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.
wow,i wish i could find a woman like you,I just love butt plugs and dildos
holly it seems to your boy friend dose not want it but if you tell him what the prostat glans can do he would more then likely let you you got to read up on it and you well know what to do if you lived close to me i would let you do my butt all day i’m not bisexwal dut i do enjoy leting wemen have my butt if i can put my penus in them i can let a women put there strapon in me i do enjoy puting my butt in the air and let a women hite it i like it it fells veregood to me and it gives me anul orgasums.
I asked the girlfriend to do this for me, and out of love she did. At first she was at unease thinking that I might be gay or somesuch. It was relatively early on in the relationship and we were only begenning to explore our sexuality. I explained that I’d messed around back there with a toy that I’d bought and realised that it felt damn fantastic. I openly admitted I also like to be physically dominated by her (or rather had fantasies of such). I took a risk in telling her this, and doing so definitely brought about a weird vibe between us for a while. However, we already had a good degree of trust established between us, and only for that it certainly could have ended there.
She decided to give me what I wanted, and the first time it was a disaster with a horrible smell. Second time it was uncomfortable and I got annoyed that I was not getting any satisfaction from it. Third time we were drunk, she got in to the swing of it, and when she could see the fun I was having, she began to loosen up about the whole thing. It took patience on her part as well as mine to get the art to it.
She did not get off on the idea nor the physical sensation for the first few times.
It was only when we did invest in a proper strapon + dildo + bullet viabrator that she could begin to get some good physical sensation from it. She did admit though she quickly likened to being the dominant partner sometimes and that it got her aroused in ways never experienced before.
A year and a few months on from that we often look back and laugh at how naive we were about it all.
It doesn’t seem like that big of a deal anymore.
If you’re a guy reading this and wondering whether to let your girlfriend try this on you… I’d recommend reading up on the prostate and playing with it yourself. The only thing left stopping you now are probably insecurities and homophobia, and if so, they are the cause of you missing out on a hole load of phun.
If you’re a girl reading this wondering what the is wrong with your boyfriend… I ask, what is wrong with you?
Oh, and Jessica, you are not in any way selfish, and he is an insensitive asshole to even contemplate getting a “friend” to help him get off if you are having trouble understanding. If he honestly feels like that is a solution, rather than communicating with you and working things out, or fuck, sacrificing his desire for his love for you, then he is not worth your time. Been there, done that, sister, and that is a shitty thing to do to someone you supposedly care about.
I know that I am the most privileged woman in the universe, but my husband LOVES me to play with his ass. He has and never will be bi, but he loves how it feels, and both of us are very open to new experiences in our sexual life. We have touched and tasted every single part of each other, and when I say “every” I mean EVERY. I was not very keen on the idea of playing with my boyfriend’s, now husband’s, ass, but knowing how much pleasure it gives him, and how grateful he is that I love him enough to try, makes it much easier and infinitely more pleasurable for me. If you really love your man, then talk to him about how it makes you feel to think of doing him like that, and let him tell you why he wants it and why he thinks it would be pleasurable. And one more thing, I know it sounds funny, but try doing it by yourself. Grab a pillow, fold it in half, and go to town. Imagine yourself as the dominant party, giving it to your loving partner, and I guaran-damn-tee that you will be wet as a waterslide in moments. Most of all, don’t think too much about it. It’s not about what it means, it’s about how it feels, for both of you. Good luck! 🙂
Jessica, you’re very much selfish! Don’t forget that he was bi and also loves men!
bim
I’ve always wanted to do this..my boyfriend never lets me play with his butt 🙁
I always cup his cheeks or play with his balls but whenever I try to inch closer he gets mad.
@John This DVD is probably available on US sites, but I’ve heard good things about it. http://www.comeasyouare.com/default/index.cfm/shop/product/Bend-Over-Boyfriend-2/
Also, if you have the Savage Love iPhone app, you can query a subject and look through his archives (you can’t search on the website) for advice on this. A little wine and porn would probably help get things rolling for your wife, so to speak!
Redme, you sound like the kind of woman I would love – peg me hard, sounds lovely. What shoild I do to encourage my wife? Any suggestions gratefully accepted.
Yes, Jessica, you are being selfish.
Peg him hard and he will luv you more.
Besides, with his history he could go back to the real thing back there, so you need to be competitive with a big strapon that WILL NOT GO LIMP!
My husband is bi sexual he used to only be with men but then he met me and the rest is history. He really wants to do the strap on thing but it makes me uncomfortable. he also likes anal with me receiving he doesn’t get that either. He wants a fufilling sex life but I’m too uncomfortable to do any of it, he’s asked about a “friend” to have his way with which gets a big NO. Am I being selfish?
I’d love my wife to use a strapon on me. I’ve even bought her one but she seems to not want to know. I’m a lot bigger than her but I’m sure that she would enjoy it once she started. I have had a vibrator in ther before so I’m not that tight. How can I encourage her? Any suggestions, please!!!
@ben mello
Easy on the solid foods that day works for me. (I tend to stick to soups and salads… and alcohol!?)
Have an bowel movement an hour before or so. Wipe yourself down before you end up in bed. Bring a towel.
It is the down side of this sex act, but if you’re clean, it shouldn’t be an issue.
Good luck!
DEAR STEFAN, IF YOU LUBRICATE PROPERLY AND BEGIN BY INSERTING SMALL THINGS – LIKE A PINKIE OR A THIN, TAPERED BUTT-PLUG, YOU SHOULD BE FINE. DON’T JUST TRY TO JAM SOMETHING BIG UP YOUR BUTT.
I AM 17,AND I HAVE A QUESTION,FOR THOOSE WHO HAD STRAP-ON SEX: DOES IT HURTS THE FIRST TIME?I WANT TO TRIE,PLEASE ANSWER,ANY SECOND REACTIONS CAN HAPPEN?BLEEDIN OR OTHER?