Hugh Hefner's secretary, Mary O'Connor, has died this week aged 86 years old.
O'Connor had worked alongside Hefner for a long time; according to People magazine she had been a fixture at Hefner's mansion for more than four decades.
However, late on Sunday night Hefner broke the news of her death via his social media account. He posted on Twitter: "Mary passed away today. We loved her more than words could say."
Hefner's announcement sparked a wave of tributes and well wishes from others who had known her.
Hefner's new wife Crystal Harris expressed her sadness by writing, "Hef's long time secretary & my dear friend Mary O'Connor has passed away. It's a very sad day here at the Playboy Mansion. We love you Mary."
O'Connor is said to have been at Hefner's side through three marriages, and although she was not a prominent figure out front with Hefner, she is attributed to organizing many things behind the scenes.
In recent years she had come more in the spotlight by making appearances in various reality TV shows, such as "The Girls Next Door."
O'Connor also featured on the show "Kendra" with Kendra Wilkinson-Basket.
Upon hearing of her passing, Wilkinson-Basket wrote: "RIP Mary O'Connor. She was an amazing person who helped me through so much. But I know she's happy with her boo Captain Bob. "
Here's a video clip of one of Marry O'Connor's appearances on Kendra.