Holly Madison Shares 'Traumatic' First Experience With Hugh Hefner

Holly Madison is opening up about her time as a Playboy bunny and her relationship with Hugh Hefner. During a recent appearance on the Power: Hugh Hefner podcast, Madison talked about one of her first encounters with the mogul.

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Holly Madison’s “Traumatic” First Date With Hugh Hefner

Madison said she was “nervous” after scoring an invite to spend a night out with Hefner and hopeful that she might get invited to live at the famed Playboy Mansion. One of Hefner’s girlfriends had just moved out and Madison wondered if she might get to take her room.

“I didn’t really know what went on with them sexually,” she said, referring to Hefner and his many girlfriends. “I knew there must be something and I was prepared for that. I wasn’t prepared for what would eventually happen.”

Madison said that, after hanging out in a nightclub, she accompanied Hefner back to the mansion, along with a group of other women. “I wasn’t necessarily expecting to have sex that night, I thought it would be more of a first date – even though obviously it’s not a very traditional first date,” she said.

Madison continued, “I thought it would be more the type of thing where I saw what happened, saw what was going on. If I wasn’t comfortable with it I wouldn’t have to do anything and I could make my decision on whether I wanted to come back for date No. 2 or not.”

The Night Was A ‘Traumatic Experience’

However, she and Hefner did end up having sex–and Madison was not pleased with the way it went down, calling it a “traumatic experience.” She shared, “He was literally pushed on top of me and after it happened, I was just mortified and embarrassed and it had way more of an emotional impact on me than I thought it would.”

“I thought he was really smart, I really looked up to him, so I liked him and it wasn’t that the idea of possibly having sex with him repelled me so much – I know that’s not relatable to a lot of people because they’re like ‘Oh he’s an old man, gross,’” the Girls Next Door star said.

“It was more the group aspect that was really out of my comfort zone and just the feeling of ‘Wow, okay, that happened. Everybody knows it happened,'” she added. “I kind of all of a sudden felt like everybody was going to know about me, and I was horrified by it.”

Madison, who went on to date Hefner from 2001 to 2008, asked him if she could move into the mansion the next day. “I felt like by moving myself in and getting what I wanted from the situation, that was demanding respect in a way. I felt like if I didn’t do that I was just going to be haunted by this experience,” Madison said.