3/11/09
Confession: I Want to Do My Boyfriend with a Strap-On

Our contributor, a woman who wishes to remain anonymous, has a confession to make.

My boyfriend’s butt is beautiful. It’s pretty. It’s plump. It fits in the palm of my hand. I can’t keep my hands off it, and simply touching it turns me on. I’ve spanked it, kissed it, rubbed it, grabbed it, bit it — and now I want to stick something in it.  A strap-on dildo to be exact. I want to bend that boy over, face down, bum up, and do him in the most dirty of ways. I want to make his prostate gland giddy with anal afternoon delight.

So last November I said to him, “I want to do you in the butt with a strap-on. I think it’s only fair.” He’s not only put his peen in my vajayjay, he’s poked me in the tush too.

“Um, no.”  He laughed nervously and changed the subject. Needless to say, this no-bullshit approach did not work.

Unwavering in my attempt to stick my strap-on dildo where the sun don’t shine, I approached him again in December with a more sensitive strategy:  “Just because I want to pack your fudge and you let me doesn’t mean you are a fudge packer, baby.”  I thought assuring him I wouldn’t think he was gay, but rather a try-anything-sexual would work for sure. Sadly, this simply wasn’t the case.

“I know,” he replied, “I just don’t want a dick in my butt.  It’s not going to feel good.”

With this important information, I devised a more detailed put-it-in-the-pooper plan.  In January, sounding oh so scientific (and as cute as can be), I spouted off some knowledge gleaned from this very site:

“The prostate gland is similar in size and shape to a walnut. It is located at the base of the bladder and surrounds the ejaculatory ducts and urethra. It is essentially the equivalent of the female G-spot, hence it’s called the P-spot.  When stimulated during anal sex, it can produce orgasms. The P-spot is your best friend and you’re ignoring him. That’s not very nice, now is it?  From what I hear he is very fun to hang out with.  Perhaps you should make a play date.”

Silence…more silence…then finally, what my pretty little ears have always wanted to hear.  “Maybe…”

After a month of many talks about how to travel the brown brick road, we agreed that purchasing a vibrating anal plug would be the best way to get things started. February arrived and with it a text message from my boyfriend that read, “I’m really excited for you to do me in the butt. Wanna buy a butt plug today?”  Hell yes I do.  Butt plug today, strap-on tomorrow!

Last week we went to Fascinations, a local sex shop, and purchased our very first 4-inch blue butt plug.  We rushed home, stripped off our clothes and jumped into bed.  He looked a bit uneasy.

“Are you sure you want to do this?” I asked him. “I only want to do this if you’re comfortable with it.”

“It’s probably going to feel like a turd,” he laughed. Not the response I was hoping for, but he bent over, face down, bum up, just as I’d imagined, and after applying a little lube I eased that blue puppy in.

I started slow and soft, in and out, in and out, then applied a bit more pressure. After a few minutes I turned on the vibrator located inside the butt plug.  It was loud.  Very loud. The longer I sat there on my knees behind him, the more I felt like I should be wearing latex gloves and a lab coat; perhaps throw in a clipboard and stethoscope as well. Probing is the word that came to mind.  It felt far too formal for my liking, and I could tell by his silence and his face in the mirror behind our bed that he was not enjoying the ride.

“Okay,” I said. “Let’s try a different approach.” We sat for a few minutes and discussed what would feel good.  We agreed that foreplay first without the butt plug was a good idea.

Some plug-free fondling led to some plug-free fellatio. And when he was good and ready, I popped the plug back in. He liked this combination of front and back attention much better, as did I. But after a while my mouth and hands needed a break, so we resumed the prostate exploration in the spooning position. I inserted the butt plug half-way in and angled it up towards his belly button to start. “That feels really good. It’s vibrating my balls.”  Then I pushed the plug all the way in and started feeling around left to right.  “That doesn’t feel so good,” he said.  So I started making soft, slow circles inside.  He liked that a lot.

After about an hour our anal endeavor was over and the search for his prostate gland was called off.  He didn’t orgasm and he was strangely quiet as we lay there. It occurred to me that maybe I was asking too much. Maybe expecting amazing orgasms from just the push of a button was unrealistic. Maybe we should have thought of the plug as a side dish rather than the main course. Maybe P-spot stimulation just doesn’t work for some guys, just like some ladies hate having their G-spot touched…

Then he turned to me, smiling, and said, “Practice makes perfect, baby. I’m ready for round two.  What about you?”

