The Epic Fail of Pegging Ads

Anyone who is the slightest bit interested in pegging, interested enough to search the internet a bit for more information has seen them.

Pegging personal ads, all placed by men.

From the restrained:

Anyone in Atlanta area interested in an "virgin" guy? 42 Caucasian, attractive, good shape, clean. Teach me!

To the simple:

I would like me a woman/women with strap on play.

To the crude:

Any women in the San Diego area want a hole to fuck?

To the playful:

Yay! strap-ons. =)
I like em big, girls, got one? You can borrow mine.

Just about any forum that talks about pegging soon gets overrun with pegging personals unless there is a moderator who has a rule against them and runs a tight ship. It is annoying. It is frustrating. But here's what makes it even more frustrating, for all parties involved...

It is a complete waste of time.

I don't care much for absolutes. So I'm sure, somewhere, there are a couple of men who have actually gotten pegged from placing a pegging ad. What is the percentage? I'd guess 99.9% of all pegging personals never see any action from their ad. At all. Yet men continue to place them, anywhere and everywhere they can. Just in case, maybe.

Let's look at the reasons why pegging ads do not work...

Here is one. Pegging is sex. Let me repeat that: Pegging is sex. So...basically these ads are saying, I really want to have sex, and I'm totally ready, so any interested women out there, hit me up! Um...yeah, right. Not gonna happen.

Here's another reason pegging ads don't work. Pegging is not very widely accepted by women who don't know anything about it. They have to get past so many potential fears! The fear that he's gay, the whole anal thing, the fear of pegging affecting their femininity, the fear of pegging affecting his masculinity, the fear that it will hurt him, the fear of not being good at it, the fear that he will get addicted to it. etc. So pegging ads do nothing to educate women about these misconceptions. Pegging ads usually just say, "Wanna fuck me?" Again, not gonna happen.

And another reason. The odds are way against you. You are drawing from a very small pool. The number of women who know about pegging, think it rocks, love doing it to guys and have their own equipment...is really quite small. We are out there, here and there. Included are women who no longer are with the partner who introduced them to it but still really want to incorporate pegging into their next relationship. Still - even combining those groups - not very many women. This group of not very many women...yeah, well, we get a tad besieged by the throngs of men who want their ass fucked. We usually get approached (via private messages or crude comments in a thread) in a way that is all about the strap-on and not at all about us as people, which goes over like a burnt piece of toast.

And one more reason. Pegging is intimate. I know pro dommes who will not do pegging because it is too intimate! Take the normal intimacy level of regular PIV (penis in vagina) sex. Multiply it a couple times, at least. Why? You've got role reversal going on, which places both partners in situations they have never been in before. That's a vulnerable position to be in and requires trust. A lot of it. So the likelihood that an ad asking for a woman who wants to fuck a guy's ass is going to work? Again...not gonna happen.

So...what's the harm in putting up an ad? I'll tell you. By asking for it all over the place - you guys could possibly be further ensuring you will not get it. Unintended consequences.

Here's why: If a man approaches me with a polite, forthcoming, articulate message that does not go on and on about how much he wants me to fuck him with my strap-on, I check him out and look at his comments in other areas on the website that we are both on. If I find that he has a habit of leaving pegging ads all over the place in groups, or messages on women's walls or photos (who are interested in strap-on play) like, "I'd really like you to fuck me. I'm bent over and ready", I cross him off my list right then and there. Because the strap-on is obviously the focus, not the woman. I have no interest in that kind of connection. Are there women who might be interested? Not so much. In my travels I have encountered a couple of non-pros who would be interested in a strap-on experience and not a relationship. One asks for donations...and the other wants to film you. Not that these are bad - just...for profit.

I've said it before and I will keep saying it. If you are just looking to experiment with pegging and you do not want a relationship, go find a pro. If you are looking for a relationship with a woman who enjoys pegging, you can look for that interest on the woman's profile and send her a polite, forthcoming and articulate letter of introduction (without mentioning the pegging!). Or, you can look for a relationship with a sexually open-minded woman in the way you normally would, and attempt to introduce her to pegging later. Here's one man's story about how he did it.

I am not without sympathy for you men. It is a big step to decide that you want to be pegged. And if you have indulged in any anal play, you know how good it can feel. And you want it. Passionately. But I urge you...knock off the personal ads!! Try methods that have a greater success rate...please!

