Asking Her to Try it

Podcast #112 For the Ladies

A podcast recorded specifically for the givers that addresses their fears and misconceptions. Please listen to it alone before you listen to it with your partner, because only you can decide whether it's right for your situation.

Most of the time it is the men who want to convince their woman to peg them. This article is for you gentlemen. If you are a woman who wants to take your man's ass and he needs convincing, click HERE for your article.

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 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 all, period, end of discussion, case closed. But let us remain hopeful...



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.

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. read an article about prostate stimulation 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. 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 open to receiving 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 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 is much easier to introduce the concept of her exploring your ass. (If she refuses - see below "Last Ditch Effort".)

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.


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 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. In fact, it's best to start gradually with ass play instead of jumping right into pegging. 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 "Keep it Clean, People" and take the advised steps to ensure a positive experience for both of you.

Don't 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!

Last Ditch Effort

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

Since writing this I have received a comment that I consider important to share, as it touches upon an important point not covered in my article. Thanks to the reader who contributed this different point of view - you know who you are!:

Your page about convincing her is very good, but missing a VERY important element: time.

The time I'm talking about is the wife's time to be available or interested. Many wives with children and maybe a job are so overworked and over-stressed that the only reason they have any sex with their husband is, it's one more task they feel is required in a marriage.

Many husbands figure that since they work long hours and bring home most of the money, they can leave the household and kid tasks to their wives. That leaves the wife feeling like an unpaid worker, a slave. Not the best mental attitude for sex.

The husband has to "liberate" his wife. That means taking on 50% of the household and kid work, without being asked. Once the wife realizes that she has a real partner who understands her, everything is negotiable, even sex acts.


7 Responses

  1. Brilliant article. And, once again, thanks!

    We went the prostate stimulation route. Finger to silicone plug to Aneros to harness & dildo. The biggest hurdle? Getting her to agree to buying a harness. Once the harness arrived, it couldn’t just go to waste… and she was instantly hooked on the first time out.

    For the men who want to do their ladies… Wife has become openly curious about receiving anal sex after watching me collapse in a heap on more than one occasion. I’m actually pegging her now, with a really small dildo. Working our way up slowly.

    1. You are so welcome. I love success stories…

      (Smile) And how would that last part work? You pegging her? Thanks for the heads up on this sweet and reasonably priced little piece of equipment that readers might be interested in. DP Harness. I’m quite sure there is a reader out the who’s been looking for something exactly like this!

  2. My situation was somewhat simpler … She told me that she was not interested in anal play yet. She told me it was something that she was saving, although I think honestly it was mostly nervousness.

    Eventually I had her tied up and turned on enough that she let me slip a finger in and after she’d had the intense orgasms associated with anal and clitoral/vaginal play she was fairly sold.

    From there I suggested that we get her a toy … and she insisted that if I was going to try it on her, she would get to do the same for me.

    This was a couple of years ago. Now we are about to try our second strap on: the doc johnson ultra harness 2000 and she is getting so excited. Unfortunately we weren’t very sold on the feeldoe which is what we’d tried previously … Too rigid (because it has to be) and not enough pleasure for the wearer.

  3. Hi one way I have found to see if a woman is in to having her bum played with is to have her in top facing your feet when licking her. So get started as normal licking her , not to much clit to start with. Work around and start to stray towards her bum hole a little at a time just for a few licks and then back towards her clit .
    Because she is on top and can roll her hips ,in most cases you will find if not the first time you do this that you seem to .
    a) be in this her on top position at her instigation but ,
    b) she moves her hips so that at least some of the time she makes sure her bum hole is very available for your tongue. It is then your duty to oblige her and then as you lick around her ass it will open up like a rose in the warm sun . As the good lover you are spend as long as she wants you to lick as deeply as you can and a lot of woman find this very pleasurable before she will then move her clit to your tounge to bring her to orgasm xx

  4. Thanks for the comment! This sounds fun….BUT…you need to be aware of the do’s and dont’s here…

    Licking back and forth from ass to clit or ass to vagina can easily give her an infection. Asses have bacteria that need to be taken seriously. It is good to use one hand for ass and the other for vagina or clit, for instance. It is not good to go back and forth, whether with hand or tongue.

    I can absolutely see playing with her ass with a finger, though….or giving her lots of attention with your tongue on her clit for a long time and then switching to her ass…

  5. Foreplay needs discussed more. My girl fingers my ass for at least 20 minutes lubing and stretching me. She has small hands, so is able to fist me, and really get me ready to take her dildo. I must say that taking her cock in me is the most stimulating thing we do.

    1. Everyone’s foreplay needs are pretty individual in terms of what they like done to them, but I do emphasize over and over to take things slow. In my writings, webinars and advice I am always talking about taking it slow and waiting until your receiver is asking for more or backing up into you. Plus, there’s this:

      Yay for you and your lady (and her small hands)!

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