newryder7

Podcast: For the Ladies

I have been recording podcasts for some time, but this last one might be of particular interest to you.

For a while now I’ve been working on a book, a short and read-in-one-sitting book, in my voice, that was specifically intended for men to give to their partners to introduce them to the concept of pegging. I’d pretty much finished it, but I changed my mind.

I made it a free podcast instead. I decided that I wanted it to be available to anyone that wanted/needed it instead of being something they had to pay for on Amazon (my original plan). Because, basically my goal is to facilitate as many couples understanding and enjoying pegging as possible. Especially the women!

And I think this might help.

Men could introduce the basic concept to their partners and then direct them to the podcast and say “listen to this”.

I address the common misconceptions and fears, hold space for those who decide it’s just not their thing as well as those who decide to embrace it, and through it all, emphasize over and over again that it took a ton of courage for you guys to approach them, and it is truly a gift of intimacy. Because you are allowing them to know a deeper part of you, no matter how they decide to respond. I encourage communication over and over, because good communication about sex is indeed the sexiest thing out there!

For those who are interested – could you give it a listen and let me know what you think? Feedback? Did I miss anything important? Criticisms?

Podcast is 50 minutes in length and you can stream it directly from my other website. Click the link under the photo above.

 

 

Pegging 101 Interview Podcast #1

You’ve all heard me talk about going to a sex worker as an option for those men who really want to try out pegging and cannot find a partner to try it with.  This man did it! And called me up to tell me the story. Give a listen – it might just change your mind a little about going to a professional…

 

If you are a man who wants to approach your woman about pegging this article is for you.

(If you are a woman who wants to approach your man about pegging, click here.)

 

http://isissandosiriss.tumblr.com/image/28677070563

http://isissandosiriss.tumblr.com/image/28677070563

Podcast #112 – For the Ladies

Update: I recorded the above podcast specifically for the circumstances where you have just introduced your partner to the concept of pegging. The podcast is in my voice, talking to her. I offer accurate information, dispel myths and misconceptions, and emphasize the health of the relationship above all. I don’t try to persuade, I inform, and verbally hold space for those who decide it’s not their thing. Please listen to it first before sharing it with your partner, because only you can decide whether it’s appropriate for her!

I Don’t Want Her to Think I’m a Freak

For you gentlemen who have an established relationship and you want more than anything to convince your partner to peg you…what is the best way to do this? How can you approach your lady…and let her know that pegging is what you fantasize about, dream about…that you’d like nothing more than to have her slide a smooth silicone cock slowly up your ass? And how can you get this idea across without her thinking…you are a freak/gay/twisted/weird? I will do my very best to try and help you here…but please realize there are many contributing factors. While some of you may be able to just casually mention your interest and quickly find yourselves shopping for the right dildo, others will find that despite their best efforts, their partner won’t consider pegging…at all, period, end of discussion, case closed. But let us remain hopeful…


Communication and GGG

First, communication is the key. You need to be able to ask for what you want. If you can’t open your mouth and talk with your partner about sex, she is not going to magically intuit that you want to get fucked up the ass with a dildo. If you demand instead of ask…that’s not likely to meet with any success, either. Take a good long look at your relationship first. Do your very best to practice Dan Savage‘s GGG – Good, Giving and Game. “Think ‘good in bed,’ ‘giving equal time and equal pleasure,’ and ‘game for anything—within reason.'” If you just want to find one more way to please yourself and you don’t really give a flying fuck about her pleasure, don’t bother asking for anything until you get your act together…seriously. We are not just talking about your lady’s willingness to peg you…we are also talking about the state of your relationship with her…Think about it. Make sure you take into consideration her state of mind and whether she is stressed out with time demands, work, children, etc. Do your best to alleviate her stress and make sure you contribute equally to the relationship.

If you are indeed GGG and think you have a partner who is so open to new things while remaining unaffected by misconceptions and stereotypes that you can just tell her straight away that you would like to try pegging, by all means go for it. Some men actually have success this way! But be forewarned that you may also put her off the idea for good. Big risk. If you even get a hint that any part of her will be reticent about the idea for whatever reason she may have, I’d advise using a different, more gradual approach. Keep reading.

 

Important – Do Not Ask For Strap-on Play Right Off!