9/15/15 Note - Back when I wrote this article, I did not leave enough space for the possibility that pegging can indeed be experienced without intimacy, in a variety of situations. Basically I was projecting my own experience onto everyone else and coming from a space of reactivity. What can I say except - Oops! Also - There is a bit of a shaming tone here that I have recognized (and been called out on) since posting this. I'm not going to edit it out or delete the post, but wanted to acknowledge it and apologize.

Addendum: Intimacy is often a factor in pegging. However, this certainly does not apply to everyone. There are people who can practice pegging with a casual hookup, and may even prefer to. Perhaps there are some parallels here to regular PIV (penis in vagina) sex, which can be engaged in either in a more casual, for fun type of manner, or can be deeply emotional and intimate - depending on the connection of the couple involved. Exploring pegging with a professional has its limitations regarding intimacy as well, for obvious reasons. And there are a variety of other kinky scenarios where intimacy is not a part of the desired experience for either partner. The way you choose to experience pegging is truly up to you and your partner. There is no one way.

Read more about this here.

11 Responses

  1. EXCELLENT! Very well said! I was just having a very similar conversation with my spouse just last night. I wanted to ask, what these men really get out of leaving ads like this, or unsolicited email requests? Some pipe up during every pegging conversation on some boards saying, “I’ve never been pegged, hit me up.” or something similar that has absolutely NOTHING to do with the current discussion. While I feel for their plight, it really just is very annoying and quite pathetic.
    Keep up the good work (writing) Ruby! You ROCK!
    MK

  2. Mark – You are welcome. I am doing well and hope you are, too.

    @Mistress_Kim – I so appreciate your kind words. Thanks. The annoying factor I see we both experience! And like you, I feel for their plight. But not enough to let them think that their ads garner anything more than annoyance and derision, sadly. Time for a game change, guys!

  3. I couldn’t agree more with the above comments. It also bothers me when people seem to want a partner for 1 specific thing, such as pegging. What about compatibility, trust etc… I’d given up on pegging with my current partner despite it being something I’d enjoyed in the past as she just didn’t like anything anal on her. Why? Because I liked her, I wanted to spend my time with her, all that “boring” stuff. I came across your website, I thought we’d have an open and honest discussion. Now we’re peggers. Turns out it was just her ass she didn’t like touched, more than happy to go to town on mine. What worked for me, finding someone I respected and liked for who they are, not what they would do.
    Sorry for the long post, and thanks Ruby!

    1. I received a message some time ago from a woman who took me to task for my assertion that ass play with the woman might be the only lead-in to pegging for the man. She was like your partner; not at all interested in ass play herself but happy to oblige her partner with a good pegging. Certainly the desire for ass play does not have to be mutual and sometimes definitely won’t be. But that doesn’t mean all is lost in the land of pegging!
      Thanks for sharing your story.

  4. I came across this article randomly and couldn’t agree more. As a woman who is most definitely interested in pegging,but has never done it, the emails from guys are very off putting. I completely agree with earlier post. I would love to find a guy that I click with and enjoy spending my time with that also happens to want to like or wants to explore pegging. Its not a must have just an added bonus. But the emails of “my wife is close-minded so you wanna meet up?” are not a turn on.

  5. I’d like to add to this great article: horny and desperate men could be potentially dangerous. A lot of the times they turn out to be rude and demanding. And men are generally stronger than women. So as far as I am concerned even if I really really really want to have sex (pegging or not) and I’m single, I still would never ever reply to a sex ad, as I don’t want to be offended or raped. Sex ads are objectifying to women and if men don’t see us as equal real people – we are in potential danger.

    1. As a woman, I am quite familiar with the element and sensation of potential danger when meeting any man for the first time. As a result – I have never responded to a sex ad. But I know women who have, and have had a fabulous time of it.
      I enjoy objectifying men from time to time, so I know that side of things as well. It’s not always a bad, dangerous thing. There are men – and women – out there who enjoy the experience of casual sex.

  6. I run a pegging group in Houston. My fet life page does not permit personal ads for this exact reason. They just don’t work! We have munch where people get together meet and get to know each other. People want to come to our parties that have not been to a munch. I discourage this.
    ery few women are willing to play with a man that they have not establish some sort of relationship with. I have been called many things, most recently a douche, because I don’t permit personal ads. My group I’m gonna run of my way.

    1. Right? I suppose the level of desire and frustration and desperation regarding finding a pegging partner is what drives receivers to post ads, even though there have been MANY observations that they just do NOT work for more than the occasional .5%.

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