Vanity Fair Writer Reveals His Common Ground with Caitlyn Jenner

When it came down to choosing who would best tell Caitlyn Jenner's next chapter in the story to accompany Vanity Fair's spectacular cover photo by Annie Leibovitz, the magazine's editor reportedly chose someone with whom he thought the former Olympian could bond.

That person was Buzz Bissinger, 60, a contributing editor at the magazine, as well as the author of the book Friday Night Lights, and co-author with LeBron James of Shooting Stars. He is also someone who has written and spoken about his fetish for leather, his sexual exploits with other men, and about his love and adoration for cross-dressing.

"I know [it's] obviously very different from gender dysphoria," Bissinger told CNN.

Nevertheless, that was something that gave Bissinger some "common ground" with Jenner, he said.

"I have been a cross-dresser with a big-time fetish for women's leather," said Bissinger, "and an open critic of the often arbitrary delineation between men's and women's clothing."

He said Jenner was heartened to learn Bissinger had himself faced criticism for revealing his true self to the public. In fact, Bissinger told Sirius XM that his writing about cross-dressing was "ridiculed, mercilessly."

"We all carry secrets, and I got to the point I was tired of carrying around this secret," Bissinger told Sirius XM's Xorje Olivares. "It's empowering to me. What's the difference? It makes me happy. ... I know what it's like to be different, and how a lot of people will ridicule you, as I was ridiculed."

"In American society it is very, very hard to be different," he added. "It is scary to be publicly different because the reaction by many people is horrendous. So, as I said, we shared that common bond. She is scared about the reaction and continues to be scared."

Bissinger told Sirius XM he recognizes Jenner does not represent "the typical transgender man or woman, absolutely not... dealing every day with discrimination, with injustice, and with hate."

"Anytime you sort of cross gender, or anytime you wish there was no gender, anytime you walk into a department store and there's a men's section and a women's section, why can't people buy whatever the hell they want?" Bissinger asked Olivares rhetorically. "Instead, [you get] the stigma of having to go into the women's section, and some of the sales people look at you, [saying] 'what are you doing, sir, what do you want this for?' It enabled me to know that difference is very hard. That isn't to suggest that what I do is anywhere near as powerful and intimidating as what Caitlyn Jenner did, but it creates empathy. And it creates a need for tolerance [that] too many Americans simply do not have."

That was painfully obvious, he said, when he read the online comments posted to articles about his interview with Jenner. "[A total of] 126 comments... every single one of them was negative, and cynical, and tasteless, and disgusting, and suspicious," he lamented, saying we as a society have a long way to go. "There is such an element out there that engorges and thrives on hatred."

Bissinger told out CNN anchor Anderson Cooper that he spent "hundreds of hours with [Jenner] the man over a period of three months. Then I spent countless hours with the woman," starting soon after ABC's Diane Sawyer sat down with Jenner in February. Bissinger said he spent four to five days at a time with his subject, adding, "I even helped him move."

With Bissinger, Jenner identified as Caitlyn.

"The use of pronouns are very important in the gender community, and I have to admit I screwed them up, and Caitlyn screws them up, too," Bissinger said.

"My miscues have nothing to do with intolerance," he clarified in Vanity Fair, pointing to his own history with gender-nonconforming attire. "But because it is a strange story regardless of all the important inroads that have been made by transgender men and women into the cultural mainstream."

Bissinger said ultimately, the similarities between writer and subject made him more sensitive to Jenner's transition, which he called "the most remarkable story I have ever worked on in 38 years as a journalist."

He acknowledges that the story (and the subject) were special, calling himself "the only writer in the world with unlimited access to Jenner for a story of global interest, witness to the final months of one of the most iconic male athletes before he disappears and a woman appears in his place."

Bissinger said the positive reaction to the Vanity Fair cover and Jenner's transformation was a pleasant surprise, and that Jenner herself "feels a greater social responsibility, to advance the cause, not just transgender men and women, but to advance the cause of tolerance and the embrace of difference. I think she was shocked at how phenomenal the response has been. Vanity Fair got 14 million hits" for its online video.

An internal memo from Vanity Fair's parent company, Conde Nast, indicates the magazine's web site "generated its highest-ever single-day traffic with more than 9 million unique visitors."

Listen to Bissinger describe his bond with Jenner over sports and cross-dressing, below, and about her new reality series.