Ian "Clisso" Clissold, 60, has been held at Silverwater jail since February when he was arrested and charged with several domestic violence and child sexual abuse-related allegations.
A 29-year-old woman reported being sexually assaulted by the former Comanchero sergeant-at-arms between 2017 and 2021, sparking a police investigation in October last year.
During the investigation, detectives spoke to another woman, aged 27, about two alleged incidents from May 2017 and June 2020.
On Monday, police charged Clissold with aggravated sexual assault, two counts of aggravated breaking and entering, and attempting to cause grievous bodily harm.
Police allege Clissold sexually assaulted the woman in May 2017 and physically assaulted her in June 2020 during a break-in at her home.
The 60-year-old is already facing allegations that he groomed and sexually abused a girl when she was aged between nine and 13.
He is also accused of the domestic violence-related assault of a 39-year-old woman.
Clissold is due to appear in Penrith Local Court on Tuesday.
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