Like I said, butt plug today, strap-on tomorrow.

Interested in Your Own Butt Plug?
The Top 5 Rules of Engagement for Backdoor Toys



588 Comments

  1. I love being dominated by the wife and she straps it on and fks me atleast twice a week. We have a large selection of toys in various types and sizes that we use on each other…….. That’s correct “each other”,
    The only rules we have are…… 1) boss/bitch. One day I’m the boss and next I’m the Bitch (sub/dom) and 2) the word “pain”, the boss can do whatever they want on there day and the Bitch got to take it and the only way to stop is shout pain….
    These rules work for us and we have an amazing sex life that we both enjoy and NO we don’t have sex every day but when we do we fully satisfy each others needs…….. Multiple times

  2. It makes me beyond excited, when I control his pleasure.Just getting started love to finger him,and make him orgasm, hope to soon work up to strap- on excited to know I am not alone. Took 20 years to feel this kind of pleasure omg wonderful.To many years afraid of what he might think if he knew how freaky I really was.

  3. emma…i wish u were my wife….ur sexual life with ur husband..is my dream..i hope i can get the same sex u described!!!

  4. Emma, I stand by you on this. It sounds like you are getting a lot of flack, but I, as a man think you are on the right track with this. You are the kind of woman men dream of. He is so lucky to have a woman that not only can be a breadwinner, but also give him the ultimate sexual pleasure a man can receive. There are countless men in marriages where they have to make the money and have unfulfilling sex with partners that just don’t understand that the way to a man’s heart is through his ass. I salute you, Emma.

  5. Had to add. He def screams and grunts and I’ll call it close to passes out after he rides me! I think, at least with him, he’s having no problem feeling blessed with pleasure! Any other gals who have male partners that don’t enjoy sex with a sexy lady? Or a guy if that’s what they like.

    Just sayin.

  6. I’ll admit I like pegging my boyfriend but because he grunts with pleasure! Thats a turn on! I don’t really care too much about a strapon as I’m proud of my body and happy with my own penetration by his maleness. I like being female and feel as much or more power, if that’s what you crave, be being the female and making his Big O as well as mine, so strong, he can’t wait to get home!

    Btw, we both shave. It’s cleaner and we feel each other more! Can’t say I find it tedious lol.

  7. Emma’s significant other needs to find a more loving home and discharge this abusive, self centered, possibly deranged partner. She’s definitely not a partner, nor most people’s idea of a sexy lover. By the words she’s chosen, I’m guessing not very attractive and hence her personality is undermined by anger and self dissapointment.

    Any individual of any gender that is selfish, finds enjoyment at the pain of others, carries anger and pride with degrading another is as far as you can get from attractive, desirable or normal. Being female, I’m dissapointed in Emma- if she is a female? Clearly she doesn’t speak for most of us.

    Hopefully he will wake up. Hopefully she will be stuck with a lover that turns the tables on her and she won’t remember her last orgasm but will remember the pain when her lover abuses her for their enjoyment. I’m guessing she’s not really into guys which is fine but even as a bifemale, I can’t imagine wanting this as a lover.

  8. Joe,

    Please feel free to regard my post as a “rouse”, or whatever makes you feel most comfortable. As far as I can tell it has no particular impact on me. But ruse or not I need to respond to these “sound scientific reasons”:

    1. My orgasms are inessential? Then I should be all the more thankful to the Goddess that I have been granted this joy!

    2. If you somehow couldn’t tell from the context, I was talking about pubic hair, where as far as I know we are more or less equal. And it has been a norm for women to shave there only in the last 25 years or so. So much for your law.

    3. I prefer to believe that he is proud because society prizes this attribute, and regards it as a proxy for his virility, rather than whatever pseudo-scientific reason you might concoct.

    4. I’m not sure what your point is here. If women
    control a resource which is scare and men one which is inexhaustible, would it not follow that women’s resource, and hence women, are the more valuable? Don’t men have to work hard to be appealing, and pretty, to women?

