Caitlyn Jenner Explains Why She Decided to Start a Family With Kris Jenner Rather Than Transition 20 Years Ago

Caitlyn Jenner has previously revealed that she had planned to transition before her 40th birthday, but when the time came, she simply couldn’t do it. In a video recorded for the Makers Conference, at which Jenner is a featured speaker, she opens up more about why.

“Those were real dark days for me. 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 shares. "I tried to start doing things to make me feel better about myself. I started on hormones; I was a good 36B. I loved them, I thought, This is fabulous,” she says of her first attempt to transition in the ‘80s. “My mission at that point was to transition before I was 40. Got to 39, I just couldn’t go any farther. And like three or four months later, I met Kris [Jenner]. We hit it off from day one and I was very honest with her, I had to be, I was a 36B.”

In her 2012 memoir, Kris Jenner … And All Things Kardashian, Kris details her whirlwind romance with the Olympic athlete. The two were married a month after her divorce from Robert Kardashian was finalized.

Caitlyn explains that at the time she decided to move forward and have a family with Kris, and to leave the hormone therapy behind.

The Jenner family in 2003

“Everything was really heading in the right direction and I made this decision to move on with my life, Kris and I together and this family,” Caitlyn shares. “And, OK, 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.”

Jenner says that she and Kris had an agreement moving forward.

“The rules with Kris and I [were]: Don’t dress up, certainly around the house. If you need to do that, when you’re on the road, take stuff and do that,” Caitlyn explains. “So I did that for years.”

Last summer, after Caitlyn first went public, Kim Kardashian talked about catching her stepfather wearing women’s clothes in her early 20s.

“I was shaking,” Kim said of walking in on the then-Bruce Jenner wearing women’s clothes in the family’s garage. “I didn’t know if I’d just found out his deepest, darkest secret, and he was going to come after me.” When they spoke about it later, Kardashian says Jenner told her, “One day, I’ll talk to you about this. Until then, don’t tell a soul.”