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’m glad to see that other women are turned on by this as well. Hubby and I do anal paly on him, not all the time but it is one more thing to add to our menu. Sex should be fun and as long as you both are having fun then there should be no limits. Go for it!
It is an incredible sensation. Seriously, the prostate is electric!
I had to laugh at Gloria’ experience… guys kept emailing her for weeks thinking they could get some. I understand the desire. However, I think having a strange woman* “do me” would be unsettling, however truly trusting someone, i.e. my wife, leads to some mind blowing sex.
Lube lube lube and just take over and do it.
*and I wouldn’t even think about going gay for a guy to do. Not an option.
Yes, back door internal is hugely different.
One way to approach it is to use your finger first. LOTS of lube and very short fingernails or a good latex glove so your fingernail does not do any damage.
Put your index finger in and carefully feel for something that feels about like an almond or a walnut. It is only 2 1/2 or 3 inches inside of his anus.
Once you find it massage it very gently. Too much pressure will hurt. Ask him to tell you if you need more or less pressure.
Hit it once and watch him go crazy! Then go to aneros.com and order him one of their prostate massagers. Probably the Helix is the best starter model.
There is a forum on the Aneros website that has tons of information on it. Let him do some reading there and he will get more comfortable with it, especially when he finds out that he can have multiple orgasms instead of just one!
PROSTATE FANS
Can’t I do external stimulation on my man’s perineum? Is back door/internal that much better?
omg,,i thought i was a freak of nature cuz i love messing with my boyfriend anus when we have sex…i love it..it gives me a great sense of control..i love to kiss and lick it…ive fantasized about putting on a atrap and stick it in his ass….
my girl loves to play with my ass she likes to be in control and i love being at her mercy she had introduced me to it with first a finger then she used a small toy before u knew it i was begging for a big strap on i could not believe i would ever enjoy it but i love it and she gets great pleasure and often orgasms during strap on sex it is some of the most powerful orgasms i have ever had i would recommend puttin your phobias aside and go for it
Here’s a question for the ladies. I LOVE having my prostate tickled by my wife. She uses the Aneros on me and my orgasms are AMAZING, but I don’t get the feeling she is enjoying it. Id consider a strap on for her but would that give her any sexual satisfaction?
Oh dnot worry. i am a straight dude, and i finger and stick homemade toys(mostly bannanas) up my ass all the time. i love the pain as it goes in, and the stimulation i get once it’s in there. i useually cum very quickly. email me if you want some tips.
Okay this was very interesting. I am a reciever from my wife and love it. Sheis so hot and I feel her up as we go along, and boy is she wet. The wordsare hot too. Try it on your next go around, you may not have to even touch the manhood.
Practice makes perfect…. Loved the Grey’s Anatomy reference!
Ohhh… other than use of the words “peen” and “vajayjay” this is a great post. I mean, what are we, 12?
I have been on the other side of this. He wanted me to poke him with the strap on. He didn’t go through the scientific explanation but he did I would love it too. I did some research on my own and found a wikipedia article. Then I looked on craigslist and saw there were far more man ads than woman, lesbian or straight.
I watched a couple of “instructional” videos and the idea of putting him down doggie stile (which i like for myself) or with his knees around around his ears and maybe jacking him off at the same time started to really appeal to me. But I didn’t tell him that yet.
I actually talked to a couple of these guys on CL, then they wouldn’t leave me alone for over a month. Good thing it was by email and phone. I talked to two girls who put a woman for woman ad and they told me only one in ten who answered were female. mmmmmmm………….
I finally did put him down doggie stile and other stiles too! mmmm……mmmmm…… And he thinks I’m doing him a favor! I wonder what I should ask for in return ;-)~…….
Daniel is correct, and I’m sorry I didn’t make any recommendations myself before. The Aneros, or another toy curved specifically to stimulate the prostate, will do much more for his enjoyment and the possibility of progress towards pegging.
This is such a coincidence, my bf and I only just started doing anal play. He was a little nervous as first too, but he really likes it so far. We just use fingers, I think it feels a little more personal. But we may branch out!
Wonderfully well written. I hope we get an update in the future.