3/11/09
Confession: I Want to Do My Boyfriend with a Strap-On

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.

Interested in Your Own Butt Plug?
The Top 5 Rules of Engagement for Backdoor Toys

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582 Comments on "Confession: I Want to Do My Boyfriend with a Strap-On"

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Mouse
Mouse
26 days 2 hours ago

He’s a keeper <3

tom
tom
1 month 25 days ago

If the woman is dominant and the man is submissive and she wants to do his ass then he may as well try to enjoy it because it will happen one way or another. I suspect that many women who like doing this also like to make the man a cuckold just to demonstrate who is in charge.

OH of OH &W
3 months 10 days ago
Love is a two way street. The more you give , the more you get. What if it was the other way around ? What if the guy wanted the girl to use strap on on him ? Should people in a loving relationship not share what they want ? Of course they do already. It’s just that this is not your everyday talked about thing. From the looks of all the strap on’s and stores about pegging on the internet, it is more prevalent than people are willing to admit. Of course it’s not something to discuss at the… Read more »
PointingOutTheObvious
PointingOutTheObvious
3 months 11 days ago
I’m going to rewrite the above article but swap the gender roles, feel free to let me know if this sounds morally okay to you: Our contributor, a man who wishes to remain anonymous, has a confession to make. My girlfriend’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. My dick to be exact. I want to bend… Read more »
PointingOutTheObvious
PointingOutTheObvious
3 months 11 days ago

I get that I missed a few of them, but you get what the fuck I’m sayin

Em & Lo
3 months 11 days ago
Hmmm. You missed quite a few of them. The main one being the line about the narrator having ALREADY been boinked in the butt by the partner! That’s absolutely essential. In the original article, the boyfriend has already been on the giving end of anal sex with the narrator — and now she would like the favor to be returned, for HIM to try to be the recipient of anal play like SHE has already been. That fact somewhat softens the slightly crass goal-orientation of the post. She is not pressuring her boyfriend to do something they’ve never done before,… Read more »
Jon
Jon
1 month 25 days ago
Agree with this. When my gf first mentioed doing me that way my response was no but her argument was you’ve done it to me. Can’t really argue with that logic! Still took a while for me to get comfortable with the idea. For me first time there was a big feeling of being vulnerable being on hands and knees waiting to get it. But as she said exactly the same as for a woman getting it doggy style, so only “fair” for me to feel the same. It’s the sense of getting it rather than giving it that feels… Read more »
PointingOutTheObvious
PointingOutTheObvious
3 months 11 days ago

If this was a dude who had pressured a chick for anal people would be pissed and calling him an asshole, yet people want to condone what this woman did, shit’s fucked up

IveSeenBothSides
IveSeenBothSides
3 months 11 days ago
I’m a 28 year old woman who’s been in 2 serious relationships (the second one I’m currently married to). The man in my first relationship greatly enjoyed anal play (although he seemed embarrassed about it, not because of how I reacted to him asking mind you, I was fine with pleasuring my partner in any way he wanted). My current relationship, ie my husband, is a very firm “Hell no!” on the matter. Now as a woman who’s experienced both sides of the fence…do I think my ex was gay? No. Do I think my husband is a homophobe? No.… Read more »
Em & Lo
Em & Lo
3 months 7 days ago
Like we mentioned to PointingOutTheObvious, the key to this post is that the narrator’s boyfriend has had anal sex with her butt — she is only asking to let her do with him what he has already done with her. So the comparison to a story written by a man pressuring his girlfriend to do something she didn’t want to is not quite fair. The boyfriend obviously doesn’t have a problem with anal sex in general being dirty or gay or something he just wants no part of — he’s previously enjoyed it — he just wants it one-directional, which… Read more »
IveSeenBothSides
IveSeenBothSides
3 months 11 days ago

Just remember if you are gonna do this for your guy ladies CUT YOUR NAILS!!! lol

CommonSense
CommonSense
3 months 20 days ago

Y’all are gay. I’m sorry but if you want or allow anything in you butt for pleasure, you’re gay. That’s like messing with trannys and saying its not gay. Sorry but it is. Real men are becoming a dying breed unfortunately. Mostly weak minded, over emotional, self hating men being raised. This article is Just another way of teaching how to dominate and feminizing men.

OH &W
3 months 10 days ago

Could you please define what a real man is? And what do you think a women’s role is ? Are men and women equal ? Are good relationships one way ? Do as I say ? Or should men and women, husband and wife etc work together and help each other ?

Em & Lo
Em & Lo
3 months 7 days ago

Are men and women equal ? YES. Are good relationships one way ? NO. Do as I say ? NO. Or should men and women, husband and wife etc work together and help each other ? YES

Bklynbug
Bklynbug
3 months 20 days ago

My manly man loves when I do anything to his ass (esp with our Hugo). Being gay means that you’re sexually attracted to the same sex, not whether or not you enjoy anal play. I really think, CommonSense(less), that small/narrow minded people shouldn’t be allowed to wander the interwebs all by their lonesome.

Em & Lo
3 months 20 days ago

Hugos can make any man a convert: https://www.lelo.com/hugo

Em & Lo
3 months 20 days ago

Sounds like someone needs to read this: http://tinyurl.com/h99nvqo

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