Brian Jeffrey 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, prosecutors say. The images date to 2006 and track much of Raymond’s career, with victims in Mexico, Peru and other countries.

The case was just the latest embarrassment for the CIA, which in recent months has seen a reckoning over its often secretive and antiquated handling of sexual misconduct claims within the spy agency.

The Associated Press found at least two-dozen women have come forward to tell authorities and Congress about sexual assaults, unwanted touching and what they contend are the CIA’s efforts to silence them. A CIA officer trainee was convicted in August of assault and battery for wrapping a scarf around a colleague’s neck and trying to kiss her inside a stairwell at the agency’s headquarters in Langley, Va.

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.

Investigators combing his devices found an incriminating online search history for phrases such as “Ambien and alcohol and pass out” and “vodka & valium.” In one email to an online pharmacy, Raymond wrote, “Hello, do you have chloral hydrate for insomnia?”

When he was arrested three years ago, Raymond had been stationed in Mexico City, where he would meet women on dating apps and invite them back to his embassy-leased apartment for drinks.

The San Diego native, who is fluent in Spanish and Mandarin, was only discovered in 2020 after a naked woman Raymond met on Tinder screamed for help from his balcony, prompting a worried neighbor to call the authorities. U.S. officials scoured Raymond’s electronic devices and began identifying the victims, all of whom described experiencing some form of memory loss during their time with him. Prosecutors had intended to call as many as 14 alleged victims during trial.

Raymond withdrew a previous guilty plea in the case last year as he successfully challenged the admissibility of certain photos that the judge ruled were illegally seized from his mobile phones after agents compelled him to give up his passcode. Other images stored on Raymond’s iCloud account were admitted however.

As part of the agreement announced Tuesday, Raymond pleaded guilty to four of 25 criminal counts including sexual abuse, coercion and transportation of obscene material. Prosecutors dismissed the most serious charge of aggravated sexual abuse.