Officials said 33-year-old Joshua Henderson, of Brooklyn, faces rape and burglary charges in the brutal attack.
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Henderson's accused of dressing up as a construction worker -- with a hard hat, reflective vest, and work boots -- and knocking on the door of the victim's Howard Beach home around 5 p.m. Monday.
He allegedly told the woman that there was work being done on the roof and told her to close the curtains. Police said he then climbed into the woman's bedroom window, and when she walked into the room, told her to drop her cell phone.
Telling the victim he had a gun, Henderson allegedly tied up both the woman and her son and then grabbed jewelry, cash and other items from the residence.
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Officials said he then allegedly told the woman she had three choices: "I can choke you and kill you with this pillow, you can have sex with me or I will force you to have sex with your son."
Henderson recently paroled after spending 12 years in prison for burglary. He's been arrested twice since then.
NYPD Chief of Detectives Dermot Shea called this a "troubling incident" and said it brings up a greater issue.
"This case highlights a fundamental breakdown ... how do you have an individual that's paroled for burglaries, and a short time after, within a month or two, caught with the proceeds of a burglary and he's not violated?" he said.
Shea said he's concerned with New York State's sweeping criminal justice reform that passed earlier this year.
Under the new legislation, which will go into effect in January 2020, cash bail will be limited.
Henderson faces up to 25 years in prison if convicted.
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