Bend Over Boyfriend

Posted by Jenny
Filed in TnO
May 5, 2007

First thing I learned as a girl with a nine-inch silicone cock between her legs: Don't even bother trying to zip up your jeans; it just won't fit. Now I know how Dirk Diggler feels.

I was trying to get better acquainted with this new attachment to my body because I was going to have to pretend it was actually real and ready to penetrate at will.

I had agreed to peg - have anal sex with a bi guy friend of mine using a strap-on - as an experiment. It'd been a long time coming since a girl had offered to do that to him.

It was my first time doing this and I was pretty nervous of causing him any sort of permanent damage if I wasn't careful enough. I'd consider myself pretty good, giving, game (GGG) and having the switch-up of power was very intriguing to me, which tends to be one of the main reasons many women do it.

The act of pegging can be enjoyable for both partners: men may find stimulation of the anus, rectum, and adjacent organs, particularly the prostate, enjoyable provided that enough lubricant is used, and women may get direct stimulation from the dildo, from its base, from vaginal or an anal "butt plug," or in the case of a form of double-ended dildo, from vaginal penetration on the other end.

How else can a chick get off? A woman could use a secondary vibrator, between the dildo and her clitoris, to get pleasure from pegging. As BDSM practitioners might point out, the act of being penetrated is not necessarily experienced as a submissive act, nor is the act of penetrating always experienced as a dominant act.

Given the stigma associated with anal sex (and its association with male homosexuality), some people, many of them heterosexual, like the taboo or gender-transgressive aspects of pegging. Some girls may enjoy the feeling of having a "simulated penis," while some men enjoy the experience of receptive penetration.

I own a loft bed with five inches of headspace so we had to get down and dirty on my floor. To prepare, he inhaled some Jungle Juice, otherwise known as amyl nitrite, which some sexperts advise against because it is a drug and sex should be done sober. Poppers are supposed to open up your blood vessels and besides causing one to look like a cherry tomato, it's designed to enhance sexual pleasure.

But safety first. Just as any guy would protect their armour, always use a condom on the dildo because it's going into all different places and people. Lube it up for best results.

We didn't end up in the traditional doggie position, but instead he was on top as I was lying down, face up. He slowly eased himself down and instructed me to slowly thrust. It was really hard to gauge whether I was using too much force, but his moans and groans indicated I was on the right track.

"You're fucking me, Jenny!" he gasped. Holy shit, I was.

And as I was thrusting faster and harder, I grabbed a hold of his very real cock and began stroking away at the same time. It didn't take too much for him to finish all over my chest and stomach. And then there was that pause and my eyes were round like deer in headlights.

And then an unexpected burst of laughter came out of me. I couldn't stop laughing - the whole thing was just so absurd to me. No, I didn't get off, although I'm not sure I could've really with the positioning and the concentration of what was happening up top. Still, I really liked being in control and would definitely do it again either with me on top or from behind just to see what it's like.

He made me look away before removing the condom. "Santorum alert. Avert your eyes."

Statistics Canada sadly doesn't have stats on the number of women who peg males, but Savage Love sex columnist Dan Savage notes that "Women into pegging are few and far between, although they do tend to be concentrated in urban areas." I was curious about Toronto's reaction to pegging and posed the question on Craigslist.

Responses ranged from "GROSS!!! No ones getting anything near my ass" to "I am straight, in a relationship, and just waiting for the right time to ask my partner to grip it and rip it. I'm already having second thoughts because of the possible mess it may create" to "While I wouldn't want to deny anyone their pleasure, if the man I'm with requests this, I'd just assume that it's just a matter of time before he's craving the real thing."

If you're interested bending over your boyfriend or husband or guy friend-with-benefits, Good For Her has a whole list of recommendations for selecting harnesses, dildos and lessons on Pegging 101.

Girls, you'll have him pegged in no time.

Jenny is a monthly TnO contributor.

Reader Reviews and Comments

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aaaaaaaand welcome back.

Posted by: Tanja at May 5, 2007 3:22 AM

best. post. ever.

> sex should be done sober.

whoever says this should have their "sexpert" license revoked!

