It sounds like good clean fun to me.
"A clip began doing the rounds earlier this week that showed the Barstool Sports boss naked, sitting astride a blonde woman who was equally naked — except for the black leather dog collar she had around her neck and the metal leash that Portnoy was holding."


Haven't seen the video but it looks like he has good taste in women. I also agree with him about it being ridiculous that the company stock would drop over something like this.
“A stock is down because somebody has consensual sex? Are you f–king kidding me?”
He even urged his followers to buy Penn’s shares while the price was lower.
“I would jump on this dip and I would f–k it,” he said. “No pun intended.”