Strap-On Before the Woman

Sort of like the cart before the horse.

For the Gentlemen...

Since diving dildo-first into exploring the world of pegging...one thing has really jumped out at me (well, besides the mouthwatering "Outlaw" dildo at Vixen Creations...).

It is this...There are many, many of you men out there who are interested in being pegged, whether you are new to the experience or you have your own equipment in your dresser drawer. You dream of feeling that dildo slide into you, teasing you, filling you up, thrilling you. You want to be used, fucked, lovingly pegged or hammered. You crave it. You want it. You need it. You beg for it! And you frequent any websites where there might be women who are interested in it. Wow.

I guess what I am saying is that you guys who love pegging really love it. I mean really.

Now...I have witnessed how profoundly my guy is affected by pegging. He swoons with pleasure and gets pretty damn loud with passion. In fact he recently described his ass as "wanting and willing"  (that man so knows how to sweet talk me). So, guys, I can understand  your desire to regularly experience that intense degree of sexual bliss.  Once you've had it...you want more. Like your first blow job. You might even obsess about it. I get it. The strength of your desire for pegging is intense. Not to mention that men are pretty single-minded about sex in general.

Which brings me to...the methodology behind your approach of potential pegging partners.

First, I offer you an example of the worst approach I have ever personally experienced.

"your cock would look good in my hole"

I swear to God, just like that. No capitalization, no punctuation, nada. This approach is definitely not recommended if you are interested in finding a woman to peg you anytime in the next century.

From the woman's point of view, here's a hint, guys.  Don't pursue the toy with greater enthusiasm than you pursue the woman. We women who peg, yes, it's nice to know how much you guys enjoy it...but it is also nice to feel like you are interested in us as people first and wearers of dildos second. Get to know us...meet us for coffee or dinner...have some conversations with us. To be pursued as primarily the wearer of a strap-on is quite off-putting; like being used to satisfy your fantasy. (If you truly only want to get pegged and are not interested in the woman doing the pegging, just go find a professional.)

Please remember...There is a woman at the end of that strap-on!

An alternative method of finding a woman who pegs is to find a woman.....and turn her into a pegger. I'm trying to convince a friend to post his story here about how he did exactly that. I think his approach was brilliant...and it was effective.

Here you go - "Vanilla to Pegger - One Man's Story."

Happy Pegging,

Ruby Ryder

11 Responses

  1. Ruby-
    Everything below “your cock would look good in my hole” is wonderfully stated.
    Pegging needs to be (in our bed) the variety, not an obsession. And you are right, she has to be more than just a generic harness driver.
    I like to say; strapon sex, is just sex.
    when done right it is one of the most intimate things a couple can share.
    Thanks for your beautiful site.
    -ryder

  2. Thanks, ryder! I completely agree. You and I are like the strap-on missionaries of the internet! Thanks for your amazing contributions as well…especially your latest writing – excellent.

  3. Dear Ruby,

    Great article as always, you have a great writing style and come across as a very sympathetic (in the Spanish sense: simpatica) lady with a great passion for spreading the…

    …word (couldn’t resist) about the joys of pegging.

    This might not be the best place to ask you, but do you still enjoy PIV sex? How often do you have PIV sex as compared to pegging?

    Also do you ever feel you want to be taken vaginally after giving your man a good pegging?

    Cheers,
    Mark

    1. I did a podcast recently where my listeners asked me all kinds of questions and I believe this one was in there. Absolutely I enjoy PIV sex a lot. And PIV after pegging is lovely, yes, but not often the order I do things in. I like to make a man come with pegging and if necessary, penile stimulation. After that, he’s rarely ready for the immediate penetration I crave, so a couple of fingers on my G-spot can be very nice…

  4. Thanks for your reply, Ruby.

    If I could make a suggestion to men seeking pegging.

    I have often heard stories of men who asked a woman for anal sex only to be met with a response like “only if you’re willing to try it first to see how it feels”.

    If that happens, you’re in – or she is! 😉

    1. I have suggested this many times in the reddit/sex group – only to be flamed by guys who can’t see the logic and are homophobic around anal play. I totally agree with you!

  5. I am in big trouble in a good way, I found someone who is experienced in pegging, who gets turned on by the experience of fucking a man. She is of asian descent, and casually brought it up during a massage which includes happy endings. I CAN’T STOP THINKING ABOUT THE TWO EXPERIENCES I’VE HAD IN THE TWO LAST MONTH. I’m also anxiously waiting waiting on my third encounter, I’m afraid that it will never happen, because she could end up moving back to her home country. Well the joy of my life happened for the 1st time in the month of December 2018. I’ve waited my whole life to be pegged properly, my whole body shook while she just kept repeating “oh my god” the session lasted an hour of pegging and one hour of a full body massage.
    During the happy ending session, while she was stroking me, I was rubbing her ass building to an explosion, she casually asked if I liked to fuck a woman in the ass, I replied yes and she said that she liked to fuck a man the same way….and the rest is history !!!

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