Born in 1960, Nayland grew up on the Upper West Side of New York City in a home that embraced the counterculture of the 60s. But even though there were books of historical erotica around the house, sex was still a topic that was not to be discussed. As an adolescent, Nayland began to feel attraction towards men and they began to explore the porn theaters and erotic bookstores in Times Square where they had their first gay sexual experience.

After they attended Bard college in upstate New York, Nayland decided to come out after they moved to Los Angeles in the early 80s. Some early explorations in kink were less than ideal which led eventually led Nayland to instruct other kink enthusiasts about how to navigate consent when it comes to kink play.

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