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. And this, too.

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. Total long shot.

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 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



  1. You make sense but it still sounds difficult
    And thank you for the advice

  2. Looking forward to meeting girl who like to things out side the box ..

  3. i dont mind waiting for the women

  4. You make some good points in this article, which don’t apply just to the club of pegging-starved salivating man-dogs that some of us belong to.

    For those of us fortunate enough to live in countries where sexual services are readily available for payment, the question of “Where can I find a woman to peg me?” is a non-issue. The answer here is that you can find a woman just about everywhere to peg you. If one’s moral compass does not permit this, I can’t help but shake my head at the supposed morality of (subtly) manipulating a woman selected as the “target” with charm, wit, humour, and whatever else it takes (including time) to get her to don the strap-on.

    “Why is it so hard to find a woman who likes pegging?” – You make some good points here, and might I add, just because she might have sex with you does not mean that she will peg you. In for a penny, in for a pound? I think not. You even say that in a later section.

    “Pegging is Not Bowling” – True, but both are social activities that involve assholes, and in my opinion, bowling involves a lot more fucking about. I hate bowling by the way. I don’t agree with the elevated pedestal that the act of sex has been placed on, but I accept that there are people out there who see it the same way.

    “How to Approach a Woman” – I couldn’t help but think of the similarities between what you wrote in the first paragraph and Andrew Dice Clay’s “Three Beautiful Dates” routine. Of course, he was being sleazy and demeaningly manipulative for comic effect, whereas you’re quite serious. I loved what you said in the second paragraph though, and figure that what’s good for the gander is good for the goose too. I explain further in the next section.

    “Women Want to Be Treated Like People” – Abso-fucking-lutely. I totally get this, especially every time I’ve been asked by a woman to fix her computer (for free of course) after she finds out that’s what I do to earn a living. Does she see the man behind the Data Recovery Utilities Disk? No. Does she try to get to know me first? No. Does she ask me about what I might want? No. However, unlike what you said about dropping someone like a hot potatoe in such a situation, I try to educate, by taking on the request for assistance and making the situation with the computer even worse than it was. I’d like to think I’m succeeding in my attempts to educate, because I’ve never been asked for such assistance a second time, but it’s impossible to be sure. It’s fun for me to give someone a humanity lesson though. The double standard is very much alive and well, with both sexes. Both should deal with it, but won’t. Not as long as the act of sex (and in my case, the act of computer repair) is given special consideration.

    “No Whiners” – I think you’ve done a very good job with the article, and I think that everyone who reads it and is searching for a pegging partner will undergo a transformation of sorts. Hopefully, there will be a not-insignificant number of men who will realise that Life Is Too Short(TM) and that attitudes need to change. The fact that it’s much easier to change their own attitude, rather than trying to get others to change theirs, will hopefully allow them to experience pegging success sooner.

    I appreciate the opportunity you’ve afforded your readers to make comment, and also appreciate the time and effort you put into writing your articles on this wonderful subject. Keep up the good work.

    • Hi Harry – I am going to read a bit of this on my podcast – love your comments!! Remind me never to ask you for free computer work 😉

      • A “bit of this”? Hells Bells, you read the whole thing! I left a comment on the page for Podcast #92 at your site, and thought I should post it here as well so that it isn’t too disjointed.

        I never expected that the comment would be read out in the podcast, and I feel that at least one of the points I was trying to make may not have come through as I wanted it to.

        Ladies, please try and understand that for a percentage of us who are burdened with a single X chromosome, the knowledge that you Peg is an extremely high factor of attraction. If it didn’t feel so damn good, we wouldn’t give a rat’s ass about it, but it does, so we do. Continue to condemn us if you must when we don’t see the bigger picture that is You, but try to understand that it comes from a not-altogether bad place.

  5. Okay. Maybe this post isn’t aimed at people like me, and I don’t find it hard to believe that there are plenty of people who do deserve this kind of response to their chosen approach to dating. That said, I feel that there are some important points which are not addressed in this article, and which really do need to be, at the very least, acknowledged.

    Some guys who enjoy being on the receiving end, actually want it within the context of a loving, caring, mutually satisfying relationship. We don’t want no-strings sex, and in fact for some of us, the lack of an intimate emotional bond actually precludes anything even approaching sex. But even the bold among us can find it extremely difficult to find a woman who is interested in pegging, because in the past we have been rejected – or worse, humiliated – by a long string of women who do not share that interest.

    In contrast, it seems like the advice given in the article could be paraphrased as “If your date brings up pegging, be grateful. But don’t ever bring it up yourself, because nobody cares what *you* want. Just shut up and be happy she’s willing to consider dating you at all, and be grateful for whatever pittance she deigns to give you.”

    Seriously, this attitude is not going to help anyone.

    To provide an alternate suggestion, if pegging is something you want within a relationship, for men and women alike, I recommend considering disclosing this information early on. Yes it can, and often will result in rejection. A lot of people simply are not into pegging, and there’s nothing wrong with that. But at the least you will find out early whether the relationship has a chance of including a satisfactory sex life, and in cases where it is not, you will waste less of the other person’s time, and minimise the risk of causing and suffering the emotional fallout from spending months or years putting effort into a relationship that ultimately has no possibility of being sexually fulfilling for one or both of you.

    Above all, treat other people with respect, no matter what their personal opinions or sexual tastes might be. Even aside from the fact that it’s the nice thing to do, they just might be able to help you find your ideal match. 🙂

  6. I appreciate everything that you have said about treating people with respect and I still have patience…

  7. Where is the best place to find guys that want to be pegged? More so a submissive guy who wants to be pegged. I’m really just looking for casual NSA pegging

    • would be the best place to find what you are looking for. Just be prepared to be besieged! There are many, many submissive men on FetLife who would love to find a women who wants to engage in pegging on a NSA basis. Have fun!

    • Well, ‘just a chick’, I can agree with Ruby Ryder. There are plenty out there who want that, and well me being one of them! But good luck in finding what it is you are looking for.

    • Jarika Cardwell

      I’m not really submissive, but I like it when a woman gives me a good ass pegging and she really likes doing it

    • I would like to try it . I experienced things when i was a teen . So i think i might could do it

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