A serial rapist on Sydney's northern beaches who believed "a playful no" did not mean no, has been jailed for at least two years and three months.
Caleb Winter, 24, was sentenced to a maximum term of four years and three months in Sydney's District Court after receiving a 25 per cent discount for his guilty pleas to three counts of having sexual intercourse without consent.
Judge Christopher O'Brien on Friday said Winter overpowered his victims using superior physical strength, and his offending showed an unacceptable sense of entitlement.
The arborist was arrested in February 2021 for the charges against three separate women between 2016 and 2020, according to the facts of the case.
Winter aged 18, met his first victim aged 17 in a spa bath at their mutual friend's home in Dee Why, and when alone pointed to his erect penis poking through the bubbling water.
"Oh look," he said, before grabbing the woman under her bikini.
She soon left the spa and was changing in a bedroom when he entered saying, "you know I'm just mucking around."
He then picked her up, despite her protests of "stop" and "no" and pinned her down and sexually assaulted her before being pushed off.
"It's not a joke when you actually do something like that," she yelled.
Three years later she made a police statement but Winter denied all accusations.
He met his second victim in May 2019 online via Tinder before the pair had consensual sexual intercourse.
After their third date the woman said she was suffering from a vaginal infection, but Winter proceeded to take off his shirt and pants while they were kissing.
She said "no" at least six times, and "I don't want to have sex now".
But he continued to touch all over her body, and sexually assaulted her while saying "you're teasing me" and "you want a little f***".
She yelled '"no Caleb, I can't believe you just did that".
He responded: "I didn't want it anyway, I don't need you, I can just go have a wank". She then drove him to a Beacon Hill home and never saw him again.
After his arrest he told police "if she was crying, yelling or screaming I would stop".
But "if they were saying no in a playful way", that "he could tell the difference".
He explained the pair had previously had sex, and assumed that meant she was consenting again.
"In my eyes I still had permission because she was the same girl."
After meeting up with his third victim in Chatswood the pair returned to her Lindfield home to watch Netflix where he continually put his hands down her pants. She would grab his wrist but he was too strong.
After he sexually assaulted her she said "I am feeling emotional I am going through some stuff, you just don't understand the word no."
They continued watching television and he tried to push her head down on his crotch, but she protested.
"After everything I've done for you," he said.
An expert report found Winter had experienced early developmental issues from a disrupted childhood and a turbulent adolescence.
He experienced periods of homelessness from age 15, and began smoking cannabis and drinking heavily.
A psychologist concluded Winter was suffering long-term depressive symptoms and low self-worth, but had since developed considerable insight into his offending and immaturity.
In a letter to the court Winter said he was truly sorry for the pain and anguish he had caused his victims.
"My mental state at the time was no excuse for the way you were treated and I realise now that my actions were not acceptable."
Judge O'Brien said early emotional abuse had impacted his ability to interpret cues from others in emotionally charged situations, and that he had good prospects of rehabilitation.