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.
Funny, this might be one of the top two fantasies for perfectly hetero guys. Its not about being bi or gay, its about understanding what a woman feels and about the whole prostate thing. A prostate centered orgasm is unbelievable. It would be a blast – too bad I can’t figure out how to approach my conservative sweetie to try it.
i would like to shave and wax myself, wear false breasts, then a vstring and put on all female dress and act as a complete woman. this is my fantasy. then my wife should dress as a man and pamper me as “his” woman and enjoy me forcefully, penetrate me or do anything that can be done to a real woman.
Wow, that is hot. My wife got me into anal sex. Moved on from the strap on and have actually had the real thing. I love it. There is no more intense orgasm than when a dick (real or fake) is hitting my prostate.
Ive always wanted to get my wife a girlfriend, shes reluctant unless I agree to her finding me a boyfriend. Thats one way to shut a guy up.
As far as that kind of kinky sex, she did do that digitally to me once. It was..a unique experience. Sure kept me from cutting loose for a long time.
I am not gay, But I could only dream of my wife touching or even entertaining that thought of performing such things. I’m not even allowed to touch her butt crack let alone anything else. 🙁
I decided to let my girlfriend know that I was curious to see what it felt like. She was pretty surprised but she decided to give it a shot with me. I have to say, It was the best experience ever, lol. Better yet, she refuses to let me do her in butt! She doesn’t want it because she has nothing there to make it feel good. Whatever, everyone has there own choice. She likes doing me though!
My wife uses a Feeldoe dildo and says that she cums really hard. I am pretty sure she has squirted while doing me. It is a little pricy, but it is so much better when both get off.
My wife and I have tried this. We both really liked it and want to do it again.
After a few years of me performing anal play on her, she recently suggested doing anal play on me. I didn’t take her seriously at first, but when I realized she was serious I agreed.
The first time, I inserted a well-lubed vibrating bullet into myself and handed her the controller. I had used the vibe on her before. She turned the vibe up and down and we took turns jerking me off until I came. It took a little longer than usual because the bullet felt odd (good, but odd).
Over then next couple of weeks we did that again twice and decided we wanted to go further. She and I shopped around online and bought a strap-on harness with a beautiful glass dildo.
A few days later, first I slowly worked the glass dildo up my ass, then she worked it for a while, then she put on the harness with the glass dildo in it and she had me bend over the bed and smoothly slid herself into me. I couldn’t believe how powerful she seemed!
Slowly, then pretty hard, finally really hard, she fucked me from behind while I jacked off. She really got into it. I was tense at first but soon I just let go and accepted it. After a few minutes, she bent forward, pressing her front against my back. When I felt her breasts touch my shoulder blades and her tongue go into my ear, it sent me over the edge. She stayed still inside me until I completely finished cumming, then gently and slowly pulled out. She took off the strap-on and then we kissed and spooned off to sleep.
That was about a month ago. Maybe I’m imagining it, but it feels like we are closer to each other than before. We both want to do it again.
To Drew who asked how: if your girlfriend likes receiving oral, and if she likes being fingered while receiving it, start making it a habit to let your pinkie brush against her taint and anus while you’re pleasuring her. Don’t make it the main attraction, but just a little spice. It will add a lot to her pleasure (my wife orgasms sometimes with only clitoral + anal stimulation) and I doubt she’ll object. If she does object, back off and come back to it more gently later when she’s totally enjoying herself.
After she accepts that, you can press more firmly on her anus with a well-lubricated finger and/or tongue her a little down there. Try just a little at first, switch the focus back to just her vagina and then back to the vagina + anus.
When she’s comfortable with that, you can tongue her ass more directly and/or insert a finger partially inside her. From there, work up to tongue fucking her ass deeply for a longer time and putting a finger all the way in. After she is enjoying these things, two fingers and then your cock. Be patient! This process took me over a year with my wife. The wait was worth it!
Also – hopefully she loves your cock like my wife loves mine. Rub it gently across her crack and against her anus sometimes before inserting it in her vagina from behind. Slide it between her cheeks and have her squeeze you between her cheeks.
Of course, be sure to find out what she wants (favorites and fantasies) and give it to her! Hopefully she’ll want to give back.
Anyway, thanks for sharing this and to everyone for the great discussion…
Reading this, I realised I was in an INCREDIBLY similar situation.
My real name is zarina, so that made it even more shocking.
I’ve always wanted to perform anal actions on my husband Raju, and infact we agreed mutually, which enhance sexual performances.