Patience is the key here. Many women when asked for strap-on play right off the bat have refused because they have no idea what pleasure the prostate can bring. Also, they have nothing to counter the usual misconceptions connected with pegging. If those same men would have asked just for fingers to start with it’s likely that some of the women who refused would have indulged their men in an attempt to bring him pleasure and then discovered just how amazing it could be for their man. So remember, have patience and ask for fingers first. Bide your time.

Next, let’s divide your women into two general categories: those who accept anal stimulation themselves and those who don’t.

 

She’s Into Anal

If your lady has already shown a willingness to engage in anal play, you have a foot in the door. If she is willing to let you put a finger or toy or your cock in her ass, there is a much better chance she will consent to exploring yours. Tell her you can see she is enjoying it and you want to see what it feels like. Or…you read an article about prostate orgasms and want to experiment. Or you heard from a friend/read on the internet that men can have insanely powerful orgasms with a lot of come and you’d like to try it out just to see what happens!

 

She’s Not Into Anal

This is a more difficult category, guys. Maybe you have a woman who has always refused anything anal; you touch her anus and she flinches or pulls away. There can be a lot of reasons for this. Perhaps she was told as a child her anus is dirty and should never be touched. Perhaps she thinks that only sluts have anal sex. Perhaps she is a bit of a germaphobe. Maybe she’s just totally grossed out by anything to do with excrement. Or maybe it’s just as simple as she has not yet been able to open up and own her sexuality without being concerned about what other people think. Sometimes that comes with age. Any or all of these could be true. Or…it could also be true that no one has ever played with her ass before (including you) and she just doesn’t know how pleasurable it can be.

Be aware that there are women out there that just don’t like receiving any kind of anal – yet that does not preclude their interest in fucking you! So even if your partner is not into anal at all – she could still be an enthusiastic pegger. Receiving anal herself is not a requirement. So if your partner gladly slips a finger up your ass during a blow job but steadfastly refuses to let anything near her ass, this is still good news. Just skip down to Offer Another Trade.

 

For the woman who is not into anal, consider the following approaches and ideas:

Explore Her Ass First

Two ways to do this…only you know your partner well enough to know which one might work best.

1) Get her incredibly horny (oral, kissing, nipple play, etc.) and ask if you can please, please, please play with her ass. Put your pride aside and fucking beg, if that’s what it takes. Promise her that you will only use your lips, tongue (if you are into rimming) and one finger or a small toy; your cock is not going to come anywhere near her ass. Because that is the fear of many women – the ignorant and savage thrust of a cock up an ass as if it were a pussy has put many women off anal sex….forever. So you need to go at this ultra-slow. And no matter how tempting it is for you to slide your cock into her ass…don’t do it unless she asks for it! And even if she asks for it, continue to tease and play and open her up for a while until she’s begging for it and you can easily put 2 – 3 fingers inside her. If she doesn’t ask for it…do some ass play as foreplay and then fuck her vaginally. Afterward, wax poetic about how totally hot that was to play with her ass and you absolutely loved it. The idea here is to get her used to ass play in general before asking her to peg you…and to wake her ass up to the pleasure potential there. Important: while you are playing with her ass keep the communication lines open and keep asking her if she likes what you are doing as you try different things.

2) Discuss your desire to play with her ass when you are not in bed, when you are having some close together time. Ask her if she would be willing to let you play with her there…that you promise it won’t hurt and just the thought of it really gets you excited (and you swear you will absolutely not put your cock up her ass). Reassure her, if it seems necessary, that you will love and respect her no matter what you two do in bed, and you will attend to cleanliness issues in whatever way helps her to feel comfortable. If you are not into rimming or the thought of it grosses her out, fingers and small toys are fine…even a small toy that vibrates! If she agrees, proceed as described above. If she becomes receptive to anal play, consider anal beads and experiment with pulling the beads out at the moment of orgasm trick. Find out what she likes best – ask questions!

 

Offer a Trade

If she is reticent – offer a trade. Tell her that if she will let you play with her ass one night, you will do whatever she wants the next night. And be ready to fulfill any reasonable request of hers. This is all about mutual pleasure. If you can get her to enjoy anal play…it is much easier to introduce the concept of her exploring your ass. (If she refuses – see below “Show her How Good it Feels For You”.)

