The 66-year-old reality star and Olympic gold medalist opened up in a revealing video interview at this year's AOL Makers Conference in Rancho Palos Verdes, California on Tuesday.
"Those were real dark days for me," Caitlyn said of her life in 1986. While still living as Bruce Jenner and having gone through two divorces -- first from Chrystie Scott in 1981, after nine years of marriage, and then from Linda Thompson, after four years -- the celebrated athlete felt like life was at a "crossroads."
"I [had] a house in Malibu, I basically stayed there for six years," Caitlyn recalled, "and I really started struggling with my identity, [asking], 'Who am I?'"
"I tried to start doing things to make me feel better about myself," she shared. "I started on hormones. But yeah, I was a good 36B, and I'm going, 'Oh, God. OK.' I loved them, you know, I thought: 'This is fabulous.'"
"My mission at that point was to transition before I was 40," Caitlyn explained. "I got to 39, and I just couldn't go any farther."
"Three or four months later, I met Kris [Jenner]. We hit it off from day one," said Caitlyn, who started dating Kris in late 1990. The couple tied the knot five months later in April 1991. "I was very honest with her [from the beginning]. I had to be, I was a 36B. But [I told her], 'I'm a good person. I'm fun.' We had a great time."
Caitlyn came into the marriage with four children, son Burt and daughter Casey from her first marriage and sons Brandon and Brody from her second marriage. Kris came in the union with four kids of her own -- Kourtney, Kim, Khloe and Rob, from her marriage to late attorney Robert Kardashian. Together, the couple had two more kids, Kendall and Kylie.
"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," said Caitlyn. "[I decided], 'Okay, I gotta get rid of these gender things, and get off hormones and this and that.' And I actually had my boobs removed. I never told anybody that."
But the couple still had rules about the athlete's behavior, in regards to her desire to transition.
"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,'" she revealed, adding that she "did that for years."
In 2014, Kris filed for divorce and the media speculation drove Caitlyn to consider suicide.
"I thought, 'You know what's the easiest thing to do? I got a gun in the other room. Just go in there and end it. Stop the pain. Stop the hurt. I won't have to deal with nobody,'" Caitlyn said. "But I thought, 'I don't want to end my story that way.'"
Caitlyn went on to publicly share her story of transition, sitting down with for a highly publicized interview with Diane Sawyer in April 2005, and making her debut on the cover of Vanity Fair in June.
For more on Caitlyn's attempts at transitioning in the '80s, check out the video below.