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


24 Responses

  1. 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.

    1. 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. 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.

    1. (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. 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.

    1. 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. 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.

    1. 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. 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.

  6. Dear Ruby,

    Thank you Ruby for all that you wrote, it is very interesting and quite rare to have found someone who has such a unique view on Pegging/Toy-play/Strap-on love making. I’ve had the pleasure of experiencing pegging for over 26 years, way before it even had a name or a following. Anal sex in general is still taboo subject in most circles let alone pegging.

    I loved your article Mrs. Ruby, it was nice to read something written about this subject matter that didn’t have the word ‘Rape’ or ‘Forced anal’ attached to it. I would like to add some advice for you and your followers though. Throughout my life I have discovered that this topic can make or break a relationship. After several attempts of sharing this side of my sexuality with respective partners it unfortunately ending soon there after. You are so right to say that this is a very sensual and powerfully erotic part of us. When someone leaves or might I even go so far as to say judges you for what your fetish’s are it is not exactly the greatest feeling. Please pay attention to your partners reactions to certain subject matters, I do not mean to discourage any of you ladies and gents. I am simply saying if your selected interest doesn’t like something as vanilla as wearing lingerie or changes the subject every time sex is brought up he or she is probably not the one.

    So my only advice is to be careful in who you do trust; I completely agree with you on several subjects you brought up about finding a woman to fulfill you sexual desires. At the same time I would like to point out that there are those beautiful wonderfully exotic ladies that seek their men as well. It had been my goal for years now to spread the Pegging life style and help others to find inner sexual being. So many are repressed and simply need a partner to love them unconditionally. Which unfortunately rarely happens in our pc society.

    I say this to all your readers, dedicated followers, and passer by’s like myself. He/She is out there and if you are patient enough and are truly a gentleman with not just a bulge in you pants; but with love in your heart to match your sexual craving she will not only find you…

    This woman will give you something that you’ve wanted since you took your first breath. Freedom


  7. Dear Ruby

    Very well written article for those guys who are in search of getting pegged and don’t know how to approach women.

    Let me tell you briefly about my story and what it comes to my mind at the end, which is not necessary comes to all the guys.

    I’ve pegged by two women so far, who I met them through fetlife. Even though I like to indulge in pegging and I do know that these women are too, but for me it’s a big turn off if I initiate the subject. For me, it’s a bigger turn on, if she’s the one who’s more eager to bring it up and I follow the course. I know it sounds weird, but I take it this way as in regular vanilla sex, usually guy is the initiator and also the one who penetrates; in pegging woman is penetrating so she has to initiate, well that’s kind of how it goes through my mind as I need to be the passive partner in pegging. Or you can say that there is an element of domination also plays a role, that’s why I don’t need to bring up the subject as she’s the one in control and play by her rules.

    One more thing which bugs me when I was reading the article, that these guys when they form the relationship because they need to be pegged, and they don’t mention on their first date, which I agree; but sounds like it’s a kind of hidden agenda. Let’s say after having the relationship going on and the woman says that she doesn’t want to do pegging; so this guy would break the relationship? Because for him that was the foundation of the relationship even though she was thinking that he’s there for her. That’s real a heart breaking situation.

    So after reading this article, please don’t get me wrong, it’s an excellent article for those who are naive, but I think there is something missing, which I don’t know what. But I know you will find and address. I personally think that these guys should go to Pro rather than looking for relationship.

    I can just say what I think, that I’d never break the relationship if I really do love her even though she’s not into pegging.

    1. Calling it a hidden agenda kind of implies less than honest intent. I don’t see it that way. Revealing is not without risk. Laying your kink cards out on the table is a dicey proposition for many men. Does this woman know your community? If you tell her you love pegging right away, will she tell the people you know if she decides not to date you? Much could be lost in that situation. Then again, waiting too long is not advisable because you get emotionally involved and then if she says no, it sucks. That is the heartbreak situation you describe.

      If pegging is a deal breaker and a guy must have it, then laying the kink cards down very early is called for. The earlier you discover whether your potential partner is down with pegging, the better. Nothing invested, easier to say thanks but no thanks.

      Most men who are into pegging have a stronger need to have it be a part of their sex lives than it sounds like you do. Sounds like you would be content without it. Not all men feel that way. In fact I would guess the majority feel opposite – they really need it.

  8. Hi Ruby,
    Yes your right about most men, well at least with me. I get so horny all the time and I love to take it up the ass!!!
    I have been pegged by a few good women and I would like to say, nothing feels better , what makes it exciting is when she straps on a very large dildo. I have been pegged with a dildo called the Superstar 16″ Light dildo, have you ever heard of it? It is 16″ long , 13.25″ insertable and 2.9″ wide, the whole shaft is 2.9″ all the way down, with a ripple like texture that feels really awesome, the faster it goes in and out , the faster it feels.

