Our contributor, a woman named JW, 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:
“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.
June 30th, 2010 at 4:56 pm
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!!!
July 3rd, 2010 at 5:53 pm
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?
July 3rd, 2010 at 8:56 pm
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!
July 5th, 2010 at 5:27 pm
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.
July 5th, 2010 at 10:37 pm
@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!
July 7th, 2010 at 10:15 pm
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.
July 8th, 2010 at 6:28 pm
Jessica, you’re very much selfish! Don’t forget that he was bi and also loves men!
bim
July 11th, 2010 at 6:01 pm
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!
July 11th, 2010 at 6:06 pm
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.
July 14th, 2010 at 9:41 pm
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?
July 15th, 2010 at 11:25 am
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.
July 16th, 2010 at 6:16 am
wow,i wish i could find a woman like you,I just love butt plugs and dildos
July 20th, 2010 at 9:50 am
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.
July 20th, 2010 at 4:34 pm
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.
July 25th, 2010 at 11:34 pm
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
August 10th, 2010 at 12:33 am
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?
August 10th, 2010 at 11:07 am
^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.
August 13th, 2010 at 9:24 am
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
August 17th, 2010 at 2:09 pm
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.
August 20th, 2010 at 5:04 am
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?
August 20th, 2010 at 8:36 pm
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!
August 22nd, 2010 at 6:06 pm
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.
August 24th, 2010 at 9:21 pm
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.