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.
i have ALWAYS wanted to do this to a man. Even reading this article made me incredibly horny, but I’m having the same damn problems as the author. My current boyfriend, whom I love so much, is open to a ton of different things in bed but will not let me play with his ass. I love his soft skin there and the supple firmness of his ass and I try to just ease against his crack but he just doesn’t want it!! I nudge against his grundle or whatever the thing is called, but he seems to sense where I want to go and clenches his yummy little cheeks together.
I love him so much and I don’t want to push it further bc im afraid he’ll feel inadequate or hurt that I’m not completely satisfied. But it also kinda feels like a disappointment that I’ll never be able to explore this with him and maybe NEVER will because I want him to be the man I spend the rest of my life with. I also have the desire to do this to other women but I don’t think he’s open to introducing another woman into the bedroom either and I would never do it behind his back. I’m sitting here wetting my panties with just the thought but unlike most of these posts my boyfriend isn’t open to the idea in the slightest. Should I just give up?
This is so cool, I have never even thought about doing this to my boyfriend but now I cant stop thinking of the right way to bring it up. My boyfriend and I are both very straight, very sexual, and very open. It doesnt have anything to do with being fem or dom or gay or straight, for us it is all about pleasing eachother and finding new things to take our pleasure even further. We take turns being in control and love to experiment.
(This can be used as advice for how to get a girl to do this)
He was the first one to initiate anal play, while I would blow him he would lightly and subtly push my hand down, first it was just his perineum. I had never touched a guy there before so it was strange but exciting. I got very into it because I saw it turned him on which in turn turned me on.
After about a month of blowjobs with that kind of play he pushed my hand down further towards his butthole. At first I wasnt sure what to do so I just gently rubbed it. He would grind it against me so eventually I started slipping it in. Just one finger. I love to feel his prostate grow before he climaxes.
Then after a while I started licking his perineum, then finally his butthole. Sometimes he lies down and I do this but we also do it from the 69 position both enjoying oral/anal pleasure.
I think guys who want their girls to go further with them should try this slow and steady approach. Don’t push, make sure there is an understanding that there are no judgments, that everyone is comfortable, and most of all that it is pleasurable for you. It makes me feel so much more sexual and confident when I know my guy is enjoying what I do to him.
I will try to see if he will let me do more, I will try keep you updated! 😉
my guy loves the bondage. a finger in the ass he likes. he wants to try a strap on. i’m nervouse about getting one because we have been there alot. the sex store. i want to do it. but, i also hate how i look after gaining 40lbs in the last 5 years. i was only 115lbs. what should i do ? he thinks i’m sexy no matter what. how can i feel the same?
My wife and I have been married over 30 years and just recently found the pleasure of strapon sex. The rush of her putting on that strapon and filling me up is just so hot. I have never had orgasms so intense. There is nothing gay about it. Take your time and use plenty of lube. The trick is learning to relax and reverse the natural tendency to clamp down. If it hurts, stop. Once you learn to relax the feeling is like nothing you have ever experienced.
@Jay from Denver: You might want to have a look at Dan Savage’s weekly column, (Google it, it’s at “The Stranger,” a Seattle paper online) if you look through his archives, I know I saw something about where people could find like-minded friends…or, you could write to him. It’s a really great weekly column he writes, and would probably answer some questions about how to find what you are looking for.
The same here Brenda. I love to be both a man and woman: Man in normal life, and feminine in sex.
bim
I’m all for the whole pegging thing, and want my girlfriend to try it, but i must say, ^^^ that’s kinda gay.
pretending you’re a female and getting your prostate toyed with are very different things…
i really love my normal life as a man outside the bed room, but indeed i love to be the woman in the sexual relationship, strictly in the privacy of the bed room. i love crossdressing, strap on sex and all that make me feel like a real woman. but my wife won’t agree.
It is women like annie that are fantastic. I understand the fear of it leading elsewhere, but I have been with men before and have no desire to do it again. But I do have a strong desire to find a woman turned on by using a strap on.
Problem is, it is difficult enough finding an honest, open woman who is sane and loyal. Then, ad to that finding one who is sexually adventurous and of course attractive.
I am an attractive young male, but I have little patience for most of the “drama” as we say, from women, so I rarely date equally attractive women. If I could just find a network where open minded, low-maintenance women enjoyed these activities.
Please don’t get me wrong, I am not chauvinist, hell if you think about it this gives women equality in the bedroom. Anyway, I am rambling. Any advice on how to locate women into this would be appreciated
Unfortunately Jay, this is the problem we all face. Few women are open to sex, especially when it comes to strapon sex. They fear that dildo today will bring a real cock tomorrow 🙂
The other reason (and this one i agree with them) is because strapon sex is often allocated with other lifestyles such as feminization and s/m (besides homosexuality/bisexuality that was just mentioned).
With these fears in mind, it is not strange to see most women reluctant about strapon sex, even if it gives them control. In my opinion, the best way is to isolate strapon sex from the other lifestyles. Being a man who loves to explore all things in bed does not necessitate being a transgender 24/7/365. It doesn’t either necessitate being a masochist.
With time, when people better grasp the difference between androgyny and transsexuality, strapon sex would become normal to them, because androgyny itself is normal to humanity.
bim
Hey everyone, Every girl I have dated I have brought this up to.
Not a single one of them was delighted by the idea, and only one of them actually did this. My question is, where can I find women who are into this?
I have no idea how to find a woman who actually would be turned on by this idea, and the thought of a woman who would actively seek this out is my biggest fantasy.
Lol dangerduke go for it.. My boyfriend still won’t let me and I want to try it so bad
Don’t know if this will help. I haven’t heard about prep for the guy here. It can be more enjoyable for us guys if we are “ready”. By this I mean, don’t eat heavy, before, and gone through some clean up behind the backdoor. Doing this can help make it more comfortable, and if he runs an enema to clean out, first it is preperation cause thankfully they are small, second the sensation can be sorta well interesting and third it helps to loosen up, mentally prep for the plunge. Finally it is just cleaner.
Once you are all clean why not start of with some foreplay- a nice rim job to kick off the mood- ladies the fingernails can hurt a lot so make want to run a manicure to get them cut back short. Finally patience- and getting him to relax, once I learned to relax and be cool with it- the good times were rolling.
Now you can try a double sided tool to get you all both involved, and think about a dilation kit, comes with several sizes tools for just this occasion.
Also try to talk before hand and see if he can be more talkative during. For me that is when it turned around, when I went for it and relaxed started moaning and talking about how good it felt- dirty talk done right is a great way to encourage. Hope this helps you out.
I read a blog from oldguy but i dont see it anymore.thanks for the advice.Since I am still exploring with pegging and I don’t think my first experince was that enjoyable for my wife as it was for me.She seemed really concerned of hurting me. the strap on she had was a little to big so we orderd a starter one from babeland with the video bendover boyfriend. I hope it helps us with differnt positions and ways she can reach orgasms while doing me in the backdoor. if there is any women who can help us with other ways my wife can cum while doing me would be greatle appriciated.I haven’t cum yet either.but Ihave only had vibrator once and my straped it on once but it was a great time and I can’t wait for are toys to come next week.
how can my wife really have an orgasm by pegging me