Whatever was happening, he had the ruse going since high school. https://ghostarchive.org/archive/JloLy

While the exact age Fleming was transitioned is unknown, early photos posted to his aunt’s Facebook show he was raised as a boy, and only began presenting in feminine clothing in 2016 when he would have been approximately 14 years old. His family members have been careful not to publicly identify him as transgender, but his grandmother referred to him as her “grandson” in an early photo.