![Ultimate ladies' man Hugh Hefner had sex with MEN in the 80s as he 'tested the boundaries' of his sexual appetite Ultimate ladies' man Hugh Hefner had sex with MEN in the 80s as he 'tested the boundaries' of his sexual appetite](https://www.thesun.co.uk/wp-content/uploads/2017/09/nintchdbpict000356672387.jpg)
Ultimate ladies' man Hugh Hefner had sex with MEN in the 80s as he 'tested the boundaries' of his sexual appetite
![Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel](https://www.sun-sentinel.com/resizer/rN1k4C9dABSQlBFXnY16iWX2tSk=/415x311/top/arc-anglerfish-arc2-prod-tronc.s3.amazonaws.com/public/IHKZTQF5LJAYZEPYQHW454UDXI.jpg)
Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel
![Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel](https://www.sun-sentinel.com/resizer/2xnDsjaM_nl16Xdq3BGuB9yYbxA=/415x311/top/arc-anglerfish-arc2-prod-tronc.s3.amazonaws.com/public/2A2MZUZRGZGPJCIQZXFTQZKXWI.jpg)
Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel
![James Parkley on Twitter: "that one time hugh hefner put a dick on the cover of playboy https://t.co/ZcflkXGVDM" / Twitter James Parkley on Twitter: "that one time hugh hefner put a dick on the cover of playboy https://t.co/ZcflkXGVDM" / Twitter](https://pbs.twimg.com/media/DYBox7WVoAA0ReH.jpg)
James Parkley on Twitter: "that one time hugh hefner put a dick on the cover of playboy https://t.co/ZcflkXGVDM" / Twitter
![Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel](https://arc-anglerfish-arc2-prod-tronc.s3.amazonaws.com/public/SIGKSNODTNHUPB6ZYPPLB4QBVI.jpg)
Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - South Florida Sun-Sentinel
Playboy founder Hugh Hefner, who shook up American morality with an ideal of swinging singlehood, dies at 91 - Los Angeles Times
![Sam Kalidi on Twitter: "That one time Hugh Hefner put a dick on the cover of Playboy. https://t.co/JeVxbcaqb7" / Twitter Sam Kalidi on Twitter: "That one time Hugh Hefner put a dick on the cover of Playboy. https://t.co/JeVxbcaqb7" / Twitter](https://pbs.twimg.com/media/DKyMIFKU8AApdYv.jpg)