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“I was shocked when my boyfriend asked me to peg him, and even more shocked when I enjoyed it”

Each week, Saoirse Hammond sits down with someone whose story challenges expectations, celebrates individuality or offers a fresh perspective on intimacy, dating and relationships. Between Us replaces judgement with curiosity, proving that the most compelling stories are rarely about shock value - they're about people brave enough to do things their own way.
Man and woman with a bottle of prosecco.
A bit of fun?! Pic: Getty

*Names have been changed for anonymity purposes.*

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It’s a funny thing to feel so strongly for or against something that your views on it become a part of who you are. In my case, I consider myself pretty open-minded when it comes to the world of sex and relationships. I’m no sex guru, but I am the person my friends come to for advice, and that’s got to mean something, right? Wrong.

Writing this column is teaching me that on a scale of vanilla to spicy, I’m a glass of water.

My friends’ stories never fazed me because they were simply not that wild; aside from the odd threesome, our sex lives had been pretty monotonous. The intrigue in our sex stories is usually a result of the new person it’s with, not the act itself.

That all changed when I made friends with someone outside of my usual posse. Let’s call her Molly*.

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Having known Molly for the better half of a year and opening up about everything from exes to family trauma, you get the gist; you can imagine my surprise when she casually dropped into conversation that she pegged her ex.

6’2 and seeking strap-on fun

“WHAT!” I yelped, trying not to choke on my drink.

“Oh yeah, did I never tell you that?” she replied—as if the concept of my friend wearing a strap-on and f*cking her ex would have slipped my mind!

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Demanding more details, I wiped everything we had to discuss from our non-existent meet-up agenda and let her take the floor.

“So yeah, the boyfriend I had in Uni asked me to peg him,” she told me. “It seemed very off-brand for him; he was a 6’2″ landscaper obsessed with the lads, beer and hating on women.” Ah yes, that guy.

“In a funny way, it was actually me who brought it up,” she laughed. “I came across an IGA bag in his bottom drawer while looking for an iPhone charger, and unthinkingly asked, ‘What’s in that?’”

Two models embracing on a beach.
Growing closer and closer. Pic: Getty
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A bag of butt plugs

He clasped his hands, took a deep breath and told her, “Look, this is something I’ve kept deep in the vault. Only my ex-girlfriend knows about this.”

Equal parts panicked and intrigued, Molly encouraged him to go on.

“The bag is filled with butt plugs and a strap-on dildo”, he blurted out. “Oh,” was all Molly could muster as a reply.

“Yeah, me and my ex had an arrangement; she would only let me put it up her ass if she could do it to me,” he explained. “And I ended up actually liking it, but I’m not gay, I swear.”

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‘It made me respect him more’

In disbelief, Molly sat with the news and, for the first time, truly understood the duality of man. “On one hand, he was this toxic tradie with a horrible group of friends,” she told me. “But on the other hand, there he was sitting in his vulnerability with me.”

Recalling how she felt towards him in that moment, she said: “It made me respect him more; I felt honoured that he trusted me with his ‘secret.’”

Shyly asking Molly if she would be open to exploring pegging, her response instantly put him at ease: “Sure, why not?”

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Handing her the IGA bag, he sat back and watched as she inspected the black butt plug, blue dildo and strap-on inside. “The dildo was absolutely massive,” she told me. “Way bigger than his own d*ck.”

Interesting.

One week later, and in the heat of the moment, Molly’s ex asked while still inside her: “Did you want to try that now?”

“Sure,” she replied.

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A woman modelling underwear under a spotlight.
It’s showtime! Pic: Getty

Bend and… peg?

Stepping into the dildo’s harness, she was shocked by the feelings that overcame her. “I felt something I had never felt before during sex,” she said. “In control.”

Loving the feeling of being the one with all the power, Molly couldn’t help but think, “Is this how all men feel?”

Bending her toxic boyfriend over and watching him assume the submissive role for once felt more satisfying than expected. “I won’t go into the gory details, but there was quite a ‘mess’ after the first time,” she revealed.

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Taking the strap-on off, their roles immediately reversed back to normal. “I told him I would throw the blankets into the wash so he could go straight into the shower,” she said. A kindness that, by all accounts, he never showed her.

She pegged him just once more in the following six months they dated. “I’m sure we would have done it more, but he moved back in with his parents,” she laughed. Good to see not much has changed in the past nine years.

‘The most honest he had ever been with me’

“Looking back on the relationship,” Molly trailed away. “His revelation was probably my favourite part; it was the most honest he had ever been with me.”

I think there’s something comforting in the idea that things are rarely as big a deal as they seem.

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As humans, we tend to catastrophise, imagining the worst long before anything has actually happened. Intrusive thoughts convince us that if the people we love discover the “truth” about us, they’ll leave.

But more often than not, the opposite is true. People crave genuine connection, and openness and honesty are some of the most sure-fire ways to create it.

Take the opportunity to build upon your relationship because as the saying goes, “Those who mind don’t matter, and those who matter don’t mind.”

Read more columns in the Between Us series, here.

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