    And please don’t trouble yourself with my lot in life, I am quite content, but thank you for your concern. I will let you in on a little secret, Joe. A woman whose sexual potential has been maximized is able to experience pleasure far beyond what a man is able to, it’s not even close. Let me ask you, have you ever screamed because an orgasm was too intense? Cried? Convulsed? Blacked out? It really isn’t fair, to have to grimly carry out your biologically necessary role while we experience such bliss, apparently gifted to us by nature purely for its own sake. But that is your lot in life.

  9. Joe,

    Please feel free to regard my post as a “rouse”, or whatever makes you feel most comfortable. As far as I can tell it has no particular impact on me. But ruse or not I need to respond to these “sound scientific reasons”:

    1. My orgasms are inessential? Then I should be all the more thankful to the Goddess that I have been granted this joy!

    2. If you somehow couldn’t tell from the context, I was talking about pubic hair, where as far as I know we are more or less equal. And it has been a norm for women to shave there only in the last 25 years or so. So much for your law.

    3. I prefer to believe that he is proud because society prizes this attribute, and regards it as a proxy for his virility, rather than whatever pseudo-scientific reason you might concoct.

    4. I’m not sure what your point is here. If women
    control a resource which is scare and men one which is inexhaustible, would it not follow that women’s resource, and hence women, are the more valuable? Don’t men have to work hard to be appealing, and pretty, to women?

    And please don’t trouble yourself with my lot in life, I am quite content, but thank you for your concern. And

  10. To Emma:
    I don’t believe a word of your story. Your story is nothing more than a clever rouse that points out all the things you think are unfair to a women in a heterosexual relationship and than simply reverses that role.
    Look Emma, don’t let it get you down, there are sound scientific reasons why things are the way they are.
    1. Women don’t need to achive an orgasm to reproduce (although it does help), men must.
    2. Women are natural less hairy then men, therefor women shave what body hair they do have as a way of accentuating there femininity.
    3. A man with a big penis is a proud man, ask him why and he may not really know why, but the truth lies in our evolution, a big penis means getting sperm closer to the cervix, which in turn gaves a man a better chance to pass on his genes. And thick penis also helps the women orgasm, which in turn causes the cervix to open and close allowing for more sperm to make its way to the egg (most useful, but not necessary..Sorry Emma).
    4. Men have an inexhaustible amount of sperm they produce, so evolution dictated that men should never stop hunting for a place to put it, women on the other hand are born with all the eggs they will ever have, and thus the women was to be very choosey with whom she would reproduce with (plus choosing a good provider meant her offspring would have a better chance of survival), which also added to women trying to beautify themselves as a way to attract the best men possible.
    Look I could go on and on trying to make you understand why the human race works the way it does in hope you can feel better about your lot in life but I doubt a stranger off the Internet is going to do that for you, so good luck with your wishful thinking!!!

  11. @ Emma – You’re sadistic and controlling. I don’t care what your gender is. As a matter of fact, remove he and she entirely from your comments and it’s abundantly clear. I think whatever you do to your own body is just fine, but when you take it out on another, you’ve crossed a line. How would you like it if the roles were reversed? I enjoy pegging as well, but my lovers have always remained hard and orgasm multiple times. It is a role reversal and power exchange, but it’s not an excuse to punish them.

  12. I don’t intend to use this as a debate forum, but I would like to respond with a few remarks. Rather than mine representing a “bastardization of the women’s movement”, I feel that your comment indicates that that movement’s work is not yet complete. Feminism preaches equality between the sexes, but what does that mean? No one seriously proposes to mandate that every individual should be equal to every other. We live in a world of differences, and such a proposal is clearly unrealistic. Rather, I think it means that everyone should have an equal opportunity to express their potential to its fullest, including their sexual potential. Now, my particular sexuality finds fulfillment when I am in an unequal position with my partner. Men have been imposing this sort of inequality upon women, with or without their consent, for thousands of years. P, I take it you find this sort of relation offensive, and have expressed your moral outrage whenever and wherever you have come upon it? Or could it possibly be that your outrage was only aroused when, for once, a woman was on top?

