The question of whether any part of his behavior with these women was consensual or coerced was the subject of intense questioning over a period of four days in 2005 and 2006, while Cosby, 78, was being deposed in a lawsuit brought by a former Temple University employee.
The previously unreleased documents, obtained by The New York Times, provide an array of information from Cosby on how he said he met and then was intimate with various women over a period of years. He also admitted to having seven prescriptions for Quaaludes in the 1970s.
The documents also make clear that Cosby's wife, Camille, became aware of at least one affair by 1997, according to the Times.
The plaintiff in that 2005 suit, Andrea Constand, accused Cosby of drugging and then molesting her. Several dozen other women have come forward since 2014, accelerating public accusations against Cosby that began several years ago.
Cosby has maintained all he gave Constand during the encounter in question was Benadryl.
Cosby has not been charged with sexual assault and his lawyer has previously called the accusations "utter nonsense." His lawyer did not immediately respond to PEOPLE's request for comment on the newly released deposition.
At one point in the deposition, Cosby explained in more detail how he knew his sexual relationship with Constand was consensual, highlighting one example:
"I walk her out. She does not look angry. She does not say to me, 'Don’t ever do that again.' She doesn’t walk out with an attitude of a huff – because I think that I’m a pretty decent reader of people and their emotions in these romantic sexual things, whatever you want to call them," Cosby said in the deposition, according to the Times.
Constand's suit against Cosby was settled for undisclosed terms; and some documents from the deposition were then sealed under confidentiality and only recently made available. His lawyer had previously argued that releasing the documents would be "terribly embarrassing" for Cosby.
The full deposition is publicly available according to the Times, who discovered it.
Bill Cosby Admits to Drugging Women to Have Sex with Them
"I think you're making light of a very serious situation," Constand's attrorney said to Cosby on the first day of questioning, according to the Times.
He replied, "That may very well be."
Cosby admitted in the deposition to wooing and – he said – sometimes mentoring women during extramarital affairs, such as Constand. He admitted to at least five different sexual relationships, according to the Times.
He spoke about model Beth Ferrier, who he met in the '80s, and how they talked about her career and her father, who had just died.
"Did you ask her those questions because you wanted to have sexual contact with her?" Constand's lawyer asked.
"Yes," Cosby said.
In 2006, Ferrier told PEOPLE that she believed Cosby had slipped something into her cappuccino. In 2014, she said that she had lost "everything" after going public with her story. Ferrier has said that she and Cosby were in a consensual relationship for months in the '80s.
Cosby also admitted to giving women Quaaludes – but always consensually, "the same as a person would say have a drink."
But asked if one woman, who he said he had sex with in 1976 after giving her Quaaludes, was able to consent to their encounter that night while on drugs, Cosby said, "I don't know."