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.

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 I get 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 via email.

“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. Here is a story from a friend of mine who did just that: “Vanilla to Pegger – One Man’s Story.”


Happy Pegging,

Ruby Ryder

Pegging…this thing we love and indulge in with such passion and excitement…requires equipment. Indeed, much has been discussed here at Pegging Paradise about the necessary equipment; lube, harnesses and dildos. Let’s back up a step, though. Let’s talk about the step between “Approaching Her About Pegging”  and the act of pegging itself.


She needs to actually strap on a cock

This is not as easy for a woman as you may think. I am going to address this article to you men who want more than anything for your woman to fuck you with a strap-on. Let’s say you have already broached the subject – she’s interested and is considering it….

  • Assuming she understands that the male prostate can provide intense pleasure and she really wants to give her partner pleasure
  • Assuming that she has gotten past the misconception or fear that her partner is gay
  • Assuming that she is open enough to not be freaked out by sex toys in general

Even assuming all the above, actually strapping on a cock may be a huge step for a woman. If you sense some reticence, consider the following…

She is being asked to do something that messes with strict social gender roles. Though one can say it’s just a toy and it doesn’t mean anything other than that you like to use toys…that’s not the reality of it in that moment when the buckles are fastened and she has…a cock. Having a cock, penetrating and thrusting are quite male-associated things. The whole idea that she could take on the active, penetrative role might take a while for her to adjust to.

Some women have fears that they will look ridiculous. Partly because they have never had a cock hanging between their legs and it looks quite strange from their perspective. What most women do not realize is that if their guy is interested in strap-on sex, actually seeing her put on a harness and dildo is so hot they can barely stand it! (And she thought she would look ridiculous…)

There are women who cannot reconcile wearing a cock with their femininity…they want to be feminine and see strapping on a cock as acting like a man. Though it is far from that cut and dried, there is no denying that the role of strapping on a cock and fucking her man requires a woman to be active instead of passive, giving as opposed to receiving, penetrating instead of penetrated.

Indeed, there are a fair amount of emotional factors that can interfere with…strapping on the cock.

So take it slow. Let her hold the dildo in her hand without the harness and fuck you with it first for a few times so she can see how intensely it turns your crank. The first time you use the harness…try to have it fairly well adjusted from a previous try-on so she can just step into it and you don’t have to struggle with getting it just right. Otherwise all the straps can be a lot to figure out. Once on – tell her how unbelievably beautiful and hot she looks…because you know she will.


Remember, she’s never used a cock before

Another concern women have when strapping one on for the first time is that they have no idea how to use it. They are completely unfamiliar with the body motions required to fuck their guy.The lovely hip roll and thrusting instinct that men have is a learned skill for a woman. At first it feels quite awkward and it is common to feel a little ridiculous. For the first time she does you…suggest that she lie on her back and you can ride her. That eliminates the skill factor on her end – and gives her a great view! Plus access to your cock, which in pegging play is always a good thing. (Do make sure you tell her that it is common and normal for men to lose their erections or for them to come and go and it still feels incredible.) Tell her this so she won’t worry whether you are having a good time or not. And keep telling her how good it feels while you are riding her. Make sure she has no doubt that you love it.

Above all…have fun! Don’t get too serious about it all. Laugh and play and talk and experiment together…that’s the stuff good sexual relationships are made of.

Ruby Ryder