Sean ‘Diddy’ Combs Hamptons Freak Off Details Aired at Trial Sean ‘Diddy’ Combs Hamptons Freak Off Details Aired at Trial Skip to content Communities North Fork Jamesport Mattituck Orient Riverhead Shelter Island Southold The Hamptons Montauk Quogue Sag Harbor Sagaponack Southampton Water Mill Westhampton Beach NYC Palm Beach Home Pros Digital Editions Dan’s Best of the Best Subscribe Things to DoEvents CalendarView and Post Events Books & Authors Concerts Comedy Fairs & Festivals Film Fitness & Outdoors Galleries & Museums Kids & Families LGBTQ+ Nonprofits & Philanthropy Pets & Animals Seasonal & Holiday Shopping Theater Dan’s EventsVisit Dan’s TasteArts & Culture Artist Profiles Books & Authors Galleries & Museums Performing Arts Music, Film & TV Food & Drink Recipes Restaurants Bars, Breweries & Distilleries Wine & Wineries Celebrity NewsLocal News Crime & Police Politics Health Business Education Environment Obituaries Real EstateLifestyle Fashion & Style Hotels & Inns Kids & Family Nonprofits & Philanthropy Party & Event Photos Wellness Dan Rattiner’s Stories Search for: Open Search → Dan’s Taste Summer Series Presented by Wilmington Trust Police & Fire Sean ‘Diddy’ Combs Hamptons 'Freak Off' Details Aired at Trial By Ashna Balroop 4 minute 07/01/2025 Share Sean “Diddy” Combs stands as he is arraigned on a superseding indictment ahead of his May trial on sex trafficking charges, in New York, U.S., March 14, 2025, in this courtroom sketch. REUTERS/Jane Rosenberg//File Photo Hamptons references galore emerged in testimony at Sean ‘Diddy’ Combs sex trafficking trial at Manhattan federal court, where he is accused of forcing women to have drug-fueled orgies he called “freak offs.” Among those who took the stand were Cassandra Ventura, Combs’ ex-girlfriend and singer, who alleged that she was forced to participate in these freak offs, including in the Hamptons with Combs and an escort named Dave. She testified that she blacked out during the freak off due to being intoxicated with the nervous system depressant drug gamma-hydroxybutyrate, or GHB, and woke up naked in the shower — then continued. “I felt pretty horrible about myself. I felt disgusting. I felt humiliated,” Ventura testified. “I didn’t have the words to show how horrible I felt. I couldn’t talk to anyone about it.” Close Get the Full StoryNews, events, culture and more — delivered to you. Thank you for subscribing! Email This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply. Sign Up This incident isn’t the only connection Combs has to Long Island. He was the owner of 40 Hedges Banks Drive, a just under one-acre property in East Hampton for approximately two decades. He would regularly use the house to host ultra-exclusive parties, often with Hollywood’s elite in attendance. Plaintiffs from other lawsuits against Combs contend that these gatherings weren’t what the public perceived them to be, alleging that their abuse happened at these elite parties. In a lawsuit filed on Oct. 14, 2024, a man claimed he was 16 when he attended one of the rapper’s parties in the Hamptons in 1998. After meeting Combs, they moved to a more private area where he was ordered by Combs to remove his pants so he could examine him, according to the lawsuit. Combs allegedly told the boy it was “a rite of passage” and “the route to becoming a star.” The lawsuit additionally claims Combs told the boy it was a way for him to prove himself, asking the teen: “Don’t you want to break into the business?” In another October 2024 lawsuit, a man who worked for a security firm at one of Combs’ white parties alleges that he sexually assaulted him. While at the event, he became ill after consuming two alcoholic drinks provided to him by Combs. The man alleges Combs pushed him into a van and pinned him down, assaulting him. Another woman, who was a 17-year-old at the time, claims to have drunk a drugged alcoholic drink at Combs’ 2004 Fourth of July Party in the Hamptons, causing her to lose consciousness. She woke up to “throbbing pains in her vaginal and anal areas,” and was only able to leave the party after “agreeing not to contact the police in exchange for the return of her purse and phone,” according to the lawsuit. Additionally, Leslie Cockrell, a music scout, alleges in a February 2025 legal complaint that she was drugged and assaulted by Combs at a Hamptons party in 1999. The security guard who drove Cockrell home after the assault told her to be grateful Combs had chosen her and to accept what had happened, according to the complaint. The jury was deliberating with no verdict reached in the seven-week-long trial as of press time If you or someone you know has experienced sexual assault, the Rape, Abuse, Incest & National Network’s sexual assault hotline offers confidential, free support to survivors and their loved ones at 800-656-HOPE (4673). Vetted Hamptons Resources Hamptons Classified Access our trusted network of local professionals and browse employment opportunities in the Hamptons. 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