This chapter consists of selected excerpts from a female to male (FTM) transgender recreational athlete (Riley) and his advisor (Maylon) during the time period that Riley completed his master's thesis in a sport management program. As part of his qualitative study on the lived experiences of recreational transgender athletes, Riley wrote about his own experiences of transitioning and training for running. Griffin and Caroll point out how the gender binary leaves little space for transgender and gender fluid athletes to participate in sport. In order to reflect their Collaborative Autoethnography (CAE) process, the chapter deals with different narratives so that neither voice is lost for the sake of consensus. It then presents the co-telling of the stories that highlight three significant experiences: silencing past sport experiences, ongoing efforts to give enough 'gender cues', and post-surgery and running.