A New York man faces more than 200 sex-crime charges after police found videos of him allegedly raping women and hundreds of images of child pornography.

Police believe 31-year-old Cameron McDermott drugged and sexually assaulted two unconscious women in Manhattan apartments, recorded the acts and then stored and meticulously cataloged the recordings, the New York Post reports.

The videos show that he raped one woman eight times in 2010 and a second woman at least five times in 2013, prosecutors said.

McDermott can be seen in the videos “fondling the unconscious women, inserting an object into one’s vagina and sodomizing the other,” the New York Post reports. He would sometimes slap a woman’s face to show that she was unconscious in the videos.

McDermott knew both of the women, but neither were aware of the sexual assaults or of the recordings, according to authorities.

The videos were stored on McDermott’s computer in a very detailed and organized way, Assistant District Attorney Jamie Kleidman said. In one case, there was a folder marked “rape” that contained videos of him raping the women.

“The defendant meticulously recorded each of these actions, and then labeled them on his computer, under files named things like ‘unconscious’ and the victim’s name, a folder marked ‘undressing’ and the victim’s name,” Kleidman said in court on Thursday.

Kleidman also said the child pornography was “meticulously marked by age, like ‘2 years old’ and the actions the children are being forced to engage in, such as ‘daddy and daughter.’”

Police arrested McDermott in January after he allegedly exposed himself multiple times to women on Long Island, the New York Times reports. While investigating that case, a detective searching McDermott’s apartment found the cache of disturbing material on electronic devices.

In one bizarre episode, McDermott allegedly wore a wig, yoga pants and lipstick while exposing himself to a victim and then urinated on her leg, court records show.

McDermott was charged Thursday with upwards of 200 counts of predatory sexual assault, rape, sex abuse and illegal surveillance in connection with the recordings. He appeared in State Supreme Court in Manhattan and pleaded not guilty.

Prosecutors urged a judge to detain McDermott because he comes from a wealthy family and has the means to flee, the Post reported.

While a defense lawyer said McDermott isn’t a flight risk, the judge ordered that he be held without bail.

McDermott could face significant jail time if convicted on the most serious charges.

Feature photo: Garden City Police