Police allege John Miller Elliott, 47, repeatedly asked the woman intrusive questions about the size of her breasts, told her he slept naked, hugged her and said he planned to think about her when he was masturbating.

She was eventually extricated from the situation by a female motorist who witnessed the woman's discomfort and pulled over to assist her.

The alleged victim later told police the encounter left her feeling "terrified, disgusted and sick in the stomach".

The court heard Elliott was already on bail for two separate incidents - one of which stemmed from allegations he was caught masturbating inside a clothing boutique in May - when he began following the alleged victim after she got off a train on Monday morning.

He allegedly closed in on her on Park Street and told her "I'm not wearing any underwear, I sleep naked. I used to be a body builder".

The woman told police she tried to deflect his comments but he persisted and continued to stand in close proximity to her.

"Do your boobs get in the way when you sleep?" Elliott allegedly asked the woman, also inquiring about their size and whether she put them in her mouth to "measure them".

Elliot also allegedly spoke to the woman about his penis in explicit detail, his intentions to go home and "touch myself to my thoughts and images of you" and at one stage asked to hug her, which the woman reluctantly agreed to in a hope it would make Elliott leave her alone.

Meanwhile, the driver managed to get a picture of Elliott and waited until he left the scene. She then took the alleged victim to Wollongong Police Station where the two provided statements.

Elliott was arrested on Monday afternoon and charged with common assault and intimidation.

In court on Tuesday, defence lawyer Jordon Mechan said Elliott believed he was being "unfairly targetted" on social media, including being called a "paedophile" on Facebook and was living in fear.

"People are well aware of him and his court cases and are targetting him," Mr Mechan said.

"He denies all the allegations quite vehemently. He's fighting all the charges before the court."

Mr Mechan said Elliott had been diagnosed with a personality disorder and had never spent time behind bars before.

He suggested Elliott was unlikely to receive a full-time custodial sentence if convicted of the current charges.

He applied for bail on Elliott's behalf, saying he would agree to abide by any conditions imposed by the court.

However, Magistrate David Degnan refused to release Elliott, noting he had previous convictions for obscene exposure and indecent assault.

"The allegations before me certainly are concerning," he said.

"He [is accused of] pursuing, intimidating and assaulting a lady. He followed her from Woonona Railway Station and engaged her in completely inappropriate conversation."

Magistrate Degnan said the case against Elliott appeared a strong one.

Elliott will remain behind bars until his next court appearance in October.