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Home » Escort Opens Up About Diddy's 'Freak Offs' — and Why Sex Was in Very Short 'Increments' (Exclusive)
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Escort Opens Up About Diddy's 'Freak Offs' — and Why Sex Was in Very Short 'Increments' (Exclusive)

Jack BogartBy Jack BogartJul 4, 2025 12:11 pm0 ViewsNo Comments
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Escort Opens Up About Diddy's 'Freak Offs' — and Why Sex Was in Very Short 'Increments' (Exclusive)
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NEED TO KNOW

  • A male escort allegedly hired by Sean “Diddy” Combs for “freak offs” with Combs’ ex-girlfriends Cassandra “Cassie” Ventura and a woman using the pseudonym “Jane” is speaking out for the first time
  • Identified by Jane as “Don,” the escort exclusively tells PEOPLE that sex during the “freak offs” was “limited” to “maybe 30-seconds to one-minute increments” because Combs would often “interject”
  • Combs was convicted of two prostitution-related charges, but acquitted of the more serious sex-trafficking and racketeering charges he faced

A male escort allegedly hired by Sean “Diddy” Combs is speaking out for the first time, revealing intimate details about the music mogul’s so-called “freak offs.”

In an exclusive interview with PEOPLE, the escort and model — identified during the trial as “Don” — claimed that the “sexual activity” he participated in during the “freak offs” was typically brief. He said it was often interrupted by Combs, 55, when Combs thought “things were moving too quickly.”

“Whenever sexual activity would occur, it would always be in maybe 30-seconds to one-minute increments,” Don tells PEOPLE.

(The interview took place days before Combs’ conviction on two prostitution-related charges on Wednesday, July 2. Combs was acquitted of the more serious sex trafficking and racketeering charges he faced.)

Don also says that Combs first hired him on Valentine’s Day 2016 for an evening with Combs’ ex-girlfriend, Cassandra “Cassie” Ventura, now 38. He claimed he met the former couple “two or three times in total.”

Combs’ attorneys did not immediately respond to PEOPLE’s request for comment on Wednesday.

Combs allegedly hired him several more times beginning in 2021, that time for encounters with one of the rapper’s subsequent girlfriends, a woman who testified under the pseudonym “Jane” during Combs’ sex trafficking trial.

According to Don, Diddy hired him for the last time in 2024.

Referring to his experiences with Jane, which she referred to as “hotel nights,” Don tells PEOPLE, “In the moment we would kiss, [Combs would] be like, ‘Okay, alright. You go stand back over there, and you go over there. Okay, so did you like that kiss? What did you like about it? Tell him what you liked about it. Tell her what you liked about it.’”

Government exhibits (file 2A-614)

Don says he “never” had “any type of real prolonged sexual activity” with Jane during the “hotel nights.”

“They would have sex and I would be off to the side,” Don says.

Speaking on the brevity of his “sexual activity” with Jane, Don tells PEOPLE, “I couldn’t imagine it being satisfying too much for any of us [escorts] because it wasn’t a long period of time.” 

Sean "Diddy" Combs sits with members of his defense team for a conference ahead of his trial next month on sex trafficking charges, in New York, U.S., April 18, 2025, in this courtroom sketch

Both Jane and Ventura have accused Combs of coercing them to have sex with multiple male escorts throughout the course of their respective relationships with him, which was the basis of the sex trafficking charges against Combs. The jury ultimately found Combs not guilty on those charges. Jane testified that Don was the first escort she had sex with during her three-year relationship with Combs. 

Don recalls: “It was always, ‘Okay, kiss her neck, kiss her breast. Okay, now go over there. Okay, you ready for sex? You ready for sex?’ And then, ‘Okay, wait. Stop, stop, stop. Okay, now you go over there. You go over there. What did you like about that? Okay, now we’re going to smoke. We’re going to order some food.'”

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Cassie and Shawn Dearing
Sean ‘Diddy’ Combs Acquitted of Most Serious Counts, Convicted on Prostitution Charges
Sean "Diddy" Combs gestures as he speaks with his defense team before the day's session of his sex trafficking trial in New York City, New York, U.S., June 18, 2025 in this courtroom sketch

Combs would “interject” if he felt that Jane “would kind of rush into something sexual” when she was “maybe wanting to kiss too quickly or to touch too quickly or to engage in a sexual act too quickly,” Don claims.

Want to keep up with the latest crime coverage? Sign up for PEOPLE’s free True Crime newsletter for breaking crime news, ongoing trial coverage and details of intriguing unsolved cases.         

“He would say, ‘Wait, wait, wait. No, you guys relax” and “kind of break it up,” Don says.

Don also recalls Combs saying, “Okay, let’s dial it back. You’re too much. We don’t got no place to be. Don, you got some place to be? No, you got no place to be? Okay. Let’s let this thing flow.”

Don

Combs behaved similarly during his encounters with Ventura, Don says.

Cassie and Shawn Dearing

Former Escort Booked by Diddy Reveals How the ‘Tone’ Allegedly Changed During His Last ‘Freak Offs’ with Cassie (Exclusive)

Sean "Diddy" Combs attends Sean "Diddy" Combs Fulfills $1 Million Pledge To Howard University on October 20, 2023 in Washington, DC.

While on a Break with Diddy, Ex Watched Escort Have Sex with a Woman: Here’s Why Diddy ‘Exploded’

“Sometimes we would joke too much, and he would be like, ‘Hey, y’all are losing the moment,’” Don claims Combs told him and Ventura.

As with Jane, Combs and Ventura would allegedly “engage in sexual acts in front” of Don, while “any sexual contact” Don had with Ventura “was limited to 30 seconds to maybe one minute,” Don says.

“He would always be like, ‘Okay, wait. Okay, break, break, break,’” Don claims.

“In the whole night of being there eight or nine hours, altogether, sexual contact, there’s probably 10 to 12 minutes worth of actual sex,” he continues. “And this was broken up so many points throughout the night — and that’s [including] touching, that’s [including] everything.”

If you or someone you know has been sexually assaulted, please contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673) or go to rainn.org.

Read the full article here

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