    As for the particulars of your comment: In my view, yes, a woman penitrating a man with a strap-on does entail the assertion and yes the dominance of the woman. As it is my view, your idea of whether it “should” or not is irrelevant. And yes, using a large dildo is very exciting and ego-gratifying to me, ask a well endowed man and he will probably tell you the same. As to shaving, I think it is you who is out of touch with reality. You are right that some men shave and some women don’t, but you are very wrong if you think they aren’t very much in the minority. It is only women who are pressured and told that their hair, which I feel is beautiful, is dirty and repulsive. And I’m sorry if this offends you, but like I said I am the breadwinner and work in a very demanding and stressful job, and if there is something he can do sexually to relieve that stress and bolster my self-confidence (which is a matter of life and death at work), I think it is reasonable for me to expect that of him.

    1. So you view the act of typical heterosexual sex as an act of male dominance because there’s penetration? Then is it any surprise men view women as more submissive or that porn is a cesspool of unrealistically sized dicks “destroying” throats? It’s all ego related to size and what size can do.

  13. Emma,
    This is a great example of the bastardization of the women’s movement. For christ’s sake, sexual penetration should not be about dominating or self assertion. The size of your faux-cock shouldn’t be about emasculating your lover either. For you to say all of this and then make the claim about women having to shave being unfair because men don’t just shows that you are completely out of touch with reality. Many men shave and many women do not. In my opinion, everyone should be required to trim that mess back, but that is my opinion and preference and maybe that was merely your husbands preference as well. You sound like a very selfish lover. It is all about you and what you want. You are excited to have anal sex with him and cause him pain for your own pleasure with little regard for his but are unwilling to even shave to make going down on you more comfortable for him? Anal and oral sex, as well as any other, should be about all parties involved regardless of their sex or orientations, not just yours.

  14. Me and my husband have been doing this for some time now. The idea was always very appealing to me, and as I am the breadwinner and older than him by twelve years, and he is quite pretty, it seemed like a very natural development. I don’t really think of it as dominating him, but at the same time I do think of it as asserting my place in the relationship, and the psychological, ego-boosting aspect, especially since I started using a large (9.5″) dildo, is a significant part of the pleasure I receive. And I do receive a lot, I always orgasm at least once, and usually more than once. His pleasure is still a work in progress, I would love for him to be able to climax, but for the most part he enjoys it because I do so much. And this might sound terrible, but the fact that he undergoes pain for my enjoyment is very arousing to me.

    I’ve found that this has had huge benefits for our relationship outside of the sex itself. We are much less prone to argue, I feel that I am the natural leader of the two of us, and in the past he would feel compelled to challenge this position, just because he was male and he felt it was expected of him. This has largely stopped. And he has become a much better lover for me. I happen to love getting oral, its practically a necessity for me to function, and he used to be reluctant, especially when I would go without shaving, which I loathe (why do women have to but not men??). Now he actually anticipates when I need it, and is much more enthusiastic and committed to pleasing, and willing to continue until I am totally satisfied.

    1. Undergoing pain for someone’s pleasure is like equating the amount of pain they tolerate in a relationship with how much they love you, or you them. Kind of unhealthy thinking, and certainly egoic, and I find that desires like that are quotidian sadism, little disturbing aspects of our natures that are normalized. Why feel “cocky” about a plastic 9.5 in dick? You seem to equate dick size with power a lot (very phallocentric, societal thinking). Imagine a man saying the idea of his dick being so large it hurts a woman being intensely arousing (look at the popularity of brutal throatfucking or small teen big dick porn for a taste of this reality). It would seem disturbing, and it is. Or men finding penetration of a woman an assertion of their place in the relationship – making most relationships male-dominant.

      I enjoy using strap-ons, but I enjoy that the man isn’t tied up in societal gender roles and masculinity and doesn’t view being penetrated as an emasculating downgrade, not that he does.

    2. No wonder adopting something associated with female sexuality is seen as emasculating: it’s viewed as submissive, receptive, an ego boost for the man, a bit of a downgrade for her. This is why language like “they’re getting ass-fucked!” might be heard at a sports bar, exclaimed by a fan watching his team lose. It’s equated with submission, but pitching isn’t, sexual attitudes bleeding into colloquial speech, and alas, no wonder men don’t want to be feminine. It’s a raw deal to know your body and the penetration of your body is pretty much fated to be perceived as inferior, an act that props up the man’s ego, an act that’s inculcated lexicon to mean “destroyed” or dominated.

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