Once you have played with her ass several times very successfully (not necessarily even fucked it) you can try talking with her about how you would really like to know how ass play feels. You can see how much she is enjoying it, and you read/heard that orgasms for men can be insanely powerful with anal play. Don’t mention the strap-on yet. If she goes for it – excellent! If she is still reticent…

 

Offer Another Trade

Tell her you will trade her one night of pleasing her in whatever way she likes best (it’s all about her) for a night where she indulges you in some ass play (it’s all about you). Suggest that if there is something she’s wanted to try but hasn’t asked for yet, this would be a fine time to put it on the table, as you are very interested in pleasing her sexually in the way she wants to be pleased. And you’d like to explore your interests as well. Just be ready to put on the lace panties or paint her nails or whatever it is she wants. As long as it is not a hard limit – it would behoove you to indulge her…just as you are asking her to indulge you.

 

Resistant? Start Off Slow

Do not go straight to asking her to fuck you in the ass with a dildo! Too much, too fast. Tell her again that you have discovered/read/heard that ass play feels really good for men and you want to explore it with her. Have her try fingers first (gloves if she wants them), giving her nothing but positive feedback if she’s game. Pick out a plug together and ask her to put it in you to wear while you are fucking her or when she is giving you a blow job or hand job. (Invite her to wear it while you are fucking her, too!) Exclaim how amazing your orgasms are with the plug in and suggest you try other toys. Maybe at that point talk with her about strap-ons. Tell her, while looking into her eyes with the best smoking-hot look you can muster, that just the thought of her…wearing a strap-on and doing you…about sends you over the edge. Just the thought.


Choose Your Timing

Do not start a conversation like this when you are in the middle of having sex. Talk with your partner about this out of the bedroom. Otherwise she will feel pressured and believe me – you stand a really good chance of killing the mood…and killing your chances. Choose a time when she is relaxed, receptive and maybe even had a glass or two of wine. An incredibly important point here is that you need to be a partner who is responsive to her needs if you are asking her to be responsive to yours. Read that again and think about it…and if you are not that kind of partner, make those changes before you ask for pegging. Your woman needs to feel that you take very good care of her needs and desires in the bedroom. If she feels that way, she will be much more likely to give you what you are asking for.

 

Confidence

A friend of mine offered another very important point to keep in mind when you ask for what you want. Her words say it best.

“Women are like dogs in that we can smell fear….if, when you ask us to play with your ass, you are worried or nervous, we will sense it and think you’re asking for something weird. If you project confidence that you’re asking for something totally normal, we’re more likely to agree.” Strap-on Jo

 

You’re Gay?!…This Will Turn You Gay!!

Undoubtedly, some of you will encounter the “gay” reaction from your partner. So…

I am going to give you a few choices of what to say if she accuses you of being gay or worries that if she pegs you it will “turn” you gay.

  • “That’s silly, Honey. If fucking a guy in the ass with a dildo makes him gay…then fucking a lesbian with a strap-on will turn her straight!”

Okay, maybe you don’t talk this way…maybe you are at a fine restaurant and trying to have this conversation clandestinely. Here is a toned-down version:

  • “Don’t be silly, Darling. The area of my body that I enjoy having stimulated has no bearing whatsoever on the gender I prefer. I am completely, 100% straight, period. The only person I want playing with me…there…is you.”

Other options:

  • “Nope, I definitely prefer breasts with my strap-on. Would never let a guy near my ass. You got nothin’ to worry about, Babe.”
  • I am just interested in exploring whatever brings us pleasure, Honey…I haven’t switched camps!!”
  • Your pussy is the only thing I want to sink my cock into, and your strap-on is the only thing I am interested in having sunk into me.”

You can also show her or read to her “No, He’s Not Gay” where I go into this in more detail.

 

She’s Freaked Out by Wearing a Cock

I didn’t know this was an issue, because I never had any back off strapping on a dildo. Some women, however, have a real reaction to it. She may think it means she wants a cock and it freaks her out (tell her you know she doesn’t want a cock for real – this is just about using toys to play)…or it feels too much like role reversal and she is really not into that idea (tell her you have no interest in reversing roles…but you are interested in playing with toys)…or it’s just too awkward and she feels foolish (tell her trying something new often feels awkward and that’s okay – you will both figure it out). If your lady has played with your ass and is okay with that, leave the harness aside and let her use the dildo with her hand. Once she tries it she may warm up to the idea of strapping it on. She may not, but one can hope.

