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. I have an office job and my wife is a stay at home Mom. She has ben working out at a gym for a couple of years and is muscular and fit. She is a lot stronger than me and introduced me to strap on sex one night while the kids were away. She surprised me in the living room wesring nothing but her toy around her waist. She pulled me off the couch and hoisted me across her shoulders. Carried to the bedroom she threw me on the bed and ever since that night she has dominated me and I love it. The combination of muscles and strap on always lead to fantastic sex.

  2. My wife has used toys on me before and I don’t think I have ever been so turned on in my life. But now I want here to do me witha strap on and I don’t know how to tell her. She was very uptight about sex when we first started dating but has been more and more open about things as time has progressed but I just don’t know how she will react.

  3. To lunar lindle,

    You are a judgmental whore, go fuck yourself because the male prostate is located in the ass and the most powerful orgasms come from stimulation! You are a loser! I am a straight male model with a smoking hot girlfriend who fucks my ass!

  4. Are you serious? I have had 5 different girls do this to me! I mean at first you think its gay but then you realize, this is with a girl! Not a guy nothin gay about having nasty sex with a woman.what ever your doing

  5. I tried it for the first time today. WOW. Guess my eyes were bigger than my a*s*o*l* because it took a long time to get that rascal up there. My toy was a 9″ latex dildo with a suction cup. After about 30 minutes I finally relaxed enough to allow it to fully penetrate me. I pushed the suction cup onto a chair and did squats on that rubber dick. Oh lord just thinking about the reverberating waves of pleasure that I didn’t even know I could ever feel, pulsating into my rockhard cock is giving me a woodrow that a cat couldn’t scratch.

    For a while I did my squats, loving the ‘full’ feeling. My penis was so engorged with blood I thought I might explode at one point. At last I did some deep breathing and allowed my self to take it to the base. I sat down, nay I was impaled on that rubber dick. I’ve never experience anything like that in my whole life. I just sighed and moaned for about 5 minutes…just waves of bliss. WOW!

    My legs started to get tired so I concentrated on reaching orgasm. It seemed I might be able to cum without touching myself at times but I ended up stroking my cock while grinding against the chair. I don’t think I’ll ever be the same again! 🙂

    So now I’m thinking I don’t want to do this too often. Like I’ll reserve it for special occasions. I don’t think my anus can handle that regularly. As it is I’m thinking it’ll take a few days for my ass to come back together. 🙂

    BTW, to the original poster. Wonderful, well written, humorous confession. I’m glad I googled “Why does getting fucked in the ass feel so good” today. 🙂

  6. After some discussion and some finger-pokery i let my other half use her viberator on me, hit the spot boom. I then told her the thought of femdom, dress up, tie me down and use me was something i had thought about and turned me on. She was reluctant in responding but when she did it wasnt the niave response of well maybe i was expecting.. 🙂 few days later i came in the bedroom to find candles all over her in full femdom gear and a nice flesh-like strap on, she got my length too so “i know what its like” after alot of lube later the baby was in, i was tied down and it was the most intimate night weve ever had… To let someone “poke your poo” as ive heard it expressed, throw all taboo out the window and just relinquish all control to the one you love… For me thats just what i want.

    For those who are new to it, relax.. No really relax nothings fitting up there otherwise! Read around, play around and ultimatly do what you feel safe with. Most important above anything is lube! Sometimes more is better but dont be stupid you dont want that flying in. ( i assure you, it hurts)

  7. I have recently got together with an old flame that was always into stuff, he told me that he really likes to be stuffed up the ass with fingers but has never been stuffed with a dildo….so guess what i have bought a strap on to give him the delight he has waited over 15 years for me to give him… turns me on just thinking bout it so we is gonna have one hell of a night. our motto has always been.. try things once if you don`t like don`t do again but at least you tried. I have and never looked back.

  8. My girlfriend finally talked me into it. I ended up loving it..and can’t wait till the next time she does me in the butt..its the best orgasm ever

  9. I was introduced to this by two women I didn’t like it to much untill they were done with me. I’m not gay. I’m not bi. But there is nuthing like being over stuffed with her baingingmy ass. It fells so good.

  10. I hit the wrong button. Well after assuring her I was straight often she’s just convinced that this all I think about and she can not or is not able to give me what I want. Can’t discuss it anymore. Talk about screwing yourself…. We just can’t make people what We want if their heart isn’t into it. That’s my little story. Patience and make sure you listen to everything said because women will tell you everything. Sometimes too subtly if you get too anxious. Hope that made sense.

  11. A word or note. We done it and not everytime was great. But I would say anything bad, well I’ve always fantasized about femdom. She was so accommodating. We had a blast.pulled off the whole fantasy in spite of unwanted suggestions or requests from me. My point is be patient with something you really want especially with a partner that never thought or dreamed about strapon. She was offset by how often I talked about wanting to play that she thought I was gay. At least bi curious. Trust me im not. There is nothing uglier than a mans ass. To me. But ladies in black or tall boots!! Anyway I talked myself out a future of occasional fun with toys. We hardly touch at all becauseafter

  12. For lunar lindle,
    That input was entirely useless, so let me be the first to thank you for sharing complete incompetence. Go back to playing in the sandbox and let the adults talk.

    To OP:
    Congrats on being able to share that. I never thought about any of this untill last night that I was with my girl and i was under the influence of herbal goodness. Now that I read your confession, I may just be able to talk her into it lol.

    Side Note:
    If you’re a guy and reading this and your first thought is “Put something in my ass? fuck that thats for fags.” I would implore you reconsider your knee jerk reaction to what you have been forced to think. Its an insecurity. If you hace tried it and have found it uncomfortable, well then its just not your cup of tea and thats perfectly fine. But if you have not tried it and react with ” You’re a queer if you do.”, it proves that you are a bit insecure and rather close minded. Try it, it may make your sex life with your partner amazing.

  13. Lol.

    Your boyfriend is a queer.

    You are sick and insecure.

    You both lack any real intelligence.

  14. I can tell you that, from experience, being pegged by your woman can be an unbelievable experience. My wife and I have tried it several times, with a glass dildo, a vibrating butt plug and a strap-on. Practice does indeed make perfect, but once you get the practice down, the experience is unreal. We actually did this last night (with the vibrating butt plug) while my wife blew me, and it was the most intense orgasm I’ve ever gotten from oral.

  15. After being married for 6 months, my husband randomly told me his fantasy of being screwed with a strap-on. It wasn’t something I ever put thought into, so I wasn’t necessarily turned on or off by the idea. Now that he tells me about the things he wants me to do to him, I instantly get turned on by the idea. We’ve been doing anal on me for a while, but now it’s going to be a mutual thing.

    Men shouldn’t be so afraid of this and women shouldn’t be so turned off by it. In my honest opinion, it’s as intimate as you can get. If you can’t share that with your spouse, what CAN you share? :/

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