R Kelly pleaded not guilty to 11 additional charges levelled at him in his latest court appearance.
Among the 11 new counts which he denied are four counts of aggravated criminal sexual assault, which carries a sentence of up to 30 years in prison.
That term is more than four times as long as the maximum possible for each of the 10 counts Kelly was originally charged with in February.
Kelly stood with his hands folded in front of him as he listened to Judge Lawrence Flood describe the charges to him.
When asked if he understood, Kelly, responded: "Yes, sir."
The Grammy award-winning singer has denied any wrongdoing.
He left without making further comment and a status hearing was scheduled for June 26.
His defence attorney, Steve Greenberg, said after the hearing that he could not speculate as to why prosecutors brought the new charges.
They pertain to one of the four women he was charged in February with sexually abusing years ago.
Three of his accusers were minors when the alleged abuse occurred.
"It's the same case. It's just that they've just changed what they've charged him with," Mr Greenberg said.
"It's the same facts ... the same bond, the same evidence. We expect the same result."
According to the new indictment, the first eight counts are from encounters that allegedly occurred between January 1 and January 31, 2010.
Three others pertain to alleged encounters between May 1, 2009, and January 31, 2010.
Prosecutors allege that Kelly used force or threatened to do so to pressure the accuser into sex or to perform oral sex on him.
Since she was underage at the time, the statute of limitations for bringing charges was extended to 20 years from her 18th birthday, they wrote.
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