegging
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This is Why I Do What I Do

Ms. Ruby, I have been interested in pegging for a long time now and love your website with all of the great information. I just recently brought the subject up with my wife. Our sex life had become dull and

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Ruby Ryder shares art of woman pegging man restrained to bed in BDSM
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Size Discrepencies…

How does one handle size discrepancies??? NO – I am not talking about Dildos…Or Penises. You people have such dirty, dirty minds…I love you all! I am talking about body sizes. What happens when the pegger and the peggee have

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Ruby Ryder shares diagram of male prostate and surrounding body parts
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Newbie Question – Supposed to Feel Good?

A while ago I asked my girlfriend if she would be okay with pegging, and surprisingly she agreed. After that we stopped by a small sex shop to pick out a cheap beginner’s harness set, with a tiny dildo (we

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