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 am a 25 y/o guy, who’s recently managed to get his gf to let him do her anally. and as time wears on she loves it more and more. I get told all the time I have a great ass. she’s quite timid and the thought of her banging my tight ass makes me hard right away. Great role reversal, but being a bit old fashioned, I don’t know how to bring up the topic? how do I conquer the final frontier!?
You guys/gals should be so happy to even have a spouse who enjoys being sexual. Some of guys have wives who pretty much don’t even enjoy sex. Oh my wife loves for me to rub her butt, give her massages, and if everything is ok in her work life, she let me have sex with her… but she thinks she is doing me a favor by laying down and letting me do her. Even though she doesn’t do anything back… it’s like she is a blow up doll.
I tried to rub her anus once while she was all turned on and she asked me to stop.. so of course I did…
She wouldn’t even think of fingering me, even though I;ve told her that if you finger a guy while or just before he’s orgasms, it is like 10 times more powerful… but she just sort of shugged, Oh that’s nice…
So don’t think you have it bad just because your wife won’t do you in the butt. It could be worse.
My guy won’t let me use anything other than my finger. I don’t know what it is if he doesn’t feel comfortable enough, what it is. He says he likes it, I don’t get it. I don’t think its gay and what’s to categorize what’s what. I think any guy willing to try new things is just worth being with.
I am a guy and my ex-wife use to finger my ass while giving me a blow job. I loved every second of it. I wanted her to get a strap-on and fuck me with it, but I didn’t know how to let her know, I didn’t want her to think I was gay. Well after her, a few girlfriends and another ex-wife, I met another and decided I wasn’t going to get involved with another women without telling her what I wanted. So I told my girlfriend what I wanted her to do and she said, well I have never done anything like that before but ok I’ll try it. So I bought us a strap-on and she tried it. She felt funny at first and so did I, the next few times we got more into and she got more and more into it and now she loves being in control with her strap-on, making me bend over the bed, the couch, the chair, on my back legs up and now she wants to start doing me outside like, bent over the fender of the car, bent over the motorcycle, bent over the ATV and of course, she wants to do it up in the mountains. I think I just may ask her to marry me.
my boyfriend does this all the time… it’s GREATTTTTTT
KC do the fingering, then slip him something a little more. Start with something just slightly bigger than your finger and work your way up. If he likes the finger, he will go for the toy. You could always watch some videos together or slip him an email with a link to a nice strapon video.
So I really want to do my husband with a strapon but not sure what to do to get him to let me. We have been together for 5 years and married for 3 and I brought it up once before and he said no. Since we have been married he has let me play around there with my fingers while I’m giving him head, but I really want to take it to another level. I am not sure how to bring it up again :(. A couple weeks ago we went to a local sex shop and he stopped and looked at a strap on and it made me wonder if he was thinking about it. I have made him orgasm while fingering him so I think he would like it but how do I get him let me try toys??? Any suggestions?
My wife fucks me with a strap on about once a week. We both love it.
Do it! We have played with fingers and dildos for years, then we did it … wow! My wife gets an inverted nipple when she gets really turned on and is an occasional (2 x per year) squirter. She put the strapon on, left nipple was inverted. I climbed on top and rode her strapon – she was gushing within 2 minutes! It was fantastic! We don’t do it all the time, usually only special occasions, but it is a great turn on for both of us.
I love it, just wish my wife would do it more. I love when she’s in control and she’s really good at it.
The first time I was about 18 and my girlfriend at the time used her fingers everytime, but she wouldn’t use toys or anything.
Then when I was in my thirty’s out at the bar ran into that old girlfriend, got talking one thing led to another back to her place we start messin around and she asked ” did you like when I used my fingers on your ass” I said hell yeah. needless to say she went to the bedroom called me in 5 minutes later and she was wearing a strap-on.
I wasn’t sure I would really like it seeing that it was bigger me, but I did and still do.
I can’t wait till the next time she’s in me.
Ashley, why do you enjoy that??
This letter / confession ended with some useful information, but ugh, if those were the actual words she used the first time she raised this subject, it’s no wonder her boyfriend wasn’t interested — the way she talked about it was extremely, extremely corny! Fudge-packing? Come on, who talks like that after age 10? So not sexy. Maybe it’s just me, but I think if you’re going to ask a partner to try something new, the best approach is: try to make it sound sexy. Like something two (or more) consenting adults would enjoy, not like a cheesy elementary school joke. And on a related note, ask at an appropriate moment. I hadn’t considered that aspect of it until I read the comment above saying “It is a very awkward dinner conversation.” Umm, yes, it would be — why on earth would you choose to have that conversation over dinner instead of, say, after some good non-pegging sex? If you want something sexy, ask sexy — not while sharing a pizza.
Oh, and some advice for the Boston commenter above, the guy who says he’s a jock and is afraid to ask the sort of girls he knows to peg him: This is provoking another umm from me. Have you really not noticed that the sort of women who tend to go for jocks do in fact tend to be quite conventional? Compared to, say, the kind of girls who tend to go for hipper guys? Cultivate a more complex personality, one that can’t be summed up as “jock” (or any one other word) and you will find yourself meeting a wider range of people. I don’t mean to say that all girls who date jocks are super-vanilla in bed but . . . uh, actually, yeah, as a woman who has avoided jocks all her life, I do kind of think that about them. They just look and act so traditional and risk-averse. I’m probably wrong (I hope I’m wrong) but still, I think you’ll have an easier time finding women who share your interests if you aren’t the sort of guy everyone looks at and thinks “oh, a jock.” Read some interesting books, go to some arty movies, stop popping your collar, etc. etc. etc.
Well I am 18 and my boyfriend wants me to do stuff with his butt. My problem is we have never done anything before like that and I don’t know what to do so we can ease into it. HELP!!!
My ex and current wife have both pegged me before and it was great but it was hard to ask. It is a very awkward dinner conversation.
MMMMM my ex did me in the ass years ago a couple times.i loved it.her ass was exit only-and she had a fine ass.i want it again,i’ve been in chat rooms and had online Mistresses that would Domme me and cyberly use a strapon on me.now i’m about to meet my current Mistress r/t.she is a young black Mistress and very kinky.i can’t wait to meet and get my booty buggered.we are both switches so i’m gonna do my Mistresses ass too!MMMMMM