I finally convinced him in a similar way, and during the week days like saturdays etc. we have nice drinks and food and after that he gives me a chance to strap on which is about 8* and i have selected the same for him and i just removes the clothes and strap on and raps him with little lub in his anal , during that night we enjoy a lot and he acts as my wife and i as a husband , this secenarion he has agreed to continue for all the days / nights at home only so now i am the bos and he is my slave wife, we will enjoy this for a while and later on think about having a baby with me ofcourse.
Wow, what a hotbed of views! On a more serious note though, I firmly believe that there are deeper issues for any couple to address here.
Firstly allow me to clarify that I am not homophobic, nor do I have any unresolved “gay issues” (a term which in itself I find rather offensive).
The issue of submissive male penetration is one of the very last heterosexual taboos, and while pleasurable, has to occur within certain boundaries in a relationship.
To give you a little bit of background, I am a very happily married man, a father of 3 beautiful daughters, and fortunately, somewhat open-minded when it comes to the issue of sexuality.
Prior to my marriage I had several sexual experiences and relationships with transgender women (or shemales for those that wish to offend) which often, though by no means always, involved being penetrated by my partner.
My experiences with transgender women were an important part of both discovering, and accepting, my own sexuality. After these experiences and relationships, I was able to understand that, while I enjoyed a good many aspects of “homosexual” sex, and enjoyed a strong sexual attraction toward transgender women, I did not have the same romantic attraction to other men, or transgender women, that I have always held toward women.
And for me, there-in lies the crux of this issue. Sex is, put simply, an adults playground. Some rides we love, other’s we hate, and some we like without wishing to admit so.
My wife and I have enjoyed, on a good few occasions, her use of a strap on, on me. The important thing is that she and I both understand that there is a difference between sexual enjoyment, and romantic interest, and for whoever may read this, that is the most important thing for you to decide.
As I stated earlier in this post, I have not had simple sexual encounters with transgender women, but on 3 separate occasions, committed and faithful relationships (as far as I know..lol!) with transgender women.
While these relationships offered me the opportunity to realize some of my “non-hetero” sexual desires, they confirmed for me that I was not gay, nor was I romantically attracted toward men.
There is no shame in enjoying any sexual fantasy you desire (frankly I look at many of the acts performed in the BDSM scene, and wonder how on earth anyone can enjoy that!), the point is, not to judge, and to be comfortable with whatever makes you feel good! (even if that means taking a cock in your ass!).
Ladies, as much as Paul’s comment above about surprising your boy with a strap on is incredibly sexy, my advice would be to tease a bit during the day or maybe the week before saying “you’d better be ready, I’m gonna do ya” just so he can “prep” himself.
I personally don’t eat much in the way of solids during the day leading up to anal sex. We generally have less … shall we say … problems … when we do it.
God, I wish/hope she does me tonight.
My wife used to finger me. So, one day she asked me if I would like she buys an strapon. I got an inmediate erection smiled and said: Yes! After about one month we were near to a sex shop and I inveted her to come in. Now, let’s but the sttrapon, I said. She choose a big one, and I said “do you wanna kill me?” So, we bougt one about 18 cm.
GOd, I love it. I love to see her useng a mini dress with it hidden, we make a scene, pretend I dont know or she really makes a surprise, and after a lot of prelimiraries, she says: “turn back”, and she does me. I have incredible orgasms and scream a lot. Now, I have 4 dildoes one of them is about 23 cm, and I like them all. I love see her wearing that strapon, specially because she’s very angelical and it’ is the great contrast.
An advice: If you wanna do your partner, do not ask him: buy an strapon, and make him a surprise under pants, skirt or dress. If you are sure he loves you, and you love him, there are no limits and he will accept your fantasy or try his.
just tie him and blow him start rubbing his asshole and start pushing using lube and he wont stop you trust me thats how she started fucking my ass now she has a 10 inch strap on we love it. but i had to give up some power for it to work
I use a strapon on my husband and he loves it.I call him my little dick bitchboy.He loves me to take control in the bedroom.And if we have a fight it always seems to make everything better.
After weeks of asking my boyfriend finally gave in today!! and when I commenced anal research, I found this article! amazing! I’m so happy he trusts me enough to do this since he is a taurus and extremely stubborn and guess what…..the reason he is doing this is because he thought i was joking all along. Can’t believe he will do this since he considers himself to be a real mans’ man ……so out of character but that goes to show how much he loves me 🙂
I love my cabz