Justin Bieber, Then 19, Poses Shirtless at 2014 Diddy Vodka Party

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Justin Bieber was photographed partying shirtless with Sean “Diddy” Combs at a 2014 event for the the rapper’s vodka. Bieber was 19 at the time.

As captured in dozens of images from inside Diddy’s Ciroc celebration, the “Lonely” singer, now 30, went bare-chested at the event, which was held at Atlanta nightclub Vanquish Lounge in February 2014. Bieber — clad in opaque, dark sunglasses, a backwards hat and chain necklaces — was in the middle of the action at the club, rubbing elbows with hip-hop icons including Rick Ross and Jermaine Dupri. Several photos feature Diddy, now 54, putting his arm around the two-time Grammy winner and grinning for the camera.

While Bieber was not photographed consuming any alcohol — he was spotted holding a bottle of alkaline water brand Aquahydrate, which Diddy had invested in — the “Baby” artist was underage at Diddy’s vodka promotional event, as the drinking age in the United States is 21. He reportedly attended the party with his then-girlfriend, Chantel Jeffries, who was 21 at the time.

Later that night, Bieber shared his own photo with Diddy and friends via instagram. No longer shirtless, the “Ghost” singer posed with Diddy, Ross, Dupri, and more in a group shot. Bieber bent his head down and held his hands together in prayer.

The pictures have resurfaced in the wake of the federal charges against Diddy, who was arrested last month and charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution. (The disgraced rapper is currently sitting in a Brooklyn jail while he awaits trial and has pleaded not guilty to the charges against him.) In the 14-page indictment against him, many references were made to Diddy’s now-infamous parties, during which alleged sex crimes occurred.

Old footage of Bieber and Diddy continues to resurface in the wake of the “I’ll Be Missing You” artist’s downfall — including a 2009 video in which a 15-year-old Bieber spends 48 hours with Diddy, then 40.

“Where we hanging out and what we’re doing we can’t really disclose,” Diddy told the camera. “But it’s definitely a 15-year-old’s dream.” He also quipped that he had “custody” of Bieber for the weekend.

Two years later, in a joint interview with Jimmy Kimmel in 2011, Diddy noted that Bieber “knows better than to be talking about the things that he does with Big Brother Puff on national television.”

Though Bieber has yet to publicly speak out about the allegations against Diddy, a source told Us Weekly in an article published on Thursday, October 10, that the singer “is in a hard place mentally right now” as he grapples with the case against his former mentor.

“He has such a history with Diddy and the allegations against him have been hard to process,” the insider continued, noting that Bieber — who wants “nothing to do” with the disgraced star — “has been advised to stay as far away as possible from anything and everything related to Diddy.”