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Author Topic: Confession: I Want to Do My Boyfriend with a Strap-On  (Read 2689 times)
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« on: March 12, 2009, 10:01:32 AM »

repost from Em&Lo.com

Jessie Whitfield, a psych major at Arizona State University and blogger at [urlhttp://www.bsnatch.com/]Bsnatch.com[/url], 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 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:

“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.
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Roadie
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« Reply #1 on: March 13, 2009, 05:10:53 AM »

I, too, was a little uncomfortable with the prospect of having a dick in my ass, too. But, I too, felt that it was only fair...I have done Dreamer in the ass, she should be able to do me. We got her a strap-on...and used it. I did not have any uncomfortable, uneasy feelings. But I also did not feel my prostate being massaged. Dreamer did get a nice clit rub...but no prostate rub.

People have called me an ass hole for so many years, maybe my prostate fell out?
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« Reply #2 on: March 13, 2009, 08:06:48 AM »

Hi Roadie,

A man's prostate is very similer to a woman's g-spot in the way that it's not always easy to find or stimulate. You (like many other men and women) probably need a larger toy with a curved end to target it. You might have Dreamer give you a manual prostate massage to give you a better idea of what it's like. Then, you can replace the dildo in your harness with something more p-spot specific. Here's a re-post of our directions for prostate milking:

Prostate milking can be done with fingers or toys built specifically for that purpose. Naturally, we like P-Spot toys as they offer more targeted stimulation (and less wrist strain!) However, if you want to hitch a ride on your pointer..here's how:

-Preparations: Trim those nails! Bottle of lube at the ready! And should you have reservations regarding playing with your no-no hole try wearing a thin latex glove. No muss, no fuss.

-Start by slowly introducing a 1 or more lubricated fingers into your anus. Relax! Put on a little Barry White if you must. Push upwards and to the back, like you are pushing your fingers towards your navel from the inside. And for the love of God, take it slow and don't treat yourself like a pinata.

-Do you feel a small, round bulb about the size of a large walnut? You've hit paydirt, my friend. Give the little guy a nice how-do-you-do by massaging him slowly and gently, slowly and gently. And, because the P-Spot is so rich in nerve endings you don't always have to press on it directly. Try massaging the edges around it first. Sometimes less is more.

-If you do it right you might suddenly feel the need to pee (even if you just went.) Don't fight it-roll with it. Keep in mind that correct prostate stimulation improves erection strength. That means you will very well end up with a whopping porn-star boner you may want to show off to friends and family. (Don't.)

Keep it up and the area will be so well stimulated that you may actually ejaculate without masturbating.
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« Reply #3 on: March 13, 2009, 03:33:07 PM »

This sounds like an invitation for a finger wave. It's the best of two worlds. Give him head and while you're blowing his mind with pleasure slip a well lubed finger up his ass, find his prostate gland at the base of his penis and massage it. Stroke it gently and stand by for the biggest climax you've ever seen him have. It's wonderful. Try it you'll like it. Hank
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« Reply #4 on: March 14, 2009, 05:39:08 AM »

This is another thing we are going to work on (see post under Oral Sex)!
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human_fighter
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« Reply #5 on: May 12, 2009, 05:23:43 AM »

Hi I'm a guy and anal with a partner is one of my biggest fetishes I love it... finally found a girl as into it as I am and its amazing. Heres some pointers...

The butt is a big place compared to your vagina and unlike the g-spot ripples in a woman the "P-spot" in a man does not always correspond to a specific kind of structure in a man's anus. Some times you need to do allot of searching for the right spot.

Ive found a couple of "points of interest" 1.Just inside the bud if you curl your finger towards the mans testicles like a hook so your digging into flesh and rub or pull up you may get a nice reaction... dont go too aggressive... unlike vaginas butts aren't meant for this kind of thing. 2. About mid way between the first "limit" (where you have to start twisting to get any farther because the colon isn't straight) and the anus if you press up towards the tummy/cock and stroke in and out you will hit his prostate. 3. After the first "limit" if your dildo has a curve or bead at the end rub it against the edge of the "limit" very softly this will either feel good or like a cramp so stop immediately if hes not a fan (kinda like cervical bumping).

If theres a pronounced head on the dildo do something I cal Popping which is to inseart and rapidly remove the end of the dildo stimulating the anus... like the vagina the anus is most sensitive at its entrance though that entrance flares out wards after about an inch so it may be easier to practice popping with a larger headed dildo or plug... also while popping it will help the sensation if he tries to resist or clamp down this will prevent popping but cause the plug to "bump" his inner anus try twisting the plug to stimulate that part of him.

DISCLAIMER: these are things that work on me and as I mentioned I loooove anal all men are different and any or all of these techniques may not be pleasurable to him... remember to communicate and to follow directions to the letter when your in there its fairly delicate and you risk some pretty severe types of injuries if your not careful also remember to use phythalate free toys for penetration and for as much of your sexual contact as possible and use lots of lube at least for the "training" period (first while until he figures out how to properly control his anus to accept your toys).

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« Reply #6 on: May 12, 2009, 01:47:53 PM »

Awesome contribution, humanfighter!
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« Reply #7 on: May 12, 2009, 05:25:34 PM »

It never hurts to help Cheesy
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DJ in LA
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« Reply #8 on: August 27, 2009, 10:47:21 PM »

to be honest, as a male, that would scare the crap out of me!
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« Reply #9 on: October 10, 2009, 04:30:01 PM »

damn she is one hell of a woman
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