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Bend Over Boyfriend

Dirk Diggler

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.


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