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

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563 Comments on "Confession: I Want to Do My Boyfriend with a Strap-On"

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Itsall Flesh Words
Itsall Flesh Words
1 month 20 days ago
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… Read more »
tom
tom
3 months 8 days ago
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… Read more »
Nikki
Nikki
3 months 8 days ago

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

tom
tom
3 months 10 days ago

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.

tom
tom
4 months 15 days ago

already had fingers and vibrators up into me felt good to be powerless

Touchthebooty
Touchthebooty
4 months 26 days ago

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!

Breelee
Breelee
7 months 4 days ago
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… Read more »
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