WARNING: Adult themes and graphic details to follow
Asking about anyone's "first time" is always a bit of a can-of-worms situation but, as usual, the Moonman managed to go one further and surprise us all.
As Robin brought up the topic of losing one's virginity, Mooney confessed that the first person he ever had sex with was a prostitute - who was dressed in a country and western get-up.
"I was 19 and I was getting sick of lying about having sex to my mates," Mooney said on Wednesday's The Big Breakfast with Marto, Robin and the Moonman.
"I went with a bunch of mates after being rejected at a nightclub for the umpteenth time. We went to a brothel in St Kilda.
Mooney continued: "I remember it quite fondly. The woman clearly knew I had no idea.
"But she was dressed as a country and western singer. I can't drive through Tamworth with getting an erection!"
Listen to Mooney's heartwarming tale below: