Rhelyn Harder
- This is the term used when a woman anally penetrates a man while wearing a strap-on dildo.
- Usually it is the woman who initiates it; that’s according to men who have their first time being pegged.
- There was a stigma that anal penetration was equating to homosexuality, which is why most straight men never talk about pegging with their male friends.
There is always a first time for everything. Can you still remember your first kiss, first love or first sex? How about asking a man about his first experience of pegging?
Pretty sure he still remembers it clearly.
Nearly two decades ago by the readers of ‘Savage Love,’ they have coined the word Pegging. This is the term used when a woman anally penetrates a man while wearing a strap-on dildo. Before the 2000s, pegging is an anal play for men was still considered something strictly for queers and straps-ons are unavailable in sex shops.
Pegging was a reference in an episode of TV show ‘Weeds’ in 2006 and was discussed in the raunchy Canadian comedy ‘Young People Fucking’ in 2008. Then slowly pegging started to enter the mainstream. Dan Savage in his weekly column, he answers hundreds of questions from men and women interested in experiencing it.
In 2015, on one of the episodes of ‘Broad City,’ Abbi is asked by her crush Jeremy to peg him. She calls her friend Ilana for advice because she was freaking out, then she puts on the strap-on dildo and penetrates Jeremy. Because of this episode several men spoke to when they put a call out for straight men in Toronto who’d been pegged
.With the agreement to hide their identity, they have shared their first experience being pegged and shared why they thought more straight guy should try it.
Here’s the inside story on the agony and ecstasy of pegging:
What! In My Butt?
Erick remembers in the late 90’s watching the ‘Sunday Night Sex Show’ hosted by Toronto sex educator Sue Johanson on TV. “She was right to the point about anal pleasure for men. It wasn’t gay or straight – just a thing that felt good,” he recalls.
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So he began experimenting on himself, starting with fingers and then one time using a pen. “It didn’t go far, but it felt good,” he says.
In his late 20s he met a partner who wanted to penetrate him anally and usually it is the woman who initiated it as we spoke to men who have their first time they were pegged. Before buying a dildo and harness, Erick’s partner used her finger and tongue.
“It was interesting for me to see how attractive she was with a dildo as a cock. It definitely put into perspective some questions about my sexuality. The only disappointment is we couldn’t find a position that worked well for us comfortably. I’m a bit taller, so our backup plan was always hands and other ways,” says Erick.
Now in his 40s, he was looking for a partner who’d be open to peg him. He considers himself to be straight and had interest from some women but hasn’t met anyone yet who sparked a real connection.
Slowly, Softly Peg Me.
It was in 2014 when Robert was pegged for the first time when he met an older, married woman on a dating site. The woman was very experienced and sexually adventurous with a high sex drive according to him.
“Pegging was a bucket-list item for her and she was willing to be very discreet. She really liked my butt a lot and wanted to spend a good half-hour with it, ” Robert recalls.
Robert thought it was a mistake, but after seeing the pegging episode on ‘Broad City,’ he decided to watch porn to learn more about it because it was all about humiliating the guy and that’s not what he wanted. But then her partner reassured him that his experience would be the opposite. She started by pleasuring his anus orally and digitally before building up to pegging him by using a lot of lubricant she goes slowly and asked for feedback. That experience changed his views how he had sex with female partners.
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“As a guy, you’re ready to go all the time, but when you give your trust to another person, it puts you in a different frame of mind,” he explains. “Being on the other end really gives you more of an appreciation for preparation and that sense of responsibility.”
With his present partner, before bring up pegging Robert waited a few months and he was thrilled to find out that she was into it. She purchased a strap-on and dildo with an additional vibrator that virginally penetrates her, so they’re both aroused during the act.
It’s All about the Butt.
The co-owner of BDSM-focused sex shop Kink Toronto (at 975 Bloor West), Andy Prosserman, says butt-play is having a moment. “People are more open to it. Over the holidays, anal stuff, strap-ons and harnesses were really popular,” he says.
Kink sells assorted butt plugs and trainer kits that are made from silicone, glass or steel which is safe for the body. From their local leather company Aslan, they also offer harnesses and dildos that fit into them. Workshops on pegging are highly popular and participated by group of diverse genders, sexuality and levels of experiences.
“A lot of couples come together to learn because most people are curious about it, but don’t know where to start,” Prosserman had its pegging workshop at Kink is on February 24.
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NOW interviewed David, as one of the most experienced men in pegging wishing that there had been pegging workshop and sex stores selling straps-ons when he was doing it 20 years ago. “In my teens and early 20s, there was less information out there. Internet porn wasn’t even a thing, so I spent years slowly feeling that stuff out on my own and with my partners,” David says.
David is a bisexual and has been open about being anally penetrated by men but he also experienced being pegged by half a dozen of women and the majority of his female have put something up his butt.
“Women bring it up because they know it’s part of my sexuality so they assume it’s on the table,” he explains. “I was never shy about being bi, so the idea that being pegged would make me ‘more gay’ wasn’t a problem.”
There was a stigma that anal penetration was equated to homosexuality, which is why most straight men never talk about pegging with their males friends.
“I was afraid I’d be looked at differently, but I’ve grown out of that,” Robert says. “I’ve asked myself if I feel less masculine by doing it, and the answer is no.”
David agrees. That understanding about anal sex is healthy for everyone. “If a guy is really focused on having anal sex with a woman as a top, he almost owes it to them to try the opposite. Give it up yourself and you might learn how to do it better.”
