The defense used the cross-examination of U.S. Attorney's Office Special Agent DeLeassa Penland to present messages in which they contend former Sean Combs girlfriend Cassie Ventura appears enthusiastic about "freak-off" sexual encounters or entices Combs with suggestive talk.

“I bought the sexiest outfits for later,” one message from October 2012 said. “I’ve been really horny,” a message a few months later said.

In another message, from December 2012, Ventura promised “I’ll be the nastiest freak b----.”

Ventura once texted Combs about a role-play game, according to the messages. “The game starts at 10 p.m. no texting after this,” the message said. “I am not Cassie and you are not Sean.”

The defense has argued that Ventura's participation in the sexual encounters that Combs desired was consensual and not coerced, as the prosecution claims. Ventura previously testified that she was an unwilling participant and was texting Combs what she knew he wanted to hear.

On re-direct examination, prosecutor Emily Johnson returned to the caught-on-camera attack on Ventura by Combs at the InterContinental Hotel in Los Angeles, showing the jury a message Combs sent to Ventura five days later, which read “Baby, I can’t say it enough. I AM SO SORRY!!!!!”

The jury saw Ventura’s response. “I still have crazy bruising from Friday,” her reply message said. “Nothing good comes out of ["freak-offs"] anymore. You treat me like Ike Turner.”

Penland is off the witness stand.

Court has adjourned for the day. Testimony will resume Wednesday with former Combs associate Brendan Paul scheduled to take the stand.

With U.S. Attorney's Office Special Agent DeLeassa Penland under cross-examination, the defense played long excerpts of "freak-off" videos that were taken from former Sean Combs girlfriend Cassie Ventura’s laptop.

Combs, jurors and lawyers donned headphones and video monitors in the gallery went dark as the videos were played. For a moment, some of the sound bled through before the courtroom made an adjustment.

It is not clear what the clips showed but they were longer than the brief excerpts the jury saw Monday during direct examination.

Defense attorney Teny Geragos has previously downplayed what’s depicted on the videos.

“These videos, we believe, are powerful evidence that the sexual conduct in this case was consensual and not based on coercion,” Geragos said during her opening statement.

After his 2016 caught-on-camera attack on then-girlfriend Cassie Ventura at InterContinental Hotel in Los Angeles, Sean Combs called and messaged her repeatedly but Ventura-ignored most of the communications, according to phone records introduced at trial.

The jury first saw messages arranging the "freak-off" that Ventura testified preceded the violence that was captured on hotel surveillance footage the jury has repeatedly been shown.

The jury next saw phone records that showed Combs made dozens of unanswered phone calls to Ventura following her departure from the hotel. He also messaged her.

“Call me now,” one message from Combs demanded. “You gonna abandon me all alone,” another message said.

Ventura responded once. “I have a premiere Monday for the biggest thing I have ever done in my life. I have a black eye and a fat lip. You are sick for thinking it’s OK to do what you have done,” her message read. The premiere in question was for the film "The Perfect Match," in which Ventura starred.

Over the next several hours came more unanswered phone calls from Combs to Ventura, according to records shown to the jury.

The jury saw additional communications that indicated that in the afternoon, Combs’ then-chief of staff, Kristina Khorram, intervened. “Just talk to him,” she asked Ventura in a message. “Sorry don’t want to be in the middle just don’t want him to go back over there.”

Prosecutors also presented a separate exchange in which Khorram instructed an assistant to “say they had a fun drunk night try to get more info.”

The jury has heard and seen Khorram’s name repeatedly during trial. Though she hasn't testified and is not charged with a crime, federal prosecutors have portrayed her as a central figure in the alleged racketeering conspiracy with which Combs is charged and that he has denied.

Khorram has been named as a defendant in civil lawsuits against Combs. She denied the allegations contained in the lawsuits in a March 2025 statement which her lawyer has told ABC News still stands.

"For months, horrific accusations have been made about me in various lawsuits regarding my former boss. These false allegations of my involvement are causing irreparable and incalculable damage to my reputation and the emotional well-being of myself and my family. I have never condoned or aided and abetted the sexual assault of anyone. Nor have I ever drugged anyone," Khorram stated.

"The idea that I could be accused of playing a role in – or even being a bystander to – the rape of anyone is beyond upsetting, disturbing, and unthinkable. That is not who I am and my heart goes out to all victims of sexual assault," Khorram's statement continued. "I am confident that the allegations against me will be proven to be untrue."

When Sean Combs stayed at the InterContinental Hotel in New York City's Times Square in October 2012, he left behind more than $46,000 worth of damages, according to a record shown to the jury at his federal racketeering and sex trafficking trial.

The room was booked under the name Frank Black, an alias Combs often used when checking into hotels, according to the prosecution and previous testimony. The hotel invoice billed Combs $46,786 for damage to the penthouse.

The bill was paid with an American Express card that posted a total $944,059 in monthly charges, according to the credit card statement presented in court. The credit card was paid off by multiple bank accounts at Signature Bank that were controlled by Combs’ company, Bad Boy Entertainment, the jury was shown.

The jury is seeing this collection of invoices, credit card statements and travel records as federal prosecutors work to prove their contention that Combs’ business amounted to a criminal enterprise that existed to fulfill his sexual desires. Combs has denied the charges.

DeLeassa Penland, a special agent who works for the U.S. Attorney’s Office for the Southern District of New York, is using these documents as part of her testimony as a summary witness about the logistics of so-called "freak-off" sexual encounters.

A travel record presented in court showed an American Airlines ticket for a July 29, 2010, flight from Los Angeles to New York that was booked in the name Jules Theodore, one of the escorts with whom former Combs girlfriend Cassie Ventura previously testified she was made to have sex as part of an alleged "freak-off." The return flight on Aug. 1 was booked on United Airlines.

In between those flights, there was a $740.35 charge for Diptyque candles that the jury was shown, allegedly for use during the "freak-off."

Everything was paid for using an American Express card. Penland testified that the Aug. 23, 2010, statement of $108,656.00 was paid off by a Signature Bank account held by Bad Boy Entertainment Worldwide.