 

It’s Dirty

If she’s resistant because of the “dirty” idea, tell her you will prepare by giving yourself an enema and she can use gloves. You will do everything you can to be as clean as possible. This means not eating a lot of crap or drinking alcohol a few days before, too, because that will make your feces stink more than usual. Read “Keeping Things Clean” and take the advised steps to ensure a positive experience for both of you.

 

Do NOT Show Her the Porn

Whatever you do, do NOT show her your favorite porn clip of pegging! I say this because the vast majority of “professional” pegging porn includes aspects of humiliation, feminization and abuse. If you play that way – more power to you, but I suspect if you are here reading this article you have a partner that might be a little more vanilla. The very last thing you want is for her to see that porn showing a guy dressed up as a woman and being beaten while she taunts him and fucks him. Again – this is not a judgment about what turns you or your partner on. I am just saying be aware of what you are exposing her to and how she might react to it. Spend some time looking for a few hot amateur porn clips that are loving and gentle and the man is moaning in ecstasy. They are out there!

 

Show Her How Good it Feels For You

If she is completely unwilling to give or receive anal pleasure and you are not willing to live without it, go ahead and carefully lay your cards on the table that you are very interested in ass play yourself, even if she does not want her ass explored. Consider asking her if you can just put in a butt plug while you fuck her, just to see what it feels like. She won’t have to do anything; you put it in yourself (moan a little). When she sees/hears the intensity of your orgasm, she might be more curious and interested in checking out your ass. This works for women who are sincerely interested in giving their men pleasure. If she doesn’t give a hoot about your pleasure…I don’t have any magic words for you. Maybe call Dan Savage (sex advice columnist) to explore your options.

 

Warning! Read This Before You Act!

Men who would love to experience pegging have fears of expressing their desires, understandably. There are some men who never confess their fantasies much less try to turn them into reality because they are so afraid of or even certain of rejection. Indeed, with the taboo factor and society’s puerile judgment that if a man likes anything anal he must be gay, men’s fears are legitimate. I’m telling you this because you need to make sure your partner is trustworthy before you divulge your innermost sexual desires to them. Only you can make that judgment call. And I so wish I had a magic wand for you. On one hand I would love to see you guys let go of your fears and express your desires to your partner.

I have heard amazing stories of men who did just that and their women, after initial surprise, agreed to try it and ended up loving the feeling of fucking their husbands. I have heard stories of how it totally renewed the sexual spark in a relationship of many years. Yet I have also heard sad stories of women who called their husband gay and never fucked them again. Honestly, I just want to slap those women for being so sexually fucked up and for being so cruel to their husbands. So again…we come back to the point that your relationship needs to be solid, intimate, sexual, trusting, open and communicative. If divulging a yearning for pegging might destroy your relationship, you need to decide whether you can go the rest of your life not having your sexual needs met, whether you need to leave the relationship and find someone more sexually compatible or whether you can come to an agreement that you can get your needs met elsewhere. Tough questions.

 

A Request From Ruby

For those of you who have success with your ladies, do me a HUGE favor and ask her what it was exactly that convinced her to try it? Then write me an email and tell me! I want to know what persuades an initially reluctant woman to strap one on and learn to love fucking her man. And then I will do my very best to bring many more women around to the idea….because I know how much you all want it.

 

Gentlemen…I will keep your wanting and willing asses in my thoughts (that’s easy) and hope you all find yourselves enjoying a thorough pegging very soon.

 

Ruby Ryder

 

 

 

 


In the pegging world there are many men looking to explore pegging on a casual basis and not many women who are ready to sink it deep inside them outside the structure of a relationship. When I get letters from these men or find threads asking if there are any women who want to peg them I usually suggest the men either go to a professional or look for a relationship with a woman who is sexually open-minded and attempt to convince her to try it. The relationship route requires patience, dedication, timing and has no guarantee of success, sadly. And perhaps the man is not desirous of a relationship in his life; he just wants to try pegging.

When I suggest the option of a pro, I often see some variation of this response:

Never paid for sex in my life and not going to start. I don’t recommend anyone pay for something you can get for free.

Judgment about sex workers frustrates me. They rock.

But let’s explore this. Can a man find a partner who will peg him for free? Sure. Is it a difficult thing to do unless he is incredibly hot, single and awesome? Well, judging from all the posts on just about every pegging group that allows personals around the internet, I would say the answer to that is an unequivocal yes. Perhaps less difficult if you are from the younger generation (20’s) who seem to be more open-minded around pegging and sexuality in general. But still far from an easy task to accomplish. There are men on forum boards I frequent who have literally been looking for years without success.

