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Missing condoms, bathroom blunders, and gifts of GOLD-PLATED Playboy jewelry from Hugh Hefner - Holly Madison tells of her worst moments with men. After living at the Playboy Mansion and being Hugh Hefner's number one girlfriend for seven years, Holly Madison exited in in. Madison moved into the Playboy Mansion in August and officially became one of the Playboy founder's love interests. He famously referred to her as his "No. 1 girlfriend" for many years. The former couple, whose untraditional relationship was documented on E!'s The Girls Next Door, called it quits in. Family, friends and fans are mourning the loss of Hugh Hefner, the Playboy founder who died peacefully at his home at the age of 91 on Wednesday. While many of his famous Playmates have expressed their condolences via social media and in statements to ET -- like Kendra Wilkinson, Bridget Marquardt. Madison did not leave the Playboy Mansion on good terms. She wrote about her and Hefner's relationship and breakup and her time at the house in her tell-all book Down the Rabbit Hole. She depicted him as manipulative, controlling and "a spoiled child in an old man's body." Holly Madison, Hugh. Holly Madison is not afraid to speak out about her years as a Playboy bunny. “It was a constant struggle,” Madison told PEOPLE of her seven years living at the Playboy Mansion with former boyfriend Hugh Hefner. “I was trying to sell this image of 'Oh everything is so great here,' but I was miserable inside.”. From her high-school cheerleading days to her time at the Playboy mansion. Hugh Hefner's former “number one” girlfriend Holly Madison has admitted she was “freaked out and ashamed” after taking part in group sex sessions at the Playboy Mansion, and was so traumatised by her time at the celeb-packed pad that she developed a stammer. The year-old was Hef 's main. Holly Madison (born December 23, ) is a model, showgirl, television personality, and New York Times best-selling author. Madison is most widely recognized for her role in the E! hit reality television show, The Girls Next Door and for her own series, Holly's World. In July , Madison released her first book and Years active: –present. As a former Playboy model and main girlfriend to the late Hugh Hefner, nobody knows the dark secrets of the Playboy Mansion better than Holly Madison.