Holly Madison and the Mess
Evidently, Hugh and Holly let the dogs defecate and urinate on the carpet in their room every day. Hugh would wake up every morning and clean up piles of mess while Holly slept. Needless to say, this relationship didn't last until the end of Hugh's life.
The Hugh Zone
His quarters weren't specifically geared for naughty encounters. He offered his space to anyone looking to get away. As long as they were quiet when he needed them to be, Hef let his guests relax with him while he sipped chicken soup and did administrative work for his publication.