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. you sound like my wife!! i can tell that you and your man are going to b every happy for along time!! myShe does me as often as i do her!! LOVE IT!! PAULL

  2. If you do a sex act with a dude you are gay or bisexual …if you do a sex act with a chick you are strait or bisexual …..its doesn’t matter what the sex act is ….anal play feels good and its fun to give the girl a little controll every once in a while ……

  3. Thanks for the story Emma! My boyfriend and I have been talking about doing it so I’m doing my research. Like Emma, I love his butt and looking forward to it. It doesn’t mean he’s gay, it just means he’s into exploring new things with someone he trusts…get over yourself Bilbo!

  4. Yay! My hubs and I are HUGE fans of “pegging”! This fantastic experience is a regular practice in our house. My husband is far from being a closet homosexual. I think if you asked, most men would at least be open to anal play. It feels great to them, and what a rush for us gals! I say, hooray for the peggers!!!!

  5. bilbo baggins chose the name bilbo baggins an calls someone gay lol, not to be mean, just be open, im straight as it comes an finally caved to doing it, id beg for it now as well as many other things as long as its me an my gal only

  6. Ohhhhh….man.
    After 30 years of marriage, i was fortunate enough to have my misses pull my “a” card and WOW.
    Now its at least 3 or 4 times a month.
    She has multiple orgasms and i have an orgasm like never before, not to mention my prostate problems and discomfort has DISAPEARED.
    It doesnt mean your gay, it means you enjoy the power exchange with someone you love and you enjoy sex like nothing you have ever experienced.

  7. Emma sounds amazing. Her man sounds like he is happy or he would have left her long ago. An unhappy man is hard to live with and an unhappy sexually frustrated man is worse! Everyone stop judging Emma and her man. They sound happy and content!

    Why is OK for men to dominate women but when a woman shows a bit control she needs to be put on a leash?! All you sexist pigs disgust me!

  8. I agree with Emma. I’m a male though, but I like to funk a girl in the butt, and I feel more dominant when I hear her squealing. I guess she can’t have an orgasm that way, but it gives a great pleasure to me. Pure sadism.

  9. i just wanna say that i see nothing wrong with emma pegging her man however i disagree with the method as sex should always be a mutually pleasurable expereince and if he isnt “getting off” then neither should you. If the roles were reversed the same would apply. feminism and masculinity has nothing to do with it. its merely the right thing to do

  10. Some of these comments had me rolling! Are you people for real? My ex was a big scary man & the things we did in the bedroom didn’t make him less of a man! He loved his ass played with in many ways, loved to be called dirty n mean names, talked to like he was worthless, loved being slapped, and chocked! He never did these things to me “well accept butt play ” I wasn’t into it, that was all him! I felt strange at 1st doing it “but” sometimes we do things for the one we love to give them pleasure!

  11. I have had the fantasy of using a strap-on for a long time now. I have reunited with a lover from the past and he has the same fantasy as I do. Turns out he has been anally pleasuring himself for most of his life. Now we are looking to get a strap-on so I can do him like he does me!

  12. My wife and I loved role reversal for a while. It’s fun. It’s different. It feels good, trust me. We haven’t done it in a while for a number of reasons but I still enjoy it. In fact, I often walk around with a butt plug or even a dildo in just for the sensation and the thrill of it. I am not gay. Just enjoy exploring every aspect of my sexuality, which I believe is healthy. A complete person is not male or female, but a little of both.

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