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. MOST straight man are curious to try it,but its so hard for us to say(“babe suck my dick and finger my ass”).mostly coz we fear you might think we gay and how embarrassing its going to be if you say no..
    LADIES:start it easily with ass licking on blow jobs section,just make it feel natural that you not thinking its an manly but rather you enjoying it..from ass fingers to little dildos all the way to strap on we go there if we feel you dont think we not straight.

  2. Me and my partner bought a strap on last year and so far it has just stayed under the bed! Im determined to use it but hes panicking about being clean. We have an honest relationship and he can talk to me about anything but this is a real sticking point, ive tried telling him that any ‘accidents’ that do happen can be easily ignored but he still wont. We have lots of dildo’s and vibrators to use but he wont even let me use a finger 🙁

    I just want to make him happy x

  3. Ive been with my husband for nearly 20 years. We’ve always had a good sex life, trying new things. He’s been having anal with me for years & occasionally asked me to pop a finger in him. He recently ordered some new toys & I was shocked to see a strapless strapon amongst them!!! Well it was a massive turn on to wear it & we both had some of the best sex ever. I am looking forward to continuing our anal adventures… 😉

  4. Riley,
    You should try writing him an erotic story about the two of you and include playing with his ass. I did this for my wife and as of now she will rub my anus during oral and intercourse. Wrote her another story and now she seems open to the idea of putting her finger in. Little steps…Until I can get her to use toys, then a strap-on, wish me luck as I wish to you!!

  5. Im a very open straight girl and when my bf FINALLY admitted that he liked his butt played with I jumped on it. I love to be dominant! And he just took it in stride. We got a strap on and I fucked him like crazy but before that we just would use toys and explored different things.
    My boyfriend is straight and not even bi-curious lol and what’s funnier is he is a rough and tough country boy cage fighter.
    This article makes me feel a lot better, kinda thought this was something weird that no one else really did! Glad we aren’t alone!
    I love fucking my boyfriend and he loves being fucked.
    I think it makes sex that much better when you can both trade off back and forth

  6. Ok so I *love* doing this to my boyfriend. He is so pretty and so, well, receptive, it’s just wonderful. Its a major power trip for me, especially since I use a very large dildo, I love the way I look wearing it, and I’m so much bigger than he is 😛 Luckily with the strap-on I use the center of the base naturally rests squarely on my clit, it really feels like a clit extension, and I usually have multiple, quality Os in a single session.

  7. Ive had two dreams with impailment. One where a hot chick whos one of ny friends was impailing my behind with a giant strap-on dildo. And abother where two of my buddies were getting the same from there gfs and me and mine were like huh so thats tge bew thing nowadays huh, and i once again got impailed in the bottom, and enjoyed it.

  8. Hey that’s badass that so many of y’all like it, I love it up the ass
    By a woman, my girlfriend really likes it and loves to make me wear her panties and all that stuff.
    I have never been attracted to men but there is something very sexy about a woman taking you in the bedroom every now and then.
    So I love it and I think it’s cool to see so many woman into it, because when I first started liking that people I asked was like that’s gay but I didn’t care haha I’m 22 and I was 17 when I started playing with my ass but ya anyone and everyone do what you do and don’t care about what other people think

  9. I would love for my wife to want to include anal play in our sex life, but she does not seem too interested. I am not attracted to men,but I sure like my Butt played with. And I would let her insert a strap on. but it needs to turn her on, too. We have good sex and she is ok with me masturbating, which I love, but the anal on me part would increase my pleasure levels.

  10. I always wanted my wife to try it on me but she will not even talk about it. I’ve pretty much given up on the idea but find myself fantasizing about a women with a strapon.

  11. Iv always wanted to do this with my husband he lets me use my finger sometimes but only because i like it haha I’m interested in using a dildo or something on him, but I’m waaay to scared to ask him, if i get rejected asking him to do something that i fantasize about …i think i would die or embarrassment! Even though he’s my husband i still have those fears or him thinking “oh shit i married a freak” he probably won’t but im still scared of the possible rejection. What are some other ways i can possibly get him into it??

  12. I want so badly to have my wife take my ass with a strap-on. She’s great about giving me analingus and fingering . . . ooh! But no toys. I have to use them on myself when she’s not around. I’m working on her, though. Please baby, please!

    This straight man desperately wants a woman to make him her bitch.

  13. dudemon 100: NEVER, EVER use someone else’s sex toy without their knowledge and consent, ESPECIALLY if you are using it anally. That is not only a drastic invasion of trust and privacy (and yes, there is and needs to be privacy in intimate relationships, even marriage), but cross-contamination of bacteria, fluids, etc… can lead to some TERRIBLE health repercussions. Women are advised even to have their own separate dildos for anal/vaginal use, and that’s without bringing a foreign body into it. I hope you haven’t ever used another partner’s sex toy like that again. Don’t do it. Ever.

Comments are closed.