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Kylie Jenner does Caitlyn Jenner's makeup for the 1st time ever: I want you 'to be free'

The 71-year-old retired Olympic gold medal-winning decathlete said she never thought this day would come.
/ Source: TODAY

Caitlyn Jenner had a luncheon in town, and needed someone to do her makeup. Lucky for her, she knows somebody.

In a first, Jenner had her makeup done by daughter and beauty mogul Kylie Jenner whose cosmetic company has made her a multi-millionaire. The younger Jenner had never done her dad’s makeup before, and said doing it was “the highlight of my life,” but jokingly warned her dad, “I’m really expensive.”

Caitlyn and Kylie Jenner. YouTube

The 71-year-old Olympic gold medal-winning decathlete featured the makeup session on her YouTube channel, and the glam session was filmed in the Kylie Cosmetics offices, a trendy space with a large fluorescent “KYLIE” on the wall. “My little baby that I used to change her diapers, this is her office,” Jenner said to the camera, beaming.

As the pair settled in and the 23-year-old makeup mogul worked, she took the opportunity to ask her dad some questions, including if Jenner ever thought this day would come.

She didn’t. “No, I never thought, I mean, I was 65 years old before I finally came through this,” she said, referring to coming out as transgender in 2015. “I had to raise everybody else, and I had such a life,” she said, but knew it was “my time to be me.”

Kylie made an astute observation, that despite she being the makeup maven in the family, her dad has a lot more experience wielding a lip liner or eyelash curler. "You've been doing your makeup longer than anybody that I could imagine," she said to her.

Caitlyn's first big media appearance after coming out was the cover story for Vanity Fair in 2015. Jenner said it was the first time she ever had her makeup done professionally, even though she’d been doing it on her own, in secret, for thirty years. “I thought I died and went to heaven,” she told her daughter of the Vanity Fair experience, which included spending a day trying on a truckload of clothes.

Speaking of a question that has been raised in years since, the younger Jenner asked her dad how she felt about still being called “dad,” which, she said, sometimes confuses people.

“I feel it was one of the best decisions I made,” Caitlyn said. “I’m the dad, I’ve been the dad the whole way, I will be their father until the day they die, or I die.”

She added that from the beginning she felt that “I gotta do it my way…. everybody out there has to do it their way.”

As Kylie used a makeup brush on her dad’s face, smoothing out foundation, Caitlyn spoke of the time before she came out, saying, “You know how complicated and how difficult it was to live my life, sneaking around, lying to people, doing this, doing that, everything just to kind of survive. I don’t have that anymore.” Caitlyn highlighted how supportive her family has been.

The end result!YouTube

“I want you to be able to be free and be yourself,” Kylie said. “There’s just no other way anyone should live.”

After applying a nude lip with some gloss, Kylie’s work was revealed to her dad, who hugged her daughter, said she loved her (and her makeup!) and then looked at the camera, saying with a smile, “Not bad for 71!”