    I prefer to be on all fours and my ass up high at the corner of the bed so she comes up from behind me and she starts out rubbing Cleanstream anal lube and boy butter all over my ass , fingering my sphincter with lube , stuffing it inside my hungry hole, she coats the long dildo down and slips the head in, all I can tell her is the words ” fuck me !!!! “. ” harder !!! Faster !!!! ” and she gave me my wish , she slides the whole dildo inside me , it felt so good , for me , it’s easier to take a lot more cock when I’m on all fours, I’m able to relax my insides more to where the dildo will slide in deeper. I love taking in giant cock, since she stopped pegging me , I don’t have a choice but to do it solo, I bought a fucking machine and drill small holes in my big long dildos for the vac u loc attachment. The machine I have is very strong and can handle 5 to 10 lb. dildos, I made sure of that. It puts it an adujustable 1″ to 8″ stroke and puts out 250 strokes per minute. I have taken in some very large dildos on it, it’s very intense , I think it would be even more intense to have a woman strap me down on a table and set up the machine where she has the controls and she can plow the living hell out of my big pussy while she starts pulling on my cock , milking all my cum juice out.
    I love kinky kinky sex, I’m sure I’m not the only one either. Lol
    Anyone can please comment on this if the have a question:)

    1. From our resident size king who loves to wax poetic about taking big cocks and I suspect you wax poetic about it because it gets you off to share all this!
      I have some comments you might not like, however…

      First – I would NEVER advise the desensitizing lube you use – numbing lube is not a good choice because it eliminates your bodies ability to let you know when things aren’t right. Pain is an indicator! Besides, if you like the pressure and sensation of the toy against your prostate, why would you want to use anything to possibly numb that?

      Second – though I realize that the selection of enormous toys is not as large (pun intended) as you size kings and queens would like, that’s a pretty bad toy you are using. You have to search quite a bit to even find what they say the material is that it is made from – PVC.
      Just…NO! PVC is toxic and porous!

      Here’s a quote from a reviewer of Amazon:

      The rubber solvent smell was pretty bad when it first came out of the packaging but has mostly dissipated in just a couple of weeks.

      Any toy that has an odor is not a body safe toy. And though I realize that buying 100% silicone toys of that size can be quite expensive – I worry about the toxins you are taking into your body and the possible bacteria that the toys harbors (PVC toys are porous, and not sterilizable).
      Here’s a couple of options:
      Tantus Hoss
      Tantus Amsterdam

      Butt (heh heh) keep on having fun and playing with your big toys!

      1. Hi Ruby,
        I would first like to say, I don’t get off on how I write about how I love to take huge cocks up the ass. I’m just merely telling the truth about how I feel, it’s all true, no lies, I promise, that’s for sure. Hope you believe that , maybe it’s how I express myself, i hope I haven’t offended you or anyone else.

        As far as lube, the lubes I use might have a very small amount of desensitizing agent but believe me, I can feel the dildos as they slide inside me, trust me , I would never do anything to injure myself. I have been playing with big anal toys for years, I started out small just like everyone else, it’s very addictive, I will say this for a lot of men, not just me. The small dildos just tease me when I was using them. It’s kinda weird, not sure how to say this but a anus or asshole gets greedy or hungry so to speak wanting bigger ones up to an extent, highly addictive . I would never try a dildo wider than 4″ and even 4″ is pretty dam big but I can only take in a 4″ wide cock after a week of serious anal play with smaller ones that are 3″-3.75″ wide and only then I have to hurry up and pull out of the smaller one and go down on the four incher and sometimes it will slide in pretty easily and when it does , omfg, I can’t describe how good it feels, it gives me a pleasurable head rush sensation through my whole body. When it does go in , I try to leave it in as long as I can which is 5 to 10 mins. I have 2 really big 4″ wide 16″ long dildos, they are beasts, you should see them , very lovely giants!!! If it comes close to sliding in then I just keep using a smaller one for a little while and eventually I can take them. The dildos might be harmful, who knows but so is everything else in this world, I don’t think they are is bad as people think. Mine are high quality, not just some cheep stuff off of amazon. Lol. I have heard that they sell imitation products.

        I have been thinking about getting another custom dildo made out of glass from passionglass, he says he can make a very big double dildo with two different size heads 3.5″ – 3.75″ with a nubby thick 3″ shaft but it will cost a very big price.
        I looked at the Tantus Hoss , it only has a 2.75″ head, , if it was 3.25″ – 3.75″ then I would have to buy it , I bet it would be an awesome fuck. If they ever make a bigger one Ruby, please inform me about it.
        I’m just a normal person with a lot of kink , over the years as I get older I realize that if I’m going to have any kind of fun that have to go ahead and go for it.

        If anyone would like to chat with me or see my big toys go to fertile.com and open up free account and message me on there, my name is giantcockfuck. Ruby you too now if you desire 🙂

        I love chatting with you Ruby????

  9. I remember my first time, and it was nerve racking at first but the woman I was with respected me and slowly worked me up to it. I never believed I would enjoy it but I did. My problem now is my current relationship with this girl I am absolutely in love with, is very conservative when it comes to experimenting. She said she would do it for me but that is not the reason I want her to. I want her to want to do it. She understands it is something I am really into but I can tell she is not fully into it. She has played with dildos on me but it is the whole strap-on part that she is uncertain about. I would really appreciate some advice on the situation.

  10. It’s true it isn’t always easy to find a woman to peg
    Down the line it’s all about communication , and finding the right kinky lady 😉

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