You always remember your first time – whether it’s your first kiss, first love or first time having sex. Ask any man about the first time he was pegged, and that memory is usually pretty clear, too. After all, it’s a highly sensitive area.

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. 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.

But then gradually, pegging started to enter the mainstream. Dan Savage answered hundreds of questions in his weekly column from men and women interested in trying it. 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.

Then in 2015, on a now-infamous episode of Broad City, Abbi is asked by her crush Jeremy to peg him. She freaks out at first and calls her friend Ilana for advice, then ultimately puts on the strap-on dildo and penetrates Jeremy. 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.

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.

So strap yourselves in: here’s the inside story on the agony and ecstasy of pegging.

What what (in the butt)

Like many Canadians, Erik remembers watching the Sunday Night Sex Show hosted by Toronto sex educator Sue Johanson on TV in the late 90s. “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.

That piqued his interest, 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.

It wasn’t until Erik was in his late 20s that he met a partner who wanted to penetrate him anally. Almost all the men we spoke to said the first time they were pegged, it was the woman who initiated it.

Erik’s partner used her fingers and tongue a couple times before buying a dildo and harness.

“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,” Erik says. “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.”

Erik considers himself to be straight, although he’s open to exploring kinks and has tried painting his toenails. 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. He’s had interest from some women, but hasn’t met anyone yet who sparked a real connection. For now, he’s doing what any other guy would do: wearing butt plugs.

Peg me gently

Robert was pegged for the first time in 2014, when he met an older, married woman on a dating site. She was sexually adventurous with a high sex drive, and according to Robert, very experienced.

“Pegging was a bucket-list item for her and she was willing to be very discreet,” Robert recalls. “She really liked my butt a lot and wanted to spend a good half-hour with it.”

Robert had seen the pegging episode on Broad City, but decided to watch porn to learn more about it, “which was a terrible mistake because it was all about humiliating the guy, and that’s not what I wanted at all.”

When he told his partner, she reassured him that his experience would be the opposite. She started by pleasuring his anus orally and digitally before building up to pegging, using lots of lubrication, going slowly and asking for feedback.

That experience shifted Robert’s views on how he had sex with female partners.

“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 current partner, Robert waited a few months before bringing up pegging and was thrilled to find she was into it. She purchased a strap-on and dildo with an additional vibrator that vaginally penetrates her, so they’re both stimulated during the act.

Butts – so hot right now

Andy Prosserman, the co-owner of BDSM-focused sex shop Kink Toronto (975 Bloor West), says butt-play is having a moment.

“People are more open to it,” he says. “Over the holidays, anal stuff, strap-ons and harnesses were really popular.”

Kink sells a variety of butt plugs and trainer kits (packs of progressively larger plugs) that are all body-safe, meaning they’re made from silicone, glass or steel. They also offer harnesses made by local leather company Aslan, and dildos that fit into them. Their workshops on pegging are highly popular and are attended by folks of diverse genders, sexualities and levels of experience.

“A lot of couples come together to learn because most people are curious about it, but don’t know where to start,” Prosserman adds. (The next pegging workshop at Kink is on February 24.)

David, one of the most experienced men NOW interviewed, says he wishes there had been pegging workshops and sex stores selling strap-ons when he started doing it 20 years ago.

“In my teens and early 20s, there was a lot 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.

He’s been pegged by half a dozen women, but adds that the majority of his female partners have put something up his butt. Part of that is because David is bisexual and has been open about being anally penetrated by men.

“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.”

Fear of anal penetration equating to homosexuality was a stigma we heard across the board, and the main reason why most straight men never talk about pegging with their male 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. He says having an understanding of top and bottom dynamics beyond anal sex is healthy for everyone, and that occupying certain roles during sex doesn’t change your sexuality.

“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,” says David. “Give it up yourself and you might learn how to do it better.”

Anal Bead stem vase by Pansy Ass Ceramics.

The art of Pansy Ass Ceramics

The artwork for this year’s Love & Sex issue is courtesy of Toronto-based duo Kris Aaron and Andrew Walker, aka Pansy Ass Ceramics. Their kitschy and X-rated tchotchkes exploring gay male identity and sexuality became a sensation online a couple years ago. They’ve since moved from Instagram into the gallery world, attracting collectors like Fever Ray, Amy Sedaris and Elton John and exhibiting across North America. Their work is currently on display at the Art Gym Denver as part of the group show Sexxxhibition and their Pansyland exhibition opens at Superfine! Art Fair in Los Angeles on February 14. Check out more work at pansyassceramics.bigcartel.com.

@michdas