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Confession: I Want to Do My Boyfriend with a Strap-On

Wed, Mar 11, 2009

Confessions, Personal Post

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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 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.

 
 
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525 Responses to “Confession: I Want to Do My Boyfriend with a Strap-On”

  1. M Says:

    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!

  2. wb Says:

    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.

  3. bilbo baggins Says:

    Yeah..it means you’re gay…

  4. bill tattooist Says:

    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

  5. Twinkie Says:

    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!!!!

  6. Ambrosia Says:

    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!

  7. none gay dude Says:

    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 ……

  8. Milne Says:

    LOL, Bilbo Baggins! Leonard Nemoy sang a song about you. Now THAT’S gay! http://www.youtube.com/watch?v=AGF5ROpjRAU

  9. paull Says:

    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

  10. K Says:

    I want to try to my husband

  11. E Says:

    Pegging my fella is at the top of my list of favorite sexy time activities. He is very masculine and the level of vulnerability required to share pegging with each other has brought us even closer as a couple and more in love.

  12. Sublithium Says:

    A plug isn’t the greatest tool in the world for prostate massaging, and rarely do guys have an orgasm off prostate massage alone. My advice is to first get a toy designed for the job, there are many of them, and a hand will do just as well.

  13. andy meadows Says:

    its such a turn on – my thinking is that if women will take it there then men should – i have tried it a few times mostly it didnt work but it did once relax is the key

  14. D Says:

    Always do it with a finger first

  15. wishing Says:

    wishing I had a lady that would do that for me!!! lucky guy he is!!!

  16. Harry burton Says:

    I wish my woman would she would never think I would. But I would let her and the budget the better it not firsure but it sounds good HRB

  17. VivEk Jindal Says:

    Liked that post.. hope I will also find a life partner like that girl…

  18. LuckyMan Says:

    it’s amazing nad every guy should try it. My (female) partner gives me A and we are both very happy and very much in love because of our open approach

  19. Olivia Says:

    I can agree. It is only hot when the girl is into it.

  20. SlyServal Says:

    You should next ask him to dress up as a girl and wear a fake moustache!!!!

  21. Craig Says:

    I think that is awesome, would love a girl to do that to me, I have only experienced it alone, as the girls I have been with don’t seem to be into that sort of thing, but damn I wish they were, good for you all!!!

  22. J Says:

    My fiancĂ©e just recently did me with her dildo and it was amazing. I had done it by myself a few times but it’s no where near as good when u have someone do it for you.

  23. Larry Says:

    My girl friend had always wanted to fuck a man with a dildo, so after 5 years into this relationship I let her fuck me with a strap-on.
    At first it just made me sore. Then I had an orgasm as she was fucking me. She has fuck me with the strap-on maybe 6 times. She get real turn on my this and like to be in control.
    She like to finger fuck me more than use the strap-on for some reason, that ok. But if she going to fuck me I wish she would just not say anything and have the it on when I get into the bed. And tell me , “I’m doing the fucking tonight” I told her if she want to take control then do so. I told her anytime she want to be the one doing the fucking then just take it don’t ask. She was finger fuck me last month so I stop her and said, “get your strap-on and fuck me” She did and you should saw her face as she was in control. I told her that it would be hot if she would just have it on when I came to bed, then I would know what she wanted to be for the night. It would be so hot if she would sometime just take it from me, and give it to me good.
    But I always have to be the one to tell her.
    So I stopped saying anything and she stop taking it out of the box.

  24. hot Says:

    damn that is so hot the gay who have a women or a girlfriend who want to fuck him with a strap on is so fucking awesome i wish to meet a girl like that

  25. hot Says:

    how can make my girlfriend want to do me with a strapon


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