The model recounts suspecting that Caitlyn--then Bruce--was cheating on her mother, Kris Jenner, after she and sister Kylie discovered Caitlyn's makeup, among other things.
At one point, Kylie and I thought he was cheating on my mom because he had makeup and nail polish. One time we found those squishy boob things, We found wigs. And one time I actually ran into her. In this house.
Kendall mentions one encounter with Bruce (as Caitlyn) in their home, after waking up early one morning (Bruce's preferred time to dress as a woman pre-transition.)
As I was coming back out, my dad was coming down the stairs, in, like, a wig and makeup and shoes — the full nine. And she didn't see me. I literally froze. Please don't turn left. Because she could either turn left or turn right. Thank God she turned right and — to this day! — has no idea that happened. That was the first time I had ever seen her.
She also reveals that Caitlyn had informed her ex-wife, Kris, that she enjoyed dressing as a woman as early as their "third date."
Kendall acknowledges that Bruce Jenner's Olympic legacy created an almost mythical perception of hyper-masculinity.
It's super-ironic to think about now, but it's something I can thank my dad for: how much of a tomboy I was. That's why I think the whole thing — her transition — was really hard for me, because I was like 'But you taught me everything tomboy!
Despite the initial grief of losing the father she grew up with, Kendall eloquently affirms her unconditional love and wholehearted support of Caitlyn, in her continued journey as a trans woman.
We're very accepting of people and of being different and being who you are. We're not judgmental. But obviously it's strange having your dad, who was so male, completely reverse. It is definitely a gnarly experience."
I knew it was going to have its rough phase. But it's all supernormal now. It's not weird at all. Sometimes I look at a picture of my dad when she was a guy, and it makes me a little sad — get emotional. You have to get past it — you've got a new person to love. It's kind of a blessing in disguise — if that's not the wrong way to say it.