Bend Over Boyfriend
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.
Comments (47)
best. post. ever.
> sex should be done sober.
whoever says this should have their "sexpert" license revoked!
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.
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.
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?
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?
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."
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.
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.
"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?
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.
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.
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!
Gloria: If you read Now you'll see that it is the type of content in that magazine, that's why I said it.
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.
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.
Hey,wait a sec, Im an attractive strait guy and I would love to get pegged its just role play. Any takers? lol
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!!!
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.
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!
According to my coworker, every boy he knows who's done it LOVES it.
I'd definitely give it a try.
OMG... The United Pegging Association (UP-Ass) is on Facebook!
http://www.facebook.com/group.php?gid=3211125011
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.
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.
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!
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!
I'm 37, married twice, and have pegged both my present husband and my ex.If it feels good people will do it. Many guys want to try it but social stigma prevents them.Same with the gals.
I am one of those guys who really enjoys this. Since there are not that many women who do this, I decided that I would do my part to increase the supply. I have taught more than ten women to do this. Only one was not really into it. She would do it for me because she liked me, but it was not really exciting for her. The rest really did enjoy it. In response to your assumption about wanting the real thing. I have been doing this for a few years now. I enjoy giving and receiving anal sex. I am only really attracted to woman. I am not homophobic. There is just not anything there with men. I am probably not alone in this.
To be totally honest I believe myself to be one of the luckiest Men alive. I discovered I liked a dildo in my rear 17 years ago. NO, I am not gay. I found a woman who never had tried anything like that. She was and is quite shy in and around people. But the first time I convinced her to try it, She was getting off the whole idea. We actually got to the point that when on top of her with me riding the strap on, she loved to stroke it, she would have an orgasm doing it. And yes this is the truth, You see, she is a squirter, so she cums from watching me ride it and she strokes until I cum. So, YUP, I am the luckiest man on the planet..Whooo Hooo
I was an 18 yr old virgin when I was first pegged by my 24 year old girlfriend, who had made it a requirement b4 intercourse, without telling me. She had made her interests clear to me on our second date, showing me a magazine with gay men fucking and being fully penetrated by a hand and by objects(billiard balls!). I didn't run away, probably because of her hand on my thigh and her sexiness. She had me undress slowly for her and pose, pulled my underwear into a tight wedgie and had me unveil my massive hard-on, very slowly. She had me stroke myself and not cum until told to, when I exploded and accidentally hit myself in the face with cum and produced a huge pool of cum on my stomach, which she fed to me with both hands. She cleaned me with a warm towel and then had me get on all fours. she had me spread my legs and fondled my balls and my ass until I was rock hard again. She slapped my ass a couple of times, told me I had a great ass and then told me to get dressed. When I couldn't zip my pants up, she laughed and told me to get a glass from the kitchen, had me stroke myself until I came in the glass. She smiled, looked at me and said 'Well, what are you waiting for?' and brought the glass to my lips and tipped it up, filling my mouth with my own cum. I didn't swallow until, a few minutes later, she told me to do so, scraping the glass of the remnants of cum and having me lick her fingers.
We still hadn't kissed and I was still naked and she was fully dressed. She grabbed one of the gay men's magazines and showed me her favourite picture, one of a man being fucked by another man's hand while a group of men and women watched. She then put me over her lap as if to spank me, excused herself, then came back with something in her hand. In the spanking position, she dry shaved my ass, telling me it was my responsibility from now on to keep it completely smooth. She then sent me home and told me to pick her up from work on Friday (this was Tuesday) and not to masturbate. She tied a red ribbon around my hard-on to remind me.
Three months of performing oral on my back and being rewarded with a fabulous blow job when I was good, culminated in me getting a phone call from my girlfriend telling me to strip, get down on all fours with head down, eyes closed and leave the apartment door open, one afternoon. I heard her come in, talking to someone and realized that someone was there with her. Soon, I was being fondled by someone and was barely in control of an imminent orgasm when someone squeezed my balls, hard. I felt something being tied around my balls and was led over to sit on my knees in front of my girlfriend. I was handed a leather device to place around my cock (to stop me from orgasming) and was led into the bedroom on all fours and given some leather handcuffs with a metal ring to put on. One went around my neck and my hands were linked to my neck. Next were my ankles and then a metal rod attached to spread my legs. I was told to try and stand up and I could not. I was helpless.
The stranger then stood in my line of sight. She was a pretty, slight blonde not much older than me. She took off her dress and lay down on the next bed, stretched provocatively, smiled at me, bent over and fondled my cock and complimented me on my 'nice equipment' and told me her name was Marilyn.
She kissed me and we started necking. She told me to relax and keep my eyes on her. My girlfriend was out of sight, behind me and Marilyn said, 'Let's get started' and the whip in my girlfriend's hand whitled through the air and struck my ass. Eleven strokes later, Marilyn wiped my tears and told me that this would happen again if I misbehaved and that I should be proud of the permanent whip marks on my ass. The two women then embraced on the next bed and fondled each other. A few minutes later, Marilyn explained that I was now part of a threesome, with certain unspoken rules. As she said, 'Here is rule 1' I felt a sharp pain in my ass as my girlfriend penetrated me with a small, slightly lubricated 6 inch dildo, and proceeded to fuck me at top speed. Marilyn fucked me next, with an 8 inch, thick, very flexible dildo. The next 3 were 9"(very thick, black, with a bulging head), 11" grey and thinner and a 14" double headed extremely thick black dildo.
Three weeks later, I lay on my back while my girlfriend lowered herself on to my cock. I was not allowed to cum inside her then or now (4 years later) and still have to eat my cum whenever it is produced. I live with my girlfriend and Marilyn and get pegged about twice per week. Gradually, I have been feminized to their tastes, including shaving my body, wearing pantyhose and panties and high heels around the house - and sometimes outside. I have some beautiful wigs and frequently use lipstick and nail polish. My male clothes are dwindling, just enough to go to work now, while my female wardrobe increases regularly. I no longer wear a leather chastity belt as my birthday presents were to have my cock pierced - strategically, Marilyn said - allowing for a beautiful metal, jewelled chastity device, which allows and encourages erections but prevents orgasms - which only happen when both women agree. My girlfriend has openly wondered whether I can tell the difference between a cock and a dildo and Marilyn has told me that they have spoken to a couple of men who are willing to initiate me and see if I can tell the difference, through a reenactment of my pegging initiation, with me blindfolded and ear plugs in, being asked, 'What's in you now, cock or dildo?'. I have been promised safe sex only. If I get the answers right, that is all that is going to happen. Any wrong answer will mean that I will be initiated into performing fellatio until each man is fully satisfied, so Marilyn thinks I may be sucking up to 3 cocks, twice each. Clearly, I'll be taking it in the ass from men on a regular basis from now on as well as sucking cock. Marilyn is looking forward to watching the video of my initiation with me after I get over the fact that I am going to be transformed into a willing, full-time gay transvestite. She thinks I may be able to look forward to a future as a very popular stripper at a gay club and plans to circulate the videos widely, including on the net.
when i came home from work today, I was told to change in to my special party dress, a sexy little pink mini, and wear a blonde wig and full makeup and I am now wearing the clothes and have finished my makeup. Five men are visiting tonight for a demonstration pegging by Marilyn of me with a 9 inch strap-on. my girlfriend told me to be prepared for a profound 'lifestyle change', so I presume that the men are going to play a 'dildo or cock' game with me, but my girlfriend won't confirm it. Marilyn told me that if i 'pass the test' that something extremely intense was going to happen on Halloween. a video camera has been set up, so...
marilyn fucked me with the 9 inch, very sensually and for a very long time and I really loved it. the audience and the tension about what was happening next made it unusually arousing.
i was then restrained as in my intro to pegging, kneeling at the end of the bed with my chest on the bed. i was also blindfolded and had ear plugs, to concentrate my senses in my ass. i was then gently penetrated by what I thought was a small dildo, a fucking that stopped after a few strokes. the ear plugs were removed and I was asked, 'cock or dildo?' and i said 'dildo'. Marilyn leaned over and kissed me on the mouth and said 'wrong - and you know what that means, you get to suck 5 cocks again and again, on camera and compare the taste of their cum to yours!' I had never seen Marilyn, or my girlfriend so happy and triumphant.
My first man then stripped - he had only unzipped to fuck me - slid down in front of me and rubbed his cock slowly all over my face and then told me to lick his balls. he wrapped his legs around my head, rubbing his wet balls and cock all over my face. Then he forced his cock down my throat without warning.
Quite frankly I had enjoyed what was happening up until then, mainly because I was pleasing the 2 women in my life, but i could not control my gag reflex, with unfortuante results, which I will not go into here.
I was spanked, hard by Marilyn and my girlfriend and the 5 men for about 30 minutes. the men then left, but Marilyn told me in no uncertain terms that it was only an adjournment until friday night. Marilyn told me later that a decision had been made to proceed with a Halloween gang bang of me, the 5 men would return and that I would be accommodating a very large number of men in addition to the 5, both with my mouth and my ass. 'My girlfriend explained that after i recovered from being gang banged, many things would happen, but that I would be on call to all of the men who gang banged me, permanently, and that she expected that as soon as they had fully trained me to deep throat, that i would be sucking about 10 men every day.
I can't believe that she really means it, but I am hers to do with as she pleases.
At 47 years old, I was just introduced to pegging this year. Sure I've had vibrators, dildo's and such up my ass, but never had I experienced "Strap-on" sex with a female. Wow, it is incredible!
My lady of 4 years loves it just as much as I do. She loves being in the dominate role and giving me pleasue. She always talks dirty and such while taking me. I am by no means gay and have never fantasized about gay sex, but my lady can stick her dick in me anytime she likes and I'll always want more!
Jay
I've enjoyed anal stimulation for years. Late last year my partner of 10 years discovered one of my toys. At xmas I bought her some toys and a new one for me to introduce mutual toy play to our sex lives. I've left one toy out in my bathroom for her to get use to their existence and slowly have her use them with me. She actually had a harder time of me performing oral acts on her toys then penetrating me with mine, but I explained it is a major turn on to perform a taboo act for her as she watches and she is getting use to it. Next step is to get her harnessed to enable her to truly be able to sodomise me.
This weekend just past was eyes rolling into the back of my head ecstasy...I think it helped when last year, a tv station had a sex show on where one episode was upon male anal stimulation and techniques. Also when she has participated in anal play with me (only a couple of times so far), I have thanked her and snuggled up and reassured her how much I really enjoyed SHARING it with her and how I hope she will keep satisfying me in this way. I've also shown her by performing penetration on myself to help her get use to it over time. At first she was a bit disgusted, but has gotten use to the idea.
After this weekend I am confidant she is completely comfortable with it now, including feeding me her toys, while working my toy upon that magic spot inside me and with my desire to get her a harness to be able to truly fuck my brains out.
I don't have the balls to ask my wife to do it, but I want to be pegged. Whenever I get the chance, I put my wife's vibrator up my ass. It's big - about the size of a cock. My wife is shy and a bit of a prude. Maybe I'll start by getting her drunk and massaging her asshole. Hopefully that will open her up, so to speak.
ive found itharder to feel comfertable telling the girl i like or love that i wanan be pegged and the ones i have told dint like the idea and made me feel weird for even bringing it up so id say its hard both ways
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