I Need a Woman to Peg Me!




Are you single?

Do you love pegging or are you looking to explore it?

Are you wondering how to find a woman that will happily, or even better...eagerly, indulge your particular yearning?


I get the same question over and over again:

Where can I find a woman to peg me?

Well...first let me dispel some myths.

There are no pegging "clubs" where happy ladies run around ready to sink their sizable strap-ons into any willing male who is interested.

There is no internet website where ladies who love pegging are just waiting to hook up with men for a NSA pegging encounter. Don't waste your money - there are very very few women on those sites, despite what they'd like you to believe. Plus, many of the women are fake profiles, pros or online fantasy-only women who you will never meet.



Why is it so hard to find a woman who likes pegging?

It's not. What's hard is to find a woman who enjoys pegging and is ready to peg a stranger. Just like it is hard to find a woman who enjoys sex and is ready to fuck a stranger.

Just because you both like pegging, that doesn't mean she is ready to peg you. Just like because you both like sex doesn't mean she's ready to fuck you.


Pegging is Not Bowling

This is not bowling, guys.

Hey! You like bowling! Me too. How about we go bowling sometime?

No. This is sex. Sex with all of its naked, intimate, vulnerable penetrations and entwining.

I'm happy that you guys have managed to find your way safely through the minefield of misconceptions, fears and social taboos that surround pegging and have come out the other side very interested in having a woman slide her strap-on deep inside you. Kudos to you. Well done.

Now. Approach finding a woman to peg you the exact same way you would approach finding a relationship. Be as charming, clever, polite, fun, interesting and considerate as you know how to be. Whether in person or online.


How to Approach a Woman

If you are on a Vanilla dating site, send a letter of introduction with correct spelling and good grammar. Tell her a little about yourself. Talk about something in her profile that you liked and why. Tell her you are interested and would like to hear from her. This, of course, is after you have put up a decent profile, and please choose a decent user name - don't do the FckMyAss thing. You don't want to lead with that. Use your best judgment to discern if she is sexually open-minded. Date her, get to know her. After you have taken each other for a test drive sexually, if all feels good then talk with her about the pegging. Using finesse. Do not present it like you have leprosy. Present it like a very cool thing that she gets to do with you because you love it. This might help.

If you are on a website that allows you to see if she is interested in pegging and you know she is, DO NOT MENTION IT IN YOUR MESSAGE. I will tell you how that comes across to us women who love pegging. Like you are pursuing us for our strap-on and you could care less about the woman underneath. Like you want us to satisfy your desire to be pegged and that is what is at the forefront of your intentions. We are not a fetish delivery system. And we will drop you like a hot potato if you treat us like one. In fact if things go swimmingly online, meet a couple of times and if she doesn't bring it up DO NOT MENTION PEGGING. I had one guy, after a fine dinner, tell me he had his toys out in the car...did I want to see them? Bringing sex toys for a show and tell on the first date? Yuck! Zero class.


Women Want to Be Treated Like People

Women don't just peg asses, they peg men. We do not see just your body part, no matter how lovely your ass might be. We see a person connected to the ass and hope he's a nice guy, someone we want to do more than fuck. Just because we love pegging does not mean we want to be treated like a convenient way to scratch your itch. There is a woman under the strap-on.

Let's go back to pegging not being like bowling. Pegging is sex. Sex with all of it's naked, intimate, vulnerable penetrations and entwining. And actually, it's even more than that because of the role reversal. The openness and vulnerability required for penetration...the skill and intention necessary to penetrate someone. Both are unfamiliar roles for the gender experiencing them. Pegging completely switches it up and things can feel pretty different, intense and intimate. Not usually a place most women want to go with someone they barely know.

That doesn't mean every one of us need there to be the possibility of a long term relationship, but it does mean we need there to be something that makes us WANT to peg you. Something that makes the moment hot and steamy. Something that makes us want to jump you and do you. Something more than 20 words in a pegging ad. Which leads us to...


Women Who Are Into Casual Pegging

You can find stories about women posting on Craig's List who want to try pegging with a stranger. You can find stories about pegging parties where there were a few women with strap-ons doing the guys. Are these stories true? Probably. But are these situations common? Absolutely not. They are extremely rare. Out of the thousands of pegging ads posted on whatever website you guys can find to post them on, an infinitesimally small number of men actually get a response, much less actually get pegged. Pegging ads do not work.

The exception is...If a woman is into casual play and the guy is a total hottie or charming, fun, personable or clever enough - she might go for it.  There are so many men begging for a pegging that women like that have a lot of men to choose from, though.

There are some women who would consider doing it for fun with a kinky friend.  But first you have to make friends with those women! If online - Making friends is most decidedly not writing to her and saying "Hey - I'm a virgin and I'm looking for someone to fuck my hungry ass. Interested?" Your messages will get summarily deleted. You must send a letter of introduction as I described above, meet her and get to know her first.


Kink Clubs

This brings us to in person. Where do these rare women who love pegging and might consider casual play...where do they congregate in person? The only place I know of is the kink community. The BDSM groups that get together in your area likely have a few women who are interested in pegging. The women in BDSM groups are usually more open about sex, too.