Posted by: kevin bracken at May 5, 2007 6:25 AM

Nice to have you back Jenny. =)

Posted by: Sameer Vasta

at May 5, 2007 8:44 AM

That's all very interesting, but can we skip the x-rated illustration on the front page *please*? This isn't a site I expect to have to view only when the kids aren't around.

Posted by: Stephanie at May 5, 2007 8:57 AM

It's worth noting that CAYA also runs occasional workshops on pegging, which are pretty decent, alongside their more traditional anal play workshops. There's also the video that shares its title with this post. If you can get past just how freakin' strange some of the couples onscreen are, it's pretty informative.

Posted by: Matt at May 5, 2007 9:00 AM

Welcome back, indeed! Great post, Jenny.

Posted by: Adam at May 5, 2007 9:28 AM

Yay, pegging! Thanks, Jenny. Excellent post. It only omits some extra detail on safety, since assplay is always a little more finicky, but I think anyone interested can look that up.

Question is, which is more difficult: convincing a (usually straight) guy that pegging would be great, or convincing a girl that pegging him would be great?

Posted by: Gloria at May 5, 2007 2:04 PM

I'm so happy this came about.

Posted by: Japhet at May 5, 2007 2:06 PM

this looks strangely like a jenny post... omg! it is jenny!! welcome back!!

Posted by: rotenblog

at May 5, 2007 2:54 PM

I've always wondered how one could advertise one's willingness to peg- if you were a brave peg-ee, you could wear a "peg me" shirt, but what about the peg-er? Ideas?

Posted by: diana at May 5, 2007 8:39 PM

Gloria: I think on average, it'd be more difficult to convince a guy to be pegged - the majority of the straight ones I've brought this up to were not interested at all. I think it goes back to girls (for the most part) being a bit more open-minded to embracing homosexuality. Girls tend to be more open to experimenting with other girls while guys like the one from Craigslist say, "EW! No way!"

Diana: Maybe a shirt that says, "I'd *heart* to *pirate peg leg illustration* you."

Posted by: Jenny at May 6, 2007 10:59 AM

Jenny: I think you're probably right.

Also, you have to convince BlogTO to sell that shirt.

Posted by: Gloria at May 6, 2007 11:03 AM

You think you could keep this garbage off the front page? Some people have families in their homes, or visit the site while at work.

Posted by: P at May 6, 2007 5:53 PM

I consider myself open-minded and was not "offended" by the article. But I believe it belongs in the pages of Now Magazine, and not on BlogTO.

Posted by: Maria at May 6, 2007 6:05 PM

"Garbage?" Why/how is it garbage?

Maybe Tim can set up something so that people who want to read the TnO column could just click every Saturday instead of it posted directly on the main page?

Posted by: Jenny at May 6, 2007 6:58 PM

Don't worry about getting "garbage" off the front page Jenny. The graphic isn't something people could glance at and immediately scream about. If you don't like the post, scroll down a few inches and it's gone.

There's always a critic or three Jenny, don't worry about it and don't look for ways to censor yourself when it isn't warranted.

Posted by: Ryan C. at May 6, 2007 7:13 PM

Maria: Why NOW Magazine?

Posted by: Gloria at May 6, 2007 7:19 PM

Somebody say pegging t-shirt? Well, now you can appeal to peggers and Web 2.0 nerds alike. =)

Posted by: Sameer Vasta

at May 6, 2007 9:58 PM

It's not about not liking the article. It's about being able to surf this site in my house or at work without worrying what's going to be there when I scroll down.

Would it have been hard to keep the language appropriate for the first paragraph, not have a cartoon of two people boning each other with strap-on until someone decides to click and read the rest of the article?

That's all I ask.

Posted by: P at May 6, 2007 11:41 PM

This was great! Especially that you got so into it, despite the absurdity in a way, great encourager to all the straight never-pegged-a-guy-ladies (but maybe someday?) reading this!

Posted by: Danielle at May 7, 2007 1:08 AM

Gloria: If you read Now you'll see that it is the type of content in that magazine, that's why I said it.

Posted by: Maria at May 7, 2007 7:41 AM

Yeah... it's basically a lightweight first-person account of the stuff that you'll regularly read in Dan Savage's column, right down to the use of GGG and santorum. Yawn.

Posted by: X at May 7, 2007 12:10 PM

Maria: Maybe in the back of the paper? Not sure how a person describing herself as "open-minded" would characterize NOW as particularly raunchy, any more than the rest of the alt weeklies out there.

