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Map Pesqueira, 19, an incoming sophomore at the University of Texas at Austin, said Jenner has always been an inspiration for him.
"I remember...the Vanity Fair cover," he told "Good Morning America." "When I was in high school and that was just...that was just so eye-opening for me to see somebody who has an influence be able to come out and be themselves."
"Especially as a trans person," he added. "It was just so inspiring to me."
Pesqueira said he was awarded a three-year ROTC scholarship that was set to begin his sophomore year, and has always been passionate about going into military service.
"I grew up in Military City, U.S.A., San Antonio, Texas," he said. "I was constantly on posts and on bases...getting to know what the military was all about, and I instantly fell in love with it."
But in April, Pesqueira's college aspirations were cut short after the Pentagon began implementing its new transgender military policy. He says he was told he would be disqualified from the program, and lose his scholarship.
Former Olympic athlete and reality TV star Jenner said she was "devastated" by the ban.
"I really wanted to come...and meet Map and find out about his story," she told "GMA." "This whole military ban has been...I'm devastated by. I can't believe it's happening."
Pesqueira began transitioning in 2018, after he was awarded the scholarship. But under the new policy, anyone who is taking hormones or has already undergone a gender transition will not be allowed to enlist.
After losing his scholarship, Pesqueira started a GoFundMe to raise money for his higher education, and has already raised over $27,000 in donations from people across the country.
"To be truthfully honest, I did not expect it to get more than maybe $100 in donations, a couple shares on Facebook from my family," Pesqueira admitted. "But when the media started coming to me inquiring about my story, it just took off."
ABC News previously reported on Pesqueira's story in April.
Eventually, his story even caught the eye of the Caitlyn Jenner Foundation, which provides grants to organizations that help empower and improve the lives of transgender people.
"I want to see what I could do to go out and reach out to people -- to get involved with my foundation," Jenner said. "Because there's a lot of trans people out there that need a voice and need help."
Pesqueira said he is glad he came out with his story, saying, "I was very fearful to 'cause I didn't think I would get much support, people wouldn't care. But I was very wrong."
Jenner surprised Pesqueira with a $25,000 check from the Caitlyn Jenner Foundation to go towards his higher education.
"I know once it's all over with, that you'll come back and help," Jenner told Pesqueira. "Get that education."