You can find groups in your area by going to FetLife.com and joining (free). Keep in mind that people in those groups have all kinds of kinks, so check your judgment at the door. You go to their public get-togethers, get to know people in the community and make friends. There is no short cut. One you have gotten to know the women in the group, you can try this approach. You lean in close to a woman you know and say, "Just wanted you to know that if you ever wanted to fuck my ass I would be totally down with that." She might laugh and tell you to fuck off. But she might call you later and ask you about it, too! People in BDSM clubs are experimental, and there is less of an emphasis on necessary intimacy when playing with others. Sometimes they just want to try something out. You could get lucky. But again - there is no shortcut.


No Whiners

So after all this...I hope I have not discouraged you men from exploring pegging. The only thing I hope I have discouraged you from is whining about how hard it is to find a complete stranger to fuck your ass. I have said it before and I will say it again: Pegging is like the Dubai Tower of sex thrills. It is exotic, deep, intense and explosive. For an experience that fine, that rich with pleasure and discovery...you will just have to work for it.


Ruby Ryder


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11 Responses to “I Need a Woman to Peg Me!”

  1. Dave says:

    Thanks for the lecture, Ruby. Fortunately, I’m married to a woman who is very GGG, as Dan Savage defines it, so pegging is just one of the things we do.

    The only additional word I’d like to add to your article is, “pro.” In every big American city I can think of there are professional escorts who offer all kinds of “kinky” sex, including pegging. Typically, it is referred to as “toy play” or “strap-on.” Men challenged by the dating scene might want to try that option.

    • Ruby says:

      I love the comments you leave, Dave. You make me think and sometimes fill in the blanks I inadvertently leave.

      I know men who have had wonderful, satisfying experiences going to a pro for pegging. And as Dan Savage says – sex workers really appreciate clean, respectful clients who know what they want. Going to a professional to experience pegging is indeed a viable option, and one I have recommended many times here, here and here. But I forgot this time! When it was really important…

      I suspect I really needed to include discussion of the pro option to soften the ‘lecture’. :-/ I come off kind of frustrated and bitchy. Both of which I cop to feeling! I wrote this so that I can refer all the guys who complain here to read about why that’s their reality. There are also men who while lamenting the lack of women interested in pegging, they don’t come off as indignantly deserving like the complainers.

      As much as I would like to wave a magic wand and create thousands of women who love pegging, I cannot. What I am doing is trying to educate women. I try to teach them about the thrills and pleasures of pegging, correct their misconceptions and allay their fears.

      The tide will turn eventually. But I don’t think it will turn to the point where women want to peg strangers. That’s precisely why professionals are an awesome option!

  2. Greg says:

    are there actually any pegging dating sites out there? Wish there were women who really loved to do that to their men. Be great if stimulated them as well while we are getting plugged.

    • Ruby says:

      (Please forgive my initial answer – I neglected to pay attention to where you posted this comment.)

      As far as there being dating sites that specialize in pegging – there are a couple but no one is claiming any measure of success that they can indeed help you to find a woman who is into pegging. For example – if you go to SocialPegging.com and try a search for a woman in a 200 mile radius in the general LA area, you get 6 results. Six!! And that is without any other delineating factors such as smoking, drinking, age, religion, etc. PeggingDating.com is the only other one I know of and seems to be the same kind of thing. There are no reviews, no success stories…pretty much nothing.

      I would actually urge men not to sign up for either of those sites and instead, try your luck finding an open minded woman. In other words, keep looking for a woman to date and just ask her relatively early if she would consider pegging. Or you can do what one man did and try to turn a vanilla woman into a pegger. This has worked for him!

      If you are not looking for a relationship – than go find a pro to help you.

      As far as your mention about women receiving pleasure from the pegging act – oh yes we do! We may not all be able to have an orgasm while pegging but that doesn’t mean we are not having a lovely time and are dripping when we are done (speaking for myself here, too…lol).

      And you can rest assured that there are women out there who do indeed love to use a strap-on on their man. Yes indeed!

  3. Monk says:

    tried pegging a few times with my wife who passed away several years ago. We were pretty clumsy and we never really got it going. Though I’m dating now, I like the advice of using a pro, because I’m not even sure I’ll like it, much less asking a GF to indulge in something so intimate.

    • Ruby says:

      Exactly. And pros who do offer pegging as part of their services are happy to find a respectful, clean, pleasant client, I’m sure. It can be a great way to check out pegging.

  4. Bill says:

    I think the ultimate aspiration for all of us into pegging, is to become ‘pros’ ourselves. There are elegant methods and the quick and dirty ones. If men are too impatient too nurture a relationship to their inevitable pegging aspirations, there are plenty of devices to quell the burning desire temporarily. Some of the best experiences in life rely on some form of denial before they can be fully appreciated. Besides, once you find the ideal partner, they will far exceed your fantasies.

    • Ruby says:

      Some of the best experiences in life rely on some form of denial before they can be fully appreciated.

      I completely agree with you here, though it runs at odds with the instant gratification way of thinking. Good things are worth working for. Relationships, pegging, gourmet meals, etc.!

  5. starkem says:

    Thank you for this sanctuary for the pegging community RubyRyder. As small, obscure and insignificant as it may be in the larger world of issues and activities, it does indeed feel like home for an open exchange of ideas on the joys of pegging.

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