Research on gay and bisexual men’s sexual position self-label (i.e., being a top, bottom, or versatile during anal sex) has revealed only independent snapshots of its development by focusing primarily on the influence of penis size. Moreover, the basic chronology of development of the sexual position self-label has barely been addressed. In response, we implemented a survey of 282 gay and bisexual men that measured demographics (including height and penis size), age of sexual recognitions, sexual position self-label, and attitudinal constructs suggested by previous literature as important (e.g., pleasure, control, anxieties, and gender typicality). Results suggested that men’s sexual position self-label was learned over a 15-year timespan. Ages of first same-sex genital manipulation and first anal sex experiences were related to age at first self-labeling. With respect to predictors of labels, a multivariate path model was created. The model did not support the direct importance of penis size, but identified indirect paths that linked penis size to top/bottom identification (e.g., smaller penis sizes leading to topping-anxieties and thus, a bottom label). Finding bottoming to be pleasurable and the importance of sexual control dynamics were the only two direct predictors. The path model substantiated the reliance both bottoms and tops show towