The children Bassam Darwich paid for sex were pimped to him by two women who targeted vulnerable young runaways or those in the care of community services.
One girl was 12 when she met him at a hotel in 2011. She shut her eyes and put a pillow over her face when he tried to kiss her.
"It made me feel sick," she told a court.
Darwich, 57, was jailed for at least 20 months in the NSW District Court in Sydney on Thursday for engaging three child prostitutes aged between 12 and 16 on infrequent occasions between 2010 and 2011.
Judge Paul Conlon said the 12-year-old victim had just run away from a refuge when the two women gave her a place to stay.
The girl agreed to sell herself when they told her she'd have to go home if she didn't.
Darwich paid the girl $100 and she gave it to one of the women because she knew she would be asked for it anyway, the court heard.
The judge said another girl was 15 or 16 and a regular user of the drug ice when she moved in with the women.
She initially said she didn't want to have sex for money but ended up agreeing just to keep the women happy.
She said she kept her eyes closed the entire time she was with Darwich and she believes he later paid one of the women about $50, the court heard.
Darwich has denied knowing the girls were so young but Judge Conlon said while the 12-year-old did look older, she didn't appear to be anywhere near 18.
Another girl's concerned mother had shown up at a hotel where her daughter was with Darwich, the court heard. However he simply engaged in sexual acts with her after she left.
Judge Conlon said Darwich's offences had a psychological impact on his victims damaging to their self-worth.
Yet he agreed he didn't mistreat, coerce or exhibit degrading behaviour towards the girls.
He said it was usually argued a person could not be rehabilitated if they continued to deny their offences but in this case he felt Darwich's denial had more to do with embarrassment and humiliation.
He was unable to admit to his family that he knew the girls were underage, Judge Conlon said.
Darwich's sentence has been backdated to May 2017 and he will be eligible for parole in January 2019.