Diddy was described in federal court Monday (May 12) as orchestrating a string of sexually explicit encounters involving male dancers, baby oil and degrading acts toward Cassie during the first day of testimony in his sex trafficking trial.

One wild moment came when male dancer Daniel Phillip testified that Diddy once tried to direct him and Cassie to act out an “airport fantasy” role play.

“One time, he tried to have us role-play, like we had just met at an airport. We weren’t good, so we skipped that,” Phillip said under oath.

Phillip, who was called to testify by Assistant U.S. Attorney Maurene Comey, said he was first hired to perform at a bachelorette party at the Gramercy Park Hotel.

He expected to dance, but the night quickly turned into something else.

“She was in the hotel room in a red wig, stockings and sunglasses. She gave me a few hundred dollars,” Phillip said, referring to Cassie. “There was a man on the right side of the room.”

That man, he said, was Diddy, wearing a white robe, a bandanna over his face and a baseball cap. “From his voice, I recognized him as Sean Combs,” Phillip said.

Phillip said Cassie paid him for sex while Diddy watched. Afterward, she handed him “a couple of thousand dollars more.”

Over time, Phillip said he was summoned to multiple locations, including Diddy’s Essex House residence and Cassie’s West End Avenue apartment.

The dancer described repeated sexual encounters, often involving excessive use of lubricant.

“How often did you use baby oil?” Comey asked.

“Every time,” Phillip replied. “Sean Combs said we didn’t have enough baby oil on. He’d say, y’all slow down, separate from each other.”

Phillip also testified that Diddy directed him to urinate on Cassie.

“How many times, if any, were you told to urinate on Ms. Ventura?” Comey asked. “They told me not to do it all at once,” Phillip said. The defense objected, but the judge allowed the testimony.

He also recalled being recorded by “Mr. Combs, with cell phone and camcorder. He took a photo of my driver’s license, for insurance,” Phillip said.

When asked what he understood that to mean, Phillip responded, “He was threatening me.”

Phillip said he was once offered drugs by Diddy. He described a moment when he arrived and found Cassie “slumped over.”

Diddy told him, “It’s not going to happen this time.” The dancer also recounted witnessing violence.

“After I saw Sean Combs hit Cassie, I couldn’t do it anymore,” he said. He described Diddy yelling, “B#### when I tell you come over, you come over.”

When asked if he intervened, Phillip said “no,” because of Diddy’s imposing bodyguards.

Phillip said he eventually stopped participating. “I couldn’t do it anymore,” he said. “But I never asked for money. I was happy to get involved with people with such notoriety.”

Diddy, 55, has pleaded not guilty to charges including sex trafficking, racketeering and transporting individuals for prostitution. He faces 15 years to life if he is convicted.

Diddy faced explosive allegations of sex trafficking and racketeering in a packed federal courtroom Monday as his defense attorney pushed back hard against the government’s claims, arguing the Hip-Hop mogul’s relationships were messy but mutual.

Attorney Teny Geragos told jurors that the women accusing Diddy of abuse were not victims of a criminal enterprise but adults who made their own choices in emotionally charged, sometimes volatile relationships.

“Sean Combs had a bit of a different sex life,” Geragos said during opening statements. “The alleged victims were all getting something from him. They are adults. They too must take on responsibility for their lives, as he does for his. A free choice has pros and cons.”

Diddy is facing five federal charges, including sex trafficking, racketeering and transporting individuals across state lines for prostitution.

He has pleaded not guilty and remains in custody following his arrest in September 2024.

Prosecutors allege Diddy used his fame and fortune to manipulate and exploit women for over two decades, citing incidents dating back to the 1990s involving blackmail, violence and coercion.

They claim he led a criminal network through his businesses and employees to facilitate and conceal crimes, including forced labor, kidnapping and obstruction of justice.

But Geragos painted a different picture, focusing on Diddy’s long-term relationships with women like Cassie Ventura and the late Kim Porter, arguing that jealousy, infidelity and substance use—not criminal intent—fueled the drama.

“They remained in multi-year relationships with him. These women were in love with him. Infidelity and jealousy drove the violence. Alcohol and drugs drove things. But he is not a racketeer,” Geragos said. “This case is about his relationships with Cassie and Jane.”

Jurors are expected to see hotel surveillance footage from 2016 showing Diddy allegedly assaulting Cassie. Geragos acknowledged the video but insisted it doesn’t prove sex trafficking.

“The video is not evidence of sex trafficking,” she said. “Cassie walked out of the hotel room with two bags. Combs comes down wearing only a towel. He stomps her and drags her by her hoodie. He comes back around—to get a phone.”

Geragos emphasized that Cassie stayed with Diddy for two more years after the incident, even flying to Georgia in 2018 to support him after Porter’s death from pneumonia.

“She wanted to be Combs’ wife, the love of his life. She spent 11 years trying to get that,” Geragos said. “Cassie had a choice every single day to stay with him. That was her better choice. Until she broke up with him. She was not coerced.”

Geragos also addressed Diddy’s relationship with “Jane,” another accuser, saying she willingly participated in their sexual encounters and continued to see him even after their relationship soured.

“In 2020, with Jane, Combs was more upfront. He told her he was dating other women. She was still jealous,” Geragos said. “Jane did it for the cuddle. She wanted to make him happy. She was unable to resist him emotionally.”

Geragos told jurors they would hear about swinger parties and sexual preferences that may make them uncomfortable, but warned them not to confuse lifestyle with criminal behavior.

“You may not like that. But you are not here to judge him for his sexual preferences,” she said.

The trial, which began May 12, is expected to last up to two months and will feature testimony from multiple accusers and former employees.