In a video shown Tuesday at the Makers Conference in Rancho Palos Verdes, California, where Caitlyn (formerly known as Bruce) hosted a Q&A, the I Am Cait star opened up about that time in her life.
"Those were real dark days for me," Caitlyn said of the late 1980s, after she had been through two divorces (one from Chrystie Scott in 1981 and the second from Linda Thompson in 1986).
"I got a house in Malibu, I basically stayed there for six years, and I really started struggling with my identity, about 'Who am I?' " Caitlyn recalled. "I tried to start doing things to make me feel better about myself, started doing hormones. But yeah, I was a good 36B. I loved them, you know, I thought: 'This is fabulous.' "
"My mission at that point was to transition before I was 40. Got to 39 – I just couldn't go any farther," Caitlyn said. "And three or four months later, I met Kris [Jenner]. We hit it off from day one. I was very honest with her – I had to be, I was a 36B."
By 1991, Kris and Caitlyn were married. They went on to have two kids together: Kendall, now 20, and Kylie, now 18: "It was a great time in my life. My greatest accomplishment is my kids," Caitlyn said.
"Everything [was] really heading the right direction, and I made this decision to kind of move on with my life and Kris and I together and this family," Caitlyn continued. "And [I thought], 'Okay, I've got to get rid of these gender things and get off hormones and this and that.' I actually had my boobs removed. I never told anybody that."
As for his relationship with Kris, now 60, Caitlyn said the two had set some ground rules.
"The rules, kind of, with Kris and I [were]: 'Don't dress up, certainly around the house, if you really need to do that, when you're on the road take stuff and do that,' " Caitlyn said. "So I did that for years."
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In addition to her attempts to transition, Caitlyn also opened up about her childhood.
"God's looking down, and he's making little Bruce, and he's thinking: 'Okay, what are we going to do here? Let's make him a good-looking guy, let's make him smart, let's give him great drive, let's make him athletic – in fact, this will be fun, let's make a really athletic kid out of this one,' " Caitlyn said. "Then God sits back in the chair and he goes: 'Wait a second, nobody has that many great qualities,' and he chuckles a little bit and he goes: 'Ah. Let's give him the soul of a female and let's see how he does!' "
According to Caitlyn, who went on to become a widely lauded Olympian, sports became the "place where I could hide and be the quote, 'man,' everybody expects you to be."
"I remember the next morning [after winning gold at the 1976 Montreal Olympics decathlon] I got up, went into the bathroom, put the gold medal on, not a stitch of clothes on, looked in the mirror and thought: 'What the hell am I going to do with my life?' " Caitlyn recalled. "It kind of just planted the seed for the rest of my career. I could hide, just being what everybody expected, the 'Bruce Jenner.' "
In October 2013, Kris and Caitlyn separated, and by December 2014, the divorce was finalized.
Caitlyn spoke openly about her transition for the first time during her April 20/20 interview with Diane Saywer and made her public debut on the cover of Vanity Fair in June.
"I thought: 'What's the worst thing that can happen?' " Caitlyn said in the Makers Conference video of her decision. "I transitioned. Okay, is that the end of the world? No, I'm still here."
"America's Golden Boy actually wound up being America's Golden Girl," she added. "So, maybe in God's eyes, this is why he put me on this earth."