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WASHINGTON (NewsNation) — A former CIA officer accused of drugging and sexually assaulting at least two dozen women during various overseas postings pleaded guilty Tuesday in Washington to federal sex abuse charges that could land him behind bars for up to 30 years.

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.

Officials said Raymond admitted to taking pictures and videos of 28 naked and partially naked women without their consent over the course of 14 years.

Raymond was “touching and manipulating the victim’s bodies” in many of the recordings. It continued to say that the women were “unconscious or incapable of consenting,” according to a news release from the U.S. Department of Justice.

Raymond pleaded guilty to four of 25 criminal counts including sexual abuse, coercion and transportation of obscene material. As part of the agreement announced Tuesday, he faces between 24 and 30 years in prison when he is sentenced in September.

The Associated Press and NewsNation affiliate DCNewsNow contributed to this report.