Caitlyn opened up about her journey during the shoot and revealed her decision was based on not wanting to live a life of regret.
"If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, 'You just blew your entire life.'"
That's pretty inspiring, if you think about it.
The reality TV star went on to share:
"The last few days of doing this shoot was about my life, and who I am as a person. It's not about the fanfare. It's not about people cheering in the stadium. It's not about going down the street and everybody giving you ‘Atta boy, Bruce,' pat on the back. Okay? This is about your life."
"Bruce always had to tell a lie. He was always living that lie. Every day, he always had a secret, from morning till night."
We're so glad Caitlyn was able to make her reveal on her own terms.
Ch-ch-check out the behind-the-scenes footage from her photoshoot with Annie and Vanity Fair (below)!
Not only do the two celebs jam out to some of The Material Girl's greatest hits, but the Queen of Pop talks a bit about her personal life -- like the time she made out with Michael Jackson! Oh, don't worry, there's plenty of dancing and twerking too.
Ch-ch-check out Madonna and James as they get their karaoke on, carpool style (below)! Be sure to let us know if you're shocked by the singer's MJ story!