AceShowbiz -

Nearly three years before Bruce Jenner debuted her new identity as Caitlyn Jenner, her former stepson Rob Kardashian asked Olivia Culpo about transgender women competing in the Miss USA Pageant. He asked the contestant whether or not they could win the title.

As seen in a video, Rob was a guest judge during the 2012 competition. During the Q&A portion in the final round, Rob was selected to read one of the questions. "Would you feel it would be fair that a transgender woman wins the Miss USA title over a natural-born woman?" he asked Olivia.

After thinking for a few moments, Cuplo responded to it, "I do think that that would be fair, but I can understand that people would be a little apprehensive to take that road, because there is a tradition of natural-born women."

"But today, where there's so many surgeries and so many people who have a need to change for a happier life, I do accept that, because I believe it's a free country," she added, drawing big applause from audience. She was named Miss USA shortly after.

The clip surfaced online just days after Caitlyn's Vanity Fair cover debut on Monday, June 1. While Rob hasn't spoken yet about Caitly's gender transition, his sister Kim Kardashian revealed that Rob didn't recognize Caitlyn when he first saw the cover.

"Who is this woman and why do I care?" Rob asked Kim after she sent him the cover photo. When Kim explained it was their father, Rob "was like, 'Oh my God, she's beautiful!' Then he called her and they had a love fest."