“She really liked my butt a lot and wanted to spend a good half-hour with it.” “Pegging was a bucket-list item for her and she was willing to be very discreet,” Robert recalls. She was sexually adventurous with a high sex drive, and according to Robert, very experienced.
Robert was pegged for the first time in 2014, when he met an older, married woman on a dating site. For now, he’s doing what any other guy would do: wearing butt plugs. He’s had interest from some women, but hasn’t met anyone yet who sparked a real connection.
Now in his 40s, he’s been trying to find a partner who’d be open to pegging him, going so far as explicitly stating that desire on his -OkCupid dating profile. I’m a bit taller, so our backup plan was always hands and other ways.”Įrik considers himself to be straight, although he’s open to exploring kinks and has tried painting his toenails. “The only disappointment is we couldn’t find a position that worked well for us comfortably. It definitely put into perspective some questions about my sexuality,” Erik says. “It was interesting for me to see how attractive she was with a dildo as a cock. Almost all the men we spoke to said the first time they were pegged, it was the woman who initiated it.Įrik’s partner used her fingers and tongue a couple times before buying a dildo and harness. It wasn’t until Erik was in his late 20s that he met a partner who wanted to penetrate him anally. “It didn’t go far, but it felt good,” he says. That piqued his interest, so he began experimenting on himself, starting with fingers and then one time using a pen. It wasn’t gay or straight – just a thing that felt good,” he recalls. “She was right to the point about anal pleasure for men.
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Like many Canadians, Erik remembers watching the Sunday Night Sex Show hosted by Toronto sex educator Sue Johanson on TV in the late 90s. So strap yourselves in: here’s the inside story on the agony and ecstasy of pegging. With agreement of anonymity, they told us about their first encounters, what they liked and didn’t like, what made them want to try it and why they think more straight men should experience it.
This episode was referenced by several of the men NOW spoke to when we put a call out for straight men in Toronto who’d been pegged. She freaks out at first and calls her friend Ilana for advice, then ultimately puts on the strap-on dildo and penetrates Jeremy. Then in 2015, on a now-infamous episode of Broad City, Abbi is asked by her crush Jeremy to peg him. Pegging was referenced in an episode of TV show Weeds in 2006 and was discussed in the raunchy Canadian comedy Young People Fucking in 2008. Dan Savage answered hundreds of questions in his weekly column from men and women interested in trying it. Before the 2000s, anal play for men was still considered something strictly for queers, and strap-ons (harnesses with dildos) weren’t readily available in sex shops.īut then gradually, pegging started to enter the mainstream. Pegging, the term for when a woman anally penetrates a man while wearing a strap-on, was coined by Savage Love readers nearly two decades ago. Ask any man about the first time he was pegged, and that memory is usually pretty clear, too. You always remember your first time – whether it’s your first kiss, first love or first time having sex.