In 1991, Tula Became the First Transgender Woman to Pose Naked in Playboy

Caroline was the first openly transgender woman to appear in Playboy in , nearly a decade after News of the World exposed her. She was featured in the September issue of Playboy , in a pictorial, "The Transformation of Tula", as an acknowledged transgender person. Cossey now began an active social life as a woman, concealing her past living as a boy. When she told him, rather than rejecting her, he merely asked if she would convert to Judaism. At sixteen she moved to London and worked at a variety of low-wage jobs.