Posted by: Gloria at May 7, 2007 1:10 PM

This is pretty mild and who has their kids leaning over their shoulder anyway?

Posted by: Japhet at May 7, 2007 1:27 PM

Bahah! That is a GREAT t-shirt Sameer! It has to be made!

Posted by: stung at May 8, 2007 1:03 PM

Hey,wait a sec, Im an attractive strait guy and I would love to get pegged its just role play. Any takers? lol

Posted by: micah at May 9, 2007 9:59 AM

I'm a str8 white male from OZ & I'd luv 2 get pegged by a girl. Just don't know how to bring up the subject of "pegging" with the girls??? I'm concerned they'll freak out!!!

Posted by: boyFromOz at May 10, 2007 6:14 AM

Maybe start small -- ask for her to stick one or two fingers up your bum and go from there. Have a frank talk about why you'd like to peg you (maybe it's "Honey, I really like you to hold the reins this time.") And work your way up to a level that's comfortable for the both of you. Pegging probably isn't a "first date" kinda activity, though.

Posted by: Jenny at May 10, 2007 11:33 AM

Re: Jenny @ May 10, 2007 11:33 AM.

Thankyou for the reply (& tip on raising the subject) from a girls perspective.

In reference to yours (& some of your poster's) above comments from _some_ boy's not wanting to engage in pegging. I suspect that there may be many more boy's that are into being pegged but they probably won't dare discuss the subject with a girl unless they _absolutely_ trust that they can confide in her (i.e. she won't tell others). Her telling anyone would be far worse than her saying "no". Heck, I'd rather be dumped than her telling others! A boy is far more comfortable bringing up the subject of spanking (of which I like) to girls rather than pegging.

From a str8 boy's perspective, let me say this, when I think of pegging, I think of a woman taking control & assisting me in reaching a higher level of orgasm, therefore, I _don't_ think of a man. Having said that, it's not all about the girl being in control. Depending on the position, it could also be more intimate (e.g. boy laid on his back with hips & legs up, girl on top leaning forward).

I can't vouch for all boys (given that we're all wired differently), but I can say for me that that the stimulation of the prostate & nerve endings is incredible! My erections are harder/bigger, the orgasm & ejaculation is stronger (tip boys: drink plenty of fresh water for your ejaculations & body in general).

Finally, pegging is a subject that some boy's (like me) may find absolutely hot! Any girl that wants to peg boys & finds one who's into it, is in for some serious fun!

Posted by: boyFromOz at May 10, 2007 10:27 PM

\jungle juice ..is that "powerpoppers"?

Posted by: Horace at May 19, 2007 9:07 AM

According to my coworker, every boy he knows who's done it LOVES it.

I'd definitely give it a try.

Posted by: Japhet at May 20, 2007 4:15 AM

OMG... The United Pegging Association (UP-Ass) is on Facebook!
http://www.facebook.com/group.php?gid=3211125011

Posted by: UP-ASS at June 5, 2007 10:39 PM

Unfortunately, a large portion of this article is copied from Wikipedia, without any attribution given, a link to its source, and generally violates the GFDL in several ways. This includes the image as well.

Posted by: Wolfy at July 13, 2007 1:55 AM

I believe to be into pegging that you would feel the need to do it. It's what is in the heart. I definitely know what is deep inside my aorta. Do it for the need not the want! Gotta love all the way. Lucky you Jenny keep up the wonderful work.

Posted by: Sharon Gayle at August 25, 2007 2:42 AM

Just found this post. You go, girl!

To answer Wolfy, here is the link to the Wiki article: http://en.wikipedia.org/wiki/Pegging_%28sexual_practice%29

The photo of Bend Over Boyfriend there is used by permission of Fatale Media, the producers of the DVD:
http://www.fatalemedia.com/videos/bend_over_boyfriend.html

Lots to learn!

Posted by: Christi Cassidy at August 30, 2007 7:22 PM

Awesome post! Thanks so much for writing about this. Pegging is one of my favorite topics - if only we could more people to do it.

I just learned the other day that one of the couples in the original bend over boyfriend movie is a lesbian and a gay man.. ahh, porn acting!

Posted by: dallas at February 10, 2008 10:25 AM