Diddy timed his ‘freak off’ orgies with the biggest nights in showbiz, according to videos and documents obtained by the New York Post.

The rapper, real name Sean Combs, held at least three raucous sex parties after major events, the videos reportedly show.

Prosecutors allege that many of the sometimes-days long sessions dubbed ‘freak-offs’ involved women who had been blackmailed or coerced into taking part.

The Post reports it has viewed footage from star-studded after parties hosted by Diddy, following the 2004 and 2005 MTV VMAs in Miami and the 2005 Super Bowl in Jacksonville among others.

One clip taken after Diddy, 54, had hosted the 2005 VMAs reportedly shows the afterparty descend into a wild party, with two men seen having sex with a young girl who had powder under her nose.

In another clip a couple is reportedly seen having sex on a table as other people look on.

The after party was attended by the likes of Eva Longoria, Paris Hilton, Ice-T, Fergie, Quincy Jones and NASCAR  executive Jeff Gordon.

There is no suggestion the celebrities were aware of what the party descended into as they had left before the videos were taken.

However, Diddy is clearly visible the Post reports and is seen sporting the same T-shirt he was photographed in earlier in the night. 

Clips from after Diddy’s post-Super Bowl party in 2005 show similarly debauched scenes unfolding at a $2 million Sawgrass mansion which the rapper is understood to have leased for $20,000 a week.

The footage reportedly shows two men having sex in front of a group of people. The Post says another clip appears to show Diddy filming from his perspective while having sex with a woman.

Earlier in the night, Diddy had rubbed shoulders with the likes of Ashton Kutcher and Ashlee Simpson, although there is no indication they knew what would happen later on or were present for it. 

The behavior apparently on display in the videos echoes claims made by a woman who has filed a lawsuit claiming she was raped when she was just 13 by Diddy  during the 2000 VMAs in New York City.

Combs allegedly ‘aggressively approached’ the young girl with a ‘crazed look in his eyes’ before sexually assaulting her at the event, the legal document seen by DailyMail.com, claims.

She claims an unnamed male celebrity also raped her while Combs and an unnamed female celebrity watched.

The music mogul is was hit with host of sex trafficking and racketeering offenses following his September 16 arrest. Since then, upwards of 120 victims have already come forward.

The criminal indictment was brought after investigators swooped on the rap star’s Miami and LA homes where prosecutors say they found, ‘1,000 bottles’ of baby oil and lubricant allegedly used in the freak offs. 

Diddy maintains his innocence, and will face a jury in the spring.

He is currently being held at at Brooklyn’s notorious Metropolitan Detention Center (MDC) since his arrest after his requests for bail were denied.

If convicted, Diddy could be sentenced to life behind bars.

Larry Levine, director and founder of Wall Street Prison Consultants, appeared on DailyMail.com’s podcast, The Trial of Diddy, where he revealed Combs is getting daily visits from a psych team that’s monitoring his mental health.