Are there actually women out there who love to peg men and would enjoy a wild night of pegging with a relative stranger with no monies exchanging hands? Yes, there are a few here and there. They are exceedingly rare and are usually seeking out the incredibly hot, single and awesome men.

 

For a single man who has never tried pegging, let’s examine the comparison between going to a professional and trying to find a woman to peg him for free.

For Free

You can attempt to find a woman who is into pegging. You can approach a woman you have just met about pegging and possibly have her reject you as a result. You can worry about whether she will go and tell everyone in your social circles that you want to be fucked up the ass after she rejects you. (This may not be a concern for all of you, but if it is, it is a very real concern.)

You can feel uneasy about buying expensive equipment when you aren’t sure if you will even like pegging. You can wonder whether that equipment will fit her correctly and whether she will be able to have an orgasm, if she even wants to. You can worry about whether the steep learning curve will frustrate her and she will refuse to try it again after the first experience. You can hope that she will not hurt you, in her inexperience. And you can hope that the communication between you will be adequate to facilitate a good experience, because good communication is essential for pegging. And good communication takes time to develop.

Don’t mistake me here…experiencing the adventure of strap-on sex with a partner who you are already in a relationship with can be an amazingly life-changing experience. All of those equipment questions, the communication, the learning curve, the making sure you don’t get frustrated or hurt and both of you find pleasure are all still paths you will travel, but you have the foundation of a trusting, loving, communicative relationship to contain it all and help you find your way through any mis-adventures to the ecstasy. You do not have that foundation with a woman you just find and ask to peg you. You can certainly put your efforts towards finding a woman, starting a relationship with her and then asking her. But this option is only good for those men looking for a relationship.

I am not saying that experiencing pegging with a relative stranger never works; it can. But for all the reasons I have outlined, the odds are completely against you, unless you are incredibly hot, single and awesome.

The Professional

Consider the contrast of the professional experience. You contact her. She communicates with you (part of her job) to discover exactly what kind of experience you are looking for. Are you looking to combine a couple of other kinks with the pegging to enhance the experience? Are you completely new to anal play? She asks many questions to discern exactly what you need. She will give you instructions on how to prepare for your visit to her. When you go to see a professional, it is in her best interest to provide you with an optimum experience to the best of her ability so that you will be a satisfied customer and hopefully return or recommend her to others.

You do not have to worry about her inexperience or being rejected by her because of your desire for pegging. You do not need to be concerned about her pleasure or selecting (and paying for) the right equipment. You get to experience pegging for the first time…with someone who knows exactly what they are doing and wants you to have the best experience possible. She will keep your secrets, too!

Additionally, a professional is certainly likely to be more safe, clean and knowledgeable than the woman you met at a party who says sure, I’ll peg you! It’s her job. What professionals offer is the ability to tailor the experience to your desires and fantasies as well as the knowledge to make it happen safely and satisfyingly. You are paying them. It is an equitable exchange; a win-win as it were. Doesn’t that take the stress out of the equation and just let you relax and enjoy? Think about it.

With a professional, you can live out that pegging fantasy just the way you want. And if you discover that you like pegging, then you can bide your time and find a woman when the time is right and try to convince her to try it. Or, you can just continue to get your pegging with professionals and never seek out a relationship if that’s what you want.

I encourage all you “I need a woman to peg me!” guys to consider a professional. It is a valid option for men who want to explore the world of pegging apart from all the complicating factors of a relationship.

(And if you are married or partnered and you go to a professional sex worker – just don’t tell me about it! I tend to have an overemphasis on integrity and honesty and then the self-righteousness comes out…it’s not pretty.)

 

Lastly, to all you lovely sex workers out there:

Thank You.

…for everything you do, for all you know and for all you give.

You rock.

Gentlemen…

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.

 

Wow.

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 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

 

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 professional dominatrices 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!

 Ruby Ryder

Gentlemen…

Just so you know…there is no cache of women who are eagerly waiting to take the cherry of any offered up virgin ass that is craving a pegging. It simply does not work that way.

