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. This article is shit. It only shows the limits of the authors imagination. Perpetuating the idea that ass sex is dirty or gay. You wouldn’t your man to think you think he is gay? Because being gay is a bad thing? Sexual turn ons to each their own, it’s not like people invent their notions, that is part of the fun, even if you did make up things, great.
    It /seems to be lost on women, plastic toys & condoms. The point for men is the physical sensation. Wouldn’t you want to climax from the reality of the moment. Instead of manufacturing a psychological ploy? Penetration is not automatically dominant. Getting fucked is getting. Your vagina, see how easy it is to say a word, vagina. Every woman has one. Your vagina takes a hold of a penis, that is assertive, figure out a way to assert yourself in way that is different from the boring macho stereotype.

  2. Doing a man anally is the perfect way to dominate him. You can start slowly by playing around his ass while you work his genitals eventually putting in a finger while he orgasms. He will associate anal stimulation with pleasure and being controlled physically. Over time start fingering him just for the sake of doing him without giving him an orgasm. increase the number of fingers you insert until he gets used to having his ass stretched and then introduce a dildo or vibrator. When he bends over on command and submits to penetration you will have achieved dominance. Your man will now be yours to hold and control and he will agree to almost any demand you make. Many cuckolds are created by this method.

  3. My boyfriend loves being done with a strap-on and I find it really empowering as a woman. It was a bit awkward the first time but becoming dominant was a really great experience and i recommend it to any couple that feels comfortable

  4. Not sure if I would enjoy being done with a strapon but I would love to have a woman who wanted to make me. When a woman does a man anally she becomes dominant and he submits and nothing is going to reverse things. I know lol.

  5. As a man who loves his wife and wants to keep her satisfied, if she wants me to surrender the booty, I’m more than happy to give it to her!

  6. My husband loves anal play and I’ve done him with a strap on. It was fun, but I’m a big girl too with a big belly so it was kind of difficult to position myself well, also I am definitely not built to slam it into someone. Afterwords I was just like, “I have no idea how you find the energy to plow me. That was hard. I’m exhausted!” he laughed and said, “Yeah but it was good.” (I’m a bit of a pillow princess, although I am hoping the Eva clit stimulator by Dame products will make riding my hubby far more orgasmic someday!)

    Anywho, as far as anal play on het men goes, well people shouldn’t be so uptight about this. Just have fun, enjoy each other. My hubby is still 100% heterosexual after the fact and definitely still a chubby chaser too~ <3

    Still, if you don't want it in your butt and that's where you draw the line you have every right to say no and she should respect that. =)

      1. These days, designed is a more apt description of people. Regardless, if a woman were meant to penetrate, she would arrive in the world equipped with apparatus capable of developing to do so. What is a clit if not a half baked penis?

        1. She does arrive in the world equipped with appendages capable of penetration – ten of them. Fingers. More if you count toes, but let’s not.

  7. Being penetrated as a man in the bedroom is not only completely changing the dynamic of your relationship, but compromising your sexual identity as a man. Some guys may be comfortable with that. Real men aren’t.

    1. Michael, how exactly does receiving anal attention from your girlfriend/wife “completely change the dynamic of your relationship”? You are both just enjoying pleasurable sexual sensations together. If both parties are having fun in a new way, then the dynamic is simply being improved upon! The only way your comment makes sense is if you perceive heterosexual intercourse as something aggressive that all-powerful men do to receptive, submissive, less powerful women — and thus being penetrated by a woman would make you some sort of “gayish girly-man,” giving her the power in the relationship and stripping you of all of yours. Which all sounds incredibly sexist, homophobic and myopic to us. “Real men” are people whose sexual identities aren’t precariously based on sexism, homophobia and old-fashioned ideas about gender stereotypes — they are people smart enough to understand that some nerve-endings feel good when they are stimulated by a partner they’re attracted to, people who are willing to be vulnerable with those they love, and people who don’t resort to knee-jerk name-calling when others behave in ways they don’t like or understand. In other words: phooey on you!

      1. you perceive heterosexual intercourse as something aggressive that all-powerful men do to receptive, submissive, less powerful women — and thus being penetrated by a woman would make you some sort of “gayish girly-man,” 

        ^ This is all good and well, but you make comments about penetration an act of dominance, so it does sound like most sex, as most sex is heterosexual, is an act of male power done to receptive women who are as a result less dominant and powerful during. At least be consistent. If female sexuality is usually submissive, women may never be fully seen as “equals,” as there are likely psychological effects to associating a body with submission. Men look more powerful, have a more active sexual role that’s perceived as dominating – ruling, controlling – while the woman receives, looks at his mercy when penetrated. We don’t win here.

        1. I am a very tough guy and when I was young I did not realize how strong and tough women can be. I know that some women can whip my ass and have their way with me and it has nothing to do with size or muscles

    2. Bwahahawhhw “Some guys may be comfortable with that. Real men aren’t.”
      Yeah. Some guys are uncomfortale at being gay, but real men aren’t.
      Ridiculous denial at it’s very best.
      Wanna be buttfucked? HELL, DO IT! You’re paying your own bills, aren’t you? Damn, so what?
      Wanna live in denial of actions not to threaten your sense of Self/Person whom you think you are? Hell, DO IT TOO! Again, no one should really have authority to stop you there too.

      Problem is not raping your asshole, it’s being an asshole who rapes reality.
      “Be a man” to accept who you are and fitting your Self with your actions. (that’s a wonderful invitation to distort and fuck reality over again, innit.) Or not. You don’t have to, right.

    3. A real man will never let a woman or another man bend him over and do him in his ass ,hell fuck no!!if you let anyone do that to you and you enjoy it ,you are gay in denial.
      I will never respect a man that let’s a woman or another man do it to them in their butt no way.

    4. I let my wife do what she wants, its not gay, that’s just how indoctrination. Its actually really fine.
      I don’t believe in gay rights before you accuse me of being some super gay promoting weirdo.
      I like a dildo or a strap-on up there because I’m absolutely comfortable with myself, and my wife a comfortable with herself.
      If it feels good, do it, is our rule.

      1. Um, nobody is going to accuse you of being “some super gay promoting weirdo,” because no such creature exists.

        It’s kind of ironic that you enjoy receiving strap-on sex with your wife, i.e. you’re two consenting adults who care for each other and want to pleasure each other in ways you both enjoy in the privacy of your own home, but you “don’t believe in gay rights,” while there are plenty of homophobes who’d be happy to outlaw what you and your wife are doing.

  8. The ultimate in female fantasies, rape the male and take away his masculinity, now Feminism is the power, not equal but more powerful. Women around the world orgasm in delight.

    1. That’s not the ultimate “FEMALE” fantasy. If you’re near a chick who’s faintly into not accepting/reinforcing your masculinity/her femininity, DROP HER, TEAT HER LIKE THE PLAGUE.
      If you have no idea, according to most researchers, it’s actually to BE raped (as a FANTASY, not the real thing).

  9. It was weird getting turned on while laughing readind this. Wouldn’t mind having someone to do me.

  10. Man… I so want to do my husband with the strapon but he keeps saying no… It’s been a couple of months since I started pretty much begging him to let me do it to him 🙁 it’s my biggest fantasy and turn on right now but I have a feeling it will never happen 🙁

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