Shock Jock Kyle Sandilands shocked at radio co-host Jackie O’s sex confession

Zach Margolius
The Nightly
2 Min Read
Not Supplied
Not Supplied Credit: Supplied

After more than 20 years sharing the airwaves, you’d think shock jocks Kyle Sandilands and Jackie ‘O’ Henderson might’ve squeezed every colourful confession out of each other over the stretch.

Two weeks after launching their breakfast show in Melbourne, the pair told News.com.au a few scandalous stories that had slipped through the cracks.

Tasked with a cheeky game of “Never have I ever (had sex with a celebrity)”, Kyle was the first to disclose his hit list.

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“Models, celebrities, actors, singers, I’ve banged them all,” he boasted.

Kyle and Jackie O have broadcast in Melbourne for the first time. Picture: Instagram
Not Supplied Credit: NCA NewsWire

However, unaware his work wife too had shared her body with a celeb, Kyle was gobsmacked she’d been so tight-lipped about her conquest.

“Who the f**k did you root?” Kyle asked. “Do I know?”

“Maybe I never told you,” Jackie replied coyly.

Blowing off the forthcoming interrogation, the 49-year-old mother told Kyle it wasn’t a famous sportsman or chef.

Married twice before, Jackie openly shares dating stories on the pair’s radio show.

Henderson in 2021 on The Masked Singer.
Henderson in 2021 on The Masked Singer. Credit: Instagram/jackieo_official/jackieo_official

Most commonly meeting potential suitors through mutual friends, Jackie spoke recently about sharing the bedroom with a fan.

“Halfway through sex, he says, ‘I can’t believe I’m having sex with Jackie O’,” she admitted during the broadcast.

While the bronzed blonde suggested she’d prefer to date someone with “nothing to do with the entertainment industry”, Kyle believed he’d narrowed Jackie’s type to a tee.

Or more specifically, “some bussy boy with a moustache that looks amazing in some Billabong boardshorts down at the pub”.

Kyle Sandilands
Kyle Sandilands Credit: Nicholas Wilson

But he didn’t stop at her ideal man’s appearance.

“Jackie thinks broke d**k (poor) men give better sex because they’ve got nothing else going for them,” he said. “A wealthy man in his Audi, he doesn’t know how to please a woman.”

“I never said that,” Jackie responded, but did concede, “Tradies are better than … guys that are killing it in finance”.

Jackie On in a dress of black contrasted with sequins and cut-outs at her midriff.
Jackie On in a dress of black contrasted with sequins and cut-outs at her midriff. Credit: Instagram/jackieo_official

Recalling life as a “cokehead” following his first marriage’s demise, the 52-year-old admitted he “just banged everyone who wanted to be banged”.

“This is going to sound like a lie, but (I had) 15 girls in one room at once and just me… they were really eager to please me,” Kyle insisted.

“I think maybe I had to pull out halfway (through). I thought, ‘I can’t please them all’.”

Not to be outshone, Jackie revealed she once had a sex dream about her co-host before admitting her parents accidentally caught her “self-pleasuring” in the bath in her younger years.

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