WASHINGTON (WDVM/AP) — A former CIA officer accused of drugging and sexually abusing women in multiple countries pleaded guilty Tuesday to federal charges, according to the U.S. Department of Justice.

Brian Jeffrey Raymond pleaded guilty to four of 25 criminal counts including sexual abuse, coercion and transportation of obscene material.

Prosecutors said Raymond kept nearly 500 videos and photographs he took of naked, unconscious women, including many in which he can be seen opening their eyelids, groping or straddling them. The images date to 2006 and track much of Raymond’s career, with victims in Mexico, Peru and other countries.

The DOJ said that Raymond tried to delete the pictures and videos after learning about the criminal investigation. 

The CIA has publicly condemned Raymond’s crimes, and CIA Director William Burns in May launched a series of reforms to streamline claims, support victims and more quickly discipline those involved in misconduct.

“As this case shows, we are committed to engaging with law enforcement to ensure that justice is served,” the CIA said in a statement. “In addition, we take any allegations of sexual assault or sexual harassment extremely seriously and have taken significant steps to ensure we maintain a safe, inclusive and respectful environment for our workforce.”

Raymond’s defense attorney did not respond to requests for comment.

Prosecutors described the 47-year-old Raymond as an experienced sexual predator who kept a detailed accounting of potential victims organized by name, ethnicity and notes on their physical characteristics.

As part of the agreement announced Tuesday, he faces between 24 and 30 years in prison as well as supervised release for life. He will also have to pay mandatory restitution to the victims.

The Associated Press’ Fu Ting, Jim Mustian and Joshua Goodman contributed to this story.