If you just want to experience pegging, go find a sex worker to help you. And I am serious about that. Sex workers would love to have a nice clean and respectful man who wants to experience pegging pay them for services. Depending on where you live in the world, it may even be legal.

If, instead, you are looking for a relationship with a woman who will peg you, then look for a woman in the way you would normally go about finding a partner.

If you want to be sure she’s into pegging before you date her, FetLife.com is free and will connect you with kinky folk in your area. The search capabilities are definitely limited, but I believe that helps to keep out the riffraff. You can find people in your area, but you have to take the time to look at each profile to see their kinks. (There are other dating websites that cost that will sort by kink – but I can’t recommend them.)

So let’s say you find a woman you are interested in, you’ve read her profile and determined she is available. The worst possible way you can approach her is to say – “wow, you are into pegging, will you do me?” Do you do that in all your relationships? “Wow – you are cute, can I fuck you?” No – you get to know her first!

Have some respect and manners in your approach. Send her a polite letter of introduction and engage her in conversation about something other than pegging. Meet with her over coffee, take her out to dinner. Get to know the woman, don’t just pursue the strap-on.

I feel for you, guys…and I’m honestly happy you are interested in pegging, but start thinking with your big head!

And don’t forget – it is indeed possible to turn an open-minded woman who has never done pegging into an enthusiastic pegger. I have heard many first hand accounts that bear this out! For some advice on how to do that, read this:

Approaching Her About Pegging

For one man’s story on how he turned a vanilla girlfriend into a pegger, read:

Vanilla to Pegger – One Man’s Story

Best of luck with your search, gentlemen.

Ruby Ryder

Thanks to my friend D for allowing me to post this piece. There are so many men out there who want it, need it and crave it. Here is one man’s suggestion on how to find a woman to peg you.

This is for all those guys who are begging for some random lady to bend you over. Here is how I did it.

I met a regular young vanilla girl on a very vanilla dating site. We went out on a date or two before we had sex. We talked about sex more and I made some comment about how young girls are prudes. She asked how? I said that they are not adventurous. So we talked about anal sex and eventually on date 4 or 5 we have anal sex and she loves it.

A few dates later I took her to a sex shop that just happened to be in the same parking lot as the restaurant we are ate dinner at (nod nod, wink wink). After dinner and a few drinks we walked around looking at all the lingerie, toys and videos. In the toy section I casually pointed out a strap-on and asked her if she would do a girl with it. She said no way, she is not into women. Later we have more regular sex.

Then we texted a lot about all sorts of sexual topics including blow jobs and prostate massage. She said she was unsure about fingers in the ass as her nails might scratch. At some point she put two and two together and asked what I thought of strap-ons. I played dumb and said I’d like to try it with her.

I sent her to www.take-it-like-a-man.com and she did some reading. We sent more texts about it to each other. I sent her to www.peggingparadise.com/blog and she read more. Along the way she had some reservations… like – is this the only sex I want? How often do I want to do this? Etc…. She said she wanted to try it but only because we were now in a relationship. We had been dating for a few months.

She was concerned that she may not like it and didn’t want to invest in the equipment. Lucky for her I already had my own equipment. She was ok with that…and the obvious fact that I had done it before. I assured her that everything was sterilized and clean. Our first time is using a regular strap-on dildo and she is very awkward at it. I get off and keep reassuring her how great it was. She wasn’t that into it the first time.

Then I let her borrow my Realdoe. It’s a double ended dildo and she likes the flesh color. She just happens to like watching porn so I sent her to www.xhamster.com and told her to search for strap-on scenes. She got to masturbate with the Realdoe for a few days before we saw each other again. It was important that she felt comfortable with the dildo and knew how to get pleasure from it.

The second time we were together for pegging,  she was much better at fucking me because she had warmed up to the idea and knew how much I liked it. Of course I was still pleasing her first sexually before she pegged me.

So that’s it, guys. You are not going to just find some random chick off the internet and say hey baby bend me over. Find a real woman to date or get your significant other to do it.

I have done this in my past 2 relationships and it blows the girls away to do something different and unique. It’s all in the delivery and it takes time and effort but it is so worth it.

Happy Pegging!

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

Yes, there are indeed many women who love pegging. All women are different and their specific reasons for enjoying strap-on sex are as many and varied as the individual women are. Some women enjoy pegging as another tender, sensual addition to sweet lovemaking. Some like to combine it with other kinks (and those are many and varied as well). Certain themes rise to the top when women talk about why they like pegging. The vulnerability of the man. The taboo aspect. The pleasure of running the show. The fascination of sexually switching places. The deepening of intimacy.

I most definitely love pegging. I know, no surprise there!

But what is it exactly that turns my crank when I don a strap-on and peg my guy? My, my, my…so many things.

The Pleasure Principle

More than any other reason, I love to peg a man because it brings him so much pleasure. Some time ago I had the privilege of introducing a new  lover to pegging. After he came exquisitely hard in his hand while I sunk deep inside him…he gasped, “I had no idea!” I love the cause and effect of watching a man’s body react when I thrust inside him. I love the moans and gasps I can elicit. Pegging allows me to actually be inside him giving him pleasure, which is a thrill in itself; the only time in sexual play that I get to do that. But mostly…I just love to put a man in ecstasy with my strap-on.

Open up, Baby

There is a vulnerability that is necessary for a man to be penetrated. I don’t really see that with vanilla sex. A softness in his face. His eyes become a little unfocused or they close. I love that vulnerability. I love to see a man purely receptive and open…it is a rare and beautiful sight. That vulnerability makes me want to gather him in my arms and fuck him sweetly and continuously until he comes with cries of passion.

Happy at the Helm

I love…running the fuck. I am in control. I can tease him…or pound him…until he begs for release or respite. I can change the angle of my toy just a bit and know it’s driving him crazy with pleasure. Or I can stay still, buried inside him and drive him crazy with wanting more. I am wearing the dildo, so I get to decide.

Forbidden Fruit

I love the taboo aspect of it. I mean, as taboo thrills go – fucking a man in the ass with a strap-on dildo is like the Dubai Tower of illicit sex thrills for me. But also there is the whole ass thing. Sadly, asses suffer from widespread discrimination. People who are happy to dress up their derrière  in sexy articles of clothing designed to attract widespread attention…would never think of  undressing that ass and actually taking it for a drive to see what it can do! Asses are often thought of as a dirty, nasty place that serves only one function, period. Well, let’s see…dirty? Absolutely. Which is why you wash it really, really well before you start playing with it!  Nasty? Yes! Nasty with a capital N and an exclamation mark. The juicy, titillating, throbbing, aching, fun kind of nasty. …Serves only one function? Well there are many many gay men who would beg to differ…and thankfully a growing number of straight men who have also discovered the joys of anal pleasure. *steps off soapbox*

Deliciously Dissident

Flouting  intolerant opinions is a hobby of mine. Above and beyond the ass itself, a lot people have judgments about pegging, from both sides of the dildo. If you are a man who likes pegging, clearly you must be gay…and if you are a woman who likes pegging, you wish you were a man. I love flying in the face of all those judgments and doing what I want just because I enjoy it. Sometimes I think that I gravitate towards kinkier stuff because there is a part of me that resists anyone telling me what I  should or shouldn’t do, most especially in the realm of sexual exploration. So if people view something as taboo – damn, that might be a hot thing to try! I am a bit of a rebel at heart. Does it give me a charge to know that if I told some of my friends about my proclivity for pegging, they would be shocked? Indeed it does. *smile*

The Visuals

The delectable vision of spreading those cheeks and sinking slowly into his ass…that is one of the hottest,  most amazingly arousing visuals I have ever seen….like, ever. Now I know why some of the kinkier dating sites that have amateur videos are overrun with clips of men holding a video camera pointing straight down as their cock is sinking into their woman who is on her hands and knees…I get it, guys! And from a different position, the look on his face when I am stroking my strap-on in and out…that surprised naked passion sort of OMG-what-the-fuck-are-you-doing-to-me-I-love-this look. It’s incomparable. His hands reaching back to pull his ass cheeks apart. Riding me and stroking his cock. So many visuals! Who says women aren’t as visual as men! If more women tried pegging perhaps the numbers would change.

My Pleasure

Do I get pleasure? Oh yes. Oh God, yes. Dripping throbbing, aching, clenching pleasure…without a doubt. I’m playing with how to orgasm while I am actually pegging my guy. Some women do…and I want to join them in that singular pleasure. There are dildos that offer a vibe in the base that are slated for experimentation…I’ll let you know how it goes. Might take a lot of practice…I don’t think he will mind.

Yes indeed, some women love pegging!.

Ruby Ryder