Sean "Diddy" Combs' former escort has shed some new light on Cassie Ventura's alleged bans while partying with the music mogul at his "freak off" parties, where she was allegedly ordered to bow to his every sexual demand.
Shawn Dearing, a former escort hired through Cowboys4Angels, shared his experiences on the "Michael &" podcast, claiming Ventura was not allowed to engage in any sexual activity unless Combs was physically present. "There was no interaction without him there," Dearing said, recalling a moment where Ventura, naked and on a couch beside him, abruptly stopped and told him, "Not till he comes back."
The alleged rule, according to Dearing, showed how these events weren't about pleasure but about power. "It was all about power," he said. Prosecutors in Combs' federal trial described the gatherings as highly orchestrated sex shows "elaborate and produced performances" that Combs would direct, film, and sometimes join mid-act.
Escort Says He Was Nearly Present During Cassie Assault
Dearing also revealed he was supposed to be at the Los Angeles hotel the night Combs assaulted Ventura, an incident caught on security video. "I don't know what would have happened," he said, suggesting he might've tried to physically restrain Combs. "I would like to try to tone it down... I would try to bear hug him."
These claims follow Combs' conviction earlier this month on federal charges of transporting women across state lines for prostitution. Though found not guilty on sex trafficking and racketeering conspiracy, the conviction still carries serious sentencing implications.
How Much Time Will Diddy Get?
Legal experts say the sentence could range from time served to 20 years. While both sides agree on a base offense level of 14, the prosecution is pushing for 24, arguing Combs managed a wide criminal operation involving more than six victims.
The defense insists the number should be 16, suggesting a range closer to two years.
Judge Arun Subramanian, who denied Combs' bond due to concerns about his "disregard for the rule of law and a propensity for violence," will make the final decision at sentencing on October 3.
Attorneys following the case expect the sentence to land somewhere between the defense's and prosecution's proposals. "The judge has the discretion to split the baby," said attorney Arick Fudali, per Complex, who represents two of Combs' accusers. "He's weighing not just the guideline range, but the broader threat Combs poses."
Whatever the outcome, Combs' time behind bars could be reduced by federal "good time" credit, meaning even a 36-month sentence might only require another 20 months served, minus the year he's already spent in jail.
Ventura was among the first to file suit against Combs, triggering a cascade of lawsuits and criminal investigations that ultimately led to his conviction.
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