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.
Ok, my boyfriend have been dating for 5 months, and he is very sensual soft and sweet…one morning i was spooning him from behind, and i was super horny. he knew it, he kept pushing his rear into my pelvis and eventually i started to push back and things got hot, i began thrusting into him like doggystyle(low) eventually we got wild and he was grinding on me like a girl in a reggae video, it was hot i have to admit. i also gave him a hand job while i got off on his upper thigh, and my right leg was thrusting into his rear, he loved it! like he was rough a bit and very into it, i was surprized…. and then he shagged me missonary and it was nice…HOWEVER, since that new, hot sexy steamy kinda akward moment we havent tried it again, but i know he thinks about it, it was amazing… we are living in diffrent cities for a month right now, and i will be seeing him really soon, but i want to know if anyone has some advice for me to initiate that experince that again with him, i want to try to please him anal, it turns me on so much its crazy! but at the same time i worry if he might be turned off????? or if that means he is a little bisexual…what do you’all think? 😉 its exciting and new, and very hot. i love this. cheers
Ive fantasized getting pluged from behind for years. Now me and my girl went from finger, to plug, to strap on. and i fucking love it.. I throw some panties on to for the extra thrill of the taboo breaking..
And no i aint gay….
I like that your boyfriend was open to the idea. =) Practice does make perfect. And I think the more willing the person is to try it, the better the experience will be. It’s nothing weird or disgusting at all. I think the idea of anal scares most men and women when they first think about trying it. Men are mostly hesitant to the idea because people have led them to believe it’s a little gay. Women I think have endured bad first experiences and shut themselves off to the idea completely. Honestly, if you and your partner are really comfortable with one another, anal shouldn’t be something feared. You just have to be very gentle, relaxed, and open to the idea. Otherwise you’ll have a bad experience. My husband and I have anal sex often enough. The first few times were horrible experiences because we didn’t understand that the people in porn actually do get prepped and ready for their takes. o.O Yikes… lol. But after we got it down, it’s been something very sensual and kinky to do spontaneously. As for him, he’s actually the one who suggested getting a dildo and doing him from behind. When I first attempted it, I laughed a little thinking “I’m the man” lol. But once you get started, the girl really gets into it. I think it’s a controlling thing. 😉 You should try maybe having him bent over and jerking himself with baby oil while you make love to him from behind. Grab his hips and do it gently and lovingly. And then maybe, if he’s making pleasurable sounds ask him if he would like you to be a little more rough. =) My husband doesn’t request anal every week. But in the times that he does want me to do it, we do as stated above and he ends up orgasming and loving it. Just do what you’re doing and make it fun and sensual. Your guy may not end up loving it, but he may want to do it on rare occasions if he’s had a good experience in the past. 😉 It’s great that he’s up for another go. Hope all goes well. =)
i love my by friend<3
Bill
if not done yet, try giving her anal sex and graduate from there, have her to touch you behind your balls when making love…make sure she knows you love the sensation the nearer she gets to your anus… also maybe involve some porn movie watching that slivers to the theme of what you want,
i was introduced to having a finger inserted in me several years ago while having sex, done at the right moment…although a suprise was quite enjoyable and as OP stated us men have regions that can make us orgasm that we dont know about. and hey!! gay men are not stupid – they know more about thier own bodies than most heterosexuals. now years on recently married, my wife has a fantasy of doing me from behind, of course she hasnt been there yet and ive not informed her of my sexual activites from prior relations (obviously) so im currently looking for a strap on for a present for her..im not going to meddle with a plug..its not what she want or fantasies about…just hope to god i like it just as much as she will…good luck all and thanks for your coments..interesting read..x
My guy wants me to try this out. I’m totally into trying new things but I’m a but nervous. Any suggestions on how to start and what guys really like?
My girlfriend and I have tried the finger thing. Last night she inserted a small vibrator and I (thanks to the drinks) begun to enjoy it. She then inserted a bigger one that I use on her and I was scared and nervous. I didn’t want her to think badly of me. She then did the whole thrusting thing and it excited her. I have to say I enjoyed it. Still timid and nervous about it but willing to try again. I assure you I am a straight male but the taboo thing is what is getting me the most. But overall she made the experiance wonderful because I knew it was her and saw her enjoying it as much as if not more than me.
Best experience of my life, tryied it with my ex girlfriend about 10 years ago and just loved it. I had a strap on sent home for her… She wasn’t sure at first but got use to the idea.. We did it many times till the relationship ended. Since that time i had many experiences, by myself (anal plugs), with new girlfriends, with shemale (i had to try the real thing…) and OMG best ever!! Now i’m married man and wife doesn’t care at all about anal play.
It really turns me on, not sure how to convince her.. Any idea??
It is an amazing feeling. A girlfriend about 25 years ago had a vibrator and put it up my butt when we were having sex, thought my toes were going to fall off. As toys became softer and more real and met more adventureous women I was hooked and pegged. I would like to get it done more often. Unfortunately it is now hard to find a woman who is secure enough to wear one. I live in the NYC are and one who think there would be enoungh willing women …. NOT
great to hear people are trying out those hidden pleasures!
Well took me a couple of years to get into the idea from an initial student surprise and breaking down bedpost … common grounds… I think describes it best
I mean a confident sexual man loves a little butt action, not sure on the strap on yet, but we will see. Im guessing so thou as he is a little dirty son of gun, 🙂 and Im his little dirty girlly.
Ty
This is the funniest thing I’ve seen bahahahahahahha
A lot of guys yearn for this. Nothing beats great anal. You will own a guy forever if he wants this and you please him this way.