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.
My girlfriend has been pressuring me into doing this for a really long time. She even bought the strap on and everything. After awhile I began considering it so I decided to masterbate one night with a dildo up my ass to see how it feels… it actually turned out to be an amazing orgasm. But when i pulled out the dildo there was some shit on it… basically im open to letting her do me with a strap on but i dont want her to pull out and there be shit streaks on the dildo… thats just nasty. Any suggestions?
The first time my ex asked me too I felt kind of weird about it. But then seeing him arch his back, hearing him moan, I got so wet. Since I’m married I’m hooked.
@Jonathan. You might start with at discussion about “G” spots and how men have the equivalent “P” spot. It’s all about the nerves and stimulation. I think that direction doesn’t scare a woman thinking “OMG, my boy is gay!?
Go from fingers to dildos and once she’s comfortable with a dildo in there maybe she’d like to have a free hand and having her strap it on. It might/will take time. You’re changing a big mindset. Some women don’t even like to acknowledge they’ve got an anus never mind, that you’ve got a super sensitive anus. (I really don’t think women can get the same excitement from anal sex as they don’t have the ‘same’ nerves there. I don’t know.) But once they know how sensitive it is for you… it’s all up to their willingness to please you.
Keep it clean and she’ll have nothing to object to.
Has any one got any easy way of getting the subject across to the wife .. And getting her to do it with out to much presur on her
@ boboskee, I see your worry. But does he like getting blow jobs too much, or regular intercourse or ??? I really won’t worry about it. It’s just part of some kinky sex play between the 2 of you. If he does like it too much, well, it’s him liking it with you.
I love intercourse. I like getting blow jobs. I like going down on my wife. And I love it when my wife pegs me. I trust her.
But If I was going to cheat, I don’t think I’d be asking someone to peg me.
ive deffinatly wanted to do this with my bf…we talked about it a few times and i really love playing with his ass and he loves it too… but im scared he might like it too much?
Henry and SS, I agree same sense of loyalty and trust!
Wow, that’s a really cool comment. Re: your question, maybe it isn’t one or the other, maybe it’s both, plus a lot of gratitude that she does that for you. Maybe knowing that she has the power to not do it at all, or that she could hurt you if she wasn’t careful, but instead makes it an incredible experience for you just leaves you feeling awed by her. You guys are lucky!
My wife and I did it last night. I’m no virgin. Married 11 years we’ve done this on and off since we got married. We just haven’t done this in maybe a year.
I wanted to throw a question out there to the ladies… and the men that have been pegged.
Afterwards, after I’d had a huge orgasm from her massive toy, I felt “owned.” I felt that I was definitely a possession of my wife’s. >>> I’m not saying subservient or submissive, just an incredible loyalty.<<< I was her boy. My trust level in her and love for her was off the charts.
Here's my question, from the orgasm, or the penetration?
He’ll yeah dude
I waited thirty years after I first saw it in a movie when I first asked my wife she didn’t want to at first but now we do it two or three times a month. due to back injurys I am left with reduced feelings in my penis. but when she pegs me it’s like it was before,hard intence orgasm. the added thrill is she loves it and useally has up to ten or more orgasm while she’s doing me which i love. It has put the thrill back into our lives and no i have no urge for implants our to go to the local truck stops i just think it hot and sexy to see my wife wearing her (cock) and waving her finger at me and saying it’s time to bend over baby
^I’d say that happened because your ex was a closeted transsexual, ams, not because you “turned him into one” by pegging him.
Please be careful ladies…my ex-boyfriend and I did this alot! Then it turned into him dressing up like a woman…sneaking out and meeting men at truck stops to give BJ’s and now he wants breast implants and only likes anal sex! It was fun and kinky at first but then it took a turn for the worse. We did it for about 4 years and it destroyed our relationship and broke up. BECAREFUL because it does change your relationship!
I want to do this to my boyfriend but whenever we talk about it he is very adamant that he will never let me do it. The thing is he has let me use my fingers and I could tell he really enjoyed it, he even let me use a vibe plug which seemed uncomfortable but he still appeared to like it. Whenever I aske him about those instances he says that he didn’t feel anything and only lets me do it b/c I want to him to. I know he is lying. I have told him that it doesn’t mean he is gay and that alot of men like their prostate stimulated. He just is so difficult about it. I rreeeaaallly want to do it I don’t know what will happen if I can’t fulfill this fantasy I might quite litterally explode. His ass is so perfect and beautiful I want to fuck it. Help me please, I need advice.
Looks like EM & Lo need to have a matchmaking site from people who like to peg. I am a single girl w/a strap and no one to strap it to! Like ships in the night, we may never meet!