Apr 10 2011

Who, What, Why, Where and When!

Ruby pic for About page


My name is Ruby Ryder. Not my real name, but my nom de plume.


Pegging. Strap-on sex. The woman straps it on. The man takes it.


For decades, I felt shame about my sexual desires. I suppressed them, hid them away and labeled them bad, different, and strange. Despite my attempts to suppress my desires and fantasies, they persisted. After my 50th birthday, I realized that suppression had no place in the life I wished to live. I wanted to celebrate my desires and fulfill them, not shame myself for having them. That's when I started this blog.

I discovered that there were a lot of other people who fantasized about and practiced pegging just like me! Together, we are letting go of the shame, embracing our desires and telling our stories....changing the world, one ass at a time!


Here at Pegging Paradise you can find out all about pegging. I mix a little kink in with it, because that's how I am. If kink isn't your thing, Pegging101.com has all the informational articles without the kink!

The other where question - I reside in the Ventura, California area and love watching the surfers change out of their wet suits when I go to the beach.


Right now, of course! Don't wait decades, like I did. If you have any interest in exploring pegging, do it now!


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Who, What, Why, Where and When!, 9.6 out of 10 based on 8 ratings


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  1. I’ve always wondered about something…how many men can actually get an erection when they’re being pegged? I’m one that can’t and I’m sure I’m not alone. Have you ever done a survey?

    1. I can’t get fully erect either, just enough to stroke myself off. But when she gets the right angle and hits the prostate the orgasm is intense.

      1. That’s the word I hear most often in connection with prostate orgasms – ‘intense’. 🙂

    2. I have not done a survey, and I’m quite sure no one else has, either. But if I had to guess, I’d say it’s about 60% can and 40% can’t. Many of the men who can’t are still able to come with penile stimulation, even while soft.

  2. Too bad you don’t do webinars when doing events since being in Long Beach, we over here in south Florida could attend. You’re very knowledgeable and helpful about pegging.

    1. Definitely planning on doing more webinars soon!
      I will schedule one after the holidays, in January.
      Is there a time/day that works better for you?

  3. just need to know how to meet girls interested to pegging with me

    1. Here is a list of articles that I wrote that all address different aspects of wanting to find a woman to peg you. Good luck to you!

  4. I have just started listening to your podcasts, and I absolutely LOVE them. thank you so much for what you do.

    1. So glad you are enjoying the podcasts! Sweet of you to the time and let me know. 🙂

  5. Note – I censored the names of the toys, as I cannot recommend these. They are not body-safe, non-toxic toys. If anyone reading is interested in what the brands/toys are, please contact the commenter on FetLife.com (name at bottom of this comment).

    Hi Ruby,

    I also just started listening to your podcasts. I have never downloaded the app until a hour ago. Podcast 162 has some interesting letters. One about 9 by 7 inch dildo. Will he like to go back to smaller ones, My opinion Is no, but I might be wrong, me being a size queen and and a very experienced anal player, I never wanted a smaller one , always bigger and bigger. The feeling I get from upsizing is unimaginable. I think it’s something to do with my prostate gland , I think it likes a lot of pressure on it . I have a very large collection of dildos. I threw all of my dildos away that were smaller than 3″ wide. A 3″ wide dildo seems to be the magic number for me. I probably still have 25 really big dildos still that are between 3″ wide and 4″ wide . I have to really work up to take a 4″ , after that , I feel very very loose , like I have been fisted, my sphincter muscles are so loose that I refrain from doing anal for at least a week for my rectum to shrink back up. The best all around size dildo that I use and don’t have any problem with leakage is a 3″ wide. I have found that it puts the perfect pressure on my prostate to give me a very intense ejaculation. As far as length , I have found that I am very comfortable taking 10″ in length very easily and fast , anything else I have to go very slow .

    I would like to recommend a couple of dildos for all you males out there that want to get really aroused.
    ******** 12″ black is a very stimulating dildo, it has a small tapered head 2.75″ for easier entry and the shaft is a stout 3″ thick with large veins that you can feel rubbing on your prostate gland. A must for any male that wants to go bigger than the Tantus Hoss , which has a 2.75″ head.
    Another very nice choice is a dildo called ********* , made by *****, this dildo has a special material called ********. Now this dildo is very long , at 16″ in length , 13.50″ insertable, you have to be really greedy to take all of this one. The head is 3″ wide and the shaft is a little smaller, like 2.80″ wide but veiny also . The suction cups work excellent on both dildos so when your wife is not home you can stick them to the shower wall and give yourself a great workout. I myself like to stick ********* to the floor by the tub and go down on it and use my arms on the tub to help hold myself up so my legs don’t wear out so quick. I like to let the 3″ head pop in and out popping my sphincter and also deep stroking it fast so I can feel the veins. I get off really good like that.

    Hopefully this info will be good for someone that is worried about leakage or damage. 3 inches will fill any man up, 4 ” will too but like I said it take you anus a while to shrink back up. I also noticed that I can have a more intense orgasm with the 3 inch cocks , when I use the 4″ I seem to want to hurry up and take it in for a few minutes and then I’ve had enough, a very intense stretching that leaves me wide open and kinda sore.

    I have been into anal for years , in a heterosexual man with a very kinky side. Never been with a man nor do I desire to. I might not mind having a threesome and be blindfolded and let some man fuck me up the ass as long as he it very big and long, if I’m going to do it I want to make sure I am fucked really good and hard.
    I have stuffed all kinds objects into my ass just like a lot of other people have, from shampoo bottles to very large cucumbers, the cucumbers come from my garden I grow every spring with no insecticide of course, I love to watch how quick and around they get before I fuck them. I love the prickly nubs on the big thick cucumbers rubbing on my prostate gland, very stimulating, I have grown some 3 1/2″ wide and 4″ wide ones and the way they are tapered makes insertions a breeze as long as you loosen up first

    Thanks Ruby for your podcasts, I love listening to your erotic voice.😘

    Giantcockfuck @

    1. Thanks for your comment – there are not so many size kings out there so I appreciate the input. I have been asked before how long it takes for the rectum to shrink back to a normal size and if there is any leakage before that happens. I imagine it is different for different men, but it’s great to hear your experience to add to the knowledge base.

      I can’t however, in good conscience, recommend most of the toys you speak of, because they are not non-toxic and body-safe. Those were censored – and readers can contact you on FetLife is they are curious!

  6. Hi Ruby,

    That’s fine about censoring my big dildos, you know if you by the magnum xl condoms they will slide over a 3″ wide or a 3 1/2″ wide dildo without tearing. I have done it plenty of times. I also would like to say that if I don’t play with a dildo for a while, I can’t take a 3″ wide anymore, my hole shrinks up very small, like a regular person so if anyone is worried about that , don’t, it will get small again.
    I have to use some of my glass dildos to loosen my hole back up to take a 3″ wide one, another thing that helps is getting one of those enema shower systems. I always do about 3 or 4 nice warm enemas before any anal play.
    Warm enemas will also loosen and relax your sphincter muscles so you can accept a bigger dildo.
    After the enemas, I like to just sit on the edge of the tub and let the warm water flush my insides and all around my lips ,then I like to use KY Warming Gel and finger myself while my ass is hanging over the tub still, then I will have the big dildo stuck to the floor and wipe KY on it and just start sliding down on it , omg it feels so good to have a 3″ wide dildo stroking my insides, I don’t think that anything feels better in this world that that.

    If anyone has a question or would like to chat about big dildos and how to take them or would like to see me take them , please don’t hesitate to message me. Go to
    Open a free account, then type in giantcockfuck and send me a message.
    I would be happy to help you with any questions or if you would like the see me insert some very lovely big dildos.

    Thanks Ruby for your awesome site!!!

  7. Hey ruby a just listened to your hard times at the hotel story and a must say a thought it was excellent. 🙂 one of the best story’s I have had the pleasure of reading /listing to.
    I also wanted to ask you about the part where you say about going on dating sites as anonymous where you thought what the hell and let your kinks out into the world. Well here is my question. I was wanting to know was it just a normal dating site or was it like a sex dating site? As I am currently looking to try out a few things as well as pegging, but don’t know how to bring them up and where to find the people that I can speak to about it. lol

    1. Thanks for the comment. I read it and responded on podcast #174, which will post just after midnight PST. Here’s the link:

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