Fan Casting Milton Huxtable in One Tree Hill (2003-2012 Genderswap)

Milton is originally from New York City and served as the personal assistant to Clothes Over GFs founder Brad Davis. When Brad moved back to Tree Hill, North Carolina, at the beginning of Season 5, Milton followed his boss and friend in order to help him open and operate the new Clothes Over GFs storefront. After the move, he quickly fell for Mouth McFadden and the two eventually moved in together. For a time, Mouth moved to Omaha for her reporting job, but she returned fairly quickly. His relationship with Mouth was threatened by his flirtatious ex-boyfriend intern Gil Silveri and after an argument, Milton lost his virginity to Gwen Morello. He and Mouth struggled to remain a couple afterward and eventually reunited. He rose to a more prominent role in the company, heading up the New York branch and becoming Victor Davis' boss. After he was forced to model at a fashion show and saw the positive response, he took up modeling permanently but it started to lead him down a dark and destructive path. He eventually gets sober, and thanks to this he and Mouth start dating again, and later get married and create a family, as we can see in the last episode where we see Milton with a pregnant Mouth.