Holly Madison Reveals Weird Group Sex Nights at Playboy Mansion

Holly Madison has provided detailed accounts of the group sex encounters she participated in with Playboy founder Hugh Hefner during her time as a resident of the Playboy Mansion.

During a May 5, 2026, appearance on the Let’s Be Honest podcast hosted by Kristin Cavallari, Madison described these events as compulsive sex nights and characterized the atmosphere as a really weird scene.

Madison, who previously shared claims about her time at the mansion on the In Your Dreams podcast, explained that these group sessions typically occurred twice a week, often following outings.

According to Madison, the sessions involved her, Bridget Marquardt, and Kendra Wilkinson taking turns with Hefner.

She noted that while some women were active with Hefner, others would act as though they were active with the other women present, though she clarified that this was not really the case.

Madison described the physical environment of the room as being silhouetted by giant screens of porn that were playing during the encounters.

She recalled that the experience was marked by the women talking shit with each other and stated that nobody liked it.

Madison characterized the overall experience as a nightmare, stating that everyone involved attempted to get it done as fast as possible.

This dynamic stood in contrast to the time Madison spent with Hefner individually. She described the one-on-one nights as being very suburban and more tame in nature.

The practice of these group sex nights eventually ceased as the lifestyle of the mansion residents shifted. Madison attributed the end of these events to the success of the Playboy reality series, which premiered in 2005.

The rise of the television series led to a decrease in the frequency with which the group went clubbing, which had typically preceded the sexual encounters.

Madison stated that there was no formal discussion regarding the end of the practice, but that she, Wilkinson, and Marquardt were all in agreement that they no longer wished to participate.

She explained that because they stopped going out, the initiation of these nights simply stopped occurring.