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 never wanted anal sex play of any kind. I tried it in my early years and it did nothing for me. When I was married, my wife wanted me to penetrate her back passage. I did this once but neither of us enjoyed it.

    Any woman who asked to penetrate me with anything would receive a polite No. It just does nothing for me and I speak as one who has engaged in many different sexual acts and with multiple people and MMF and so on.

    Mutual respect for boundaries and what pleases are the basics.

  2. i think every guy should try it… my man asked me one day… he was realy shy… he said 9 in a laughing tone but i knew he was going somewhere with it) .. maybe we should get a strap-on… at first i was a bit unconfortable..but more i thought of it more i was getting exited…!! Now we use it all the time!! i love it.. he loves it.. and we are willing to go much further… i dont think any of this is gay i think its more Trips you want to try!!..

  3. Jason – it sounds like I am on the opposite side of your situation. My husband has given me hints that he would like me to use a strap-on on him (I did go so far as to purchase one, but we have never used it). My first problem with it is the fear that if I do it once, he will want it every time, which leads me to my second problem – what I fantasize about is a man dominating ME in the bedroom. I suppose in an ideal world, we would openly talk about this and arrange some sort of trade-off (I do you tonight; you do me tomorrow, etc.), but so far I have been unable to share my fantasies with him.

  4. i really want to do it with my boyfriend..he always make me piss off..but i love him so much..i want to fuck him…damn!!!

  5. I have been married since 2001. I am very kinky. I have always wanted my wife to assume the dominate role/role reversal in the bedroom. I have even purchased a strap on and anal toys and have asked her to try them out on me. She has only used the strap on twice and only after much insistence. I am not gay or bisexual. I just love a dominate woman in the bedroom. I don’t know how to get her to do this. I have hinted around it for years, then last month I finally got so frustrated that I told her straight out. She still hasn’t gotten the message. Can anyone help me out? I don’t know how to get her to step out of the straight sex routine and live on the kinky side for a while. Im very nice looking. I have women hit on me all the time. I have never cheated on my wife and I do every thing i can to make sure my wife’s needs are taken care of, but I can’t get any relief myself and its very frustrating. I need some ideas to get my wife out of her shell. I don’t want to live in fantasy land and jerk off forever.

  6. I agree Lucky Lady…Sounds perved to me. Sorry. He needs to choose which road he wants to be on..He is the selfish one.

  7. So glad to find this forum. My ALPHA male bodybuilder boyfriend shocked me when he told me his biggest fantasy was to wear some stringy panties be dominated with a strap on. I’m very open minded sexually, but felt a little uncomfortable at first. Imagine a 285lb muscle man in thong underwear, face down, ass up… waiting for little slender 5’10, 130lb me to give it to him with a 8in black dong… Lets just say I was pretty nervous and decided a few vodka sodas were needed the first time we tried this… and … it really wasn’t that bad.
    Now fast forward 8 months later… We probably use a strap on once a week or so, me on him, him on me, sometimes with just our hands, sometimes in a harness. We talk dirty to each other about being dominated.. he pretends to make me give him a blow job… and I might handcuff him in bed and sit on his face.. We spank each other.. we tease each other… He wears his man panties one night to dinner.. I might forget to wear mine another… ECT.

    Nothing wrong with any of this if you ask me. Im glad we can talk about our fantasies together and act out some. For those who are afraid of the whole idea… just keep talking about a it and be sensitive to each others feelings as well as sexual desires.

    good luck!

  8. Help me i have got all the does but she is not keen just yet…. i will wait for her to make her mind up when.. but how can i make it sound keen to her?

  9. F.Y.I.
    Any sex act between a man and a woman is not gay.
    It’s only gay if both people are of the same gender.

  10. She plows me all the time i love it. She is so cute when she puts the leather on starts whiping me and just butts the 11 inch all the way in wish we thought of it sooner

  11. ^Ah jeez… Do you know how many guys out there would do anything for a girl who actually wants it in the butt?

    You should get a kinkier boyfriend, that’s what.

  12. my boyfriend has a gorgeous perky ass and i always fascinate about giving him a rim job or fucking him with a strap on but he absolutly will not do anything involving anal
    he won’t even anal me and its my biggest turn on. what should i do?

  13. A quick recommendation for gentlemen interested in receiving some backdoor action from their ladies- start slowly. Buying her a strap on, lube and arranging yourself on a towel as a welcome home from work present will most likely result in her being damned uncomfortable. I love giving it to my man, but we also eased into it, using smaller, handheld prostate massagers at the same time as oral sex, experimenting with each other and focusing on the pleasure. Let her know that you think it’ll feel amazing, and that that is an experience you want to share with her. If she cares, she’ll be interested at least in making you feel good. Have her take the initiative- buy a toy or two and (Good quality) lube, put them somewhere discreet, and make sure she knows about them. Give her a chance to get used to the idea. Wait a bit to see if she brings them out, and if not then introduce them during during foreplay and watch her for reactions. Patience is key! If she’s into some power play dynamics, why not cuff yourself together and give her your body? Anyways, good luck and great pegging.

    T

  14. I’ve used a strap on with a few guys. It’s best to buy the most expensive, as the cheaper ones don’t have the best harness, and that, for good fucking, is essential. The shape of us girls don’t fit a strap on too well, and we need the harness to be strong and tight. If the cock is not moving with your hips, then you’re expending a lot of energy for nothing.

    I’ve a bi friend and he frequently wants to fucked with a strap on. He likes it when he’s on all fours sucking a guy and I’m giving it to him from the back. Of course, a lot of men don’t go for a strap on experience, some only want to fuck us girls in the ass and not reciprocate. But some guys once they’ve tried, felt all the sensations attached to using a strap on, really like it. Some have told me it makes their orgasms really incredible.

    I’ve also used a strap on on several women, girls quite often like it.

  15. I’ve recently been introduced to strap-on play with my boyfriend… he’s absolutely LOVES it, which I didn’t 100% expect. BUT, the biggest surprise is how much I enjoy it…

    It gives you a sense of power.. Role reversal is an amazing thing and can be transforming.

    I found this website for strap-on lovers. It’s like a social network for people just like us!!

    It’s http://www.SocialPegging.com/

    100% FREE so try it out. 🙂

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