One night, Caitlyn Jenner writes in her memoir The Secrets Of My Life, there was a party going on on the ground floor of a Westin hotel, which she wanted to attend as her true self. But she couldn’t, for fear of being recognized as Bruce Jenner, so she went to bed instead, feeling trapped inside both herself, and the hotel. It was torture.
Unable to take Caitlyn out in public where she could talk to people, she still wanted to “find a little window for the woman inside of me to surface," so she would find pockets of time to release her inner woman.
While on the road (both before Kris Jenner and after Bruce married her) there were times when Caitlyn could roam free after a few hours of shoddily makeup and wig application, leg shaving, and putting on an ill-fitting dress and heels.
Here are the times then-Bruce went out dressed fully as Caitlyn in order to feel free:
She would book hotel rooms on the ground floor, because “this was a great place in which I could dress as I desired and walk around a long as I made sure to get a room on the ground floor. Which of course I did.”
“As Bruce, I always liked going to Vegas not for the gambling or the garishness but because it was the best place of all to dress up, the only locale where you could do whatever you wanted and no one would notice…As always, I had my routine down to perfection. I left the house in Hidden Hills. Almost immediately I drove to the back of a nearby parking lot. I applied makeup in the car, then tried on several wigs I kept hidden underneath the backseat and picked out the one that not only suited my mood but best concealed my identity,” Caitlyn writes.
“Next came putting on a favored outfit while still inside the car. Then five hours of blissful driving through hot and lonely desert, until I got to a Holiday Inn parking lot on the Vegas outskirts and wiped all the makeup off and removed the wig and wiggled out of the clothes.”
Bruce would then check into the hotel room and repeat the dress up routine all over again. “There can’t possibly be a place in the world that has more mirrors per hotel room than Vegas. Which is why I brought more than one outfit, since it was so much fun to try them on."
Bruce would leave Vegas and drive home dress up once again.
Once back in Malibu, or Calabasas, Bruce would do the following in order to be free and dress as a woman in public (without having to talk to anyone for fear of being outed as Bruce.)
Drive around in a Porsche to feel the breeze, calling Bruce a “facade.”
Would walk around outside LAX.
Would often go to the movies, dressed up and alone, to sit in the dark as a woman.
Walk hotel lobbies, saying “maybe I am getting careless, maybe I am getting bold.”
After marrying Kris, dress up for 20 minutes at a time when no one was home.
Wear full face makeup to bed while on the road, with a do not disturb sign on the door.
Steal Kris’ gowns to wear.
Steal makeup from the Kardashian girls.
Steal heels from TV sets when Bruce did appearances.
“Bruce wants to have never existed in the first place,” Caitlyn writes of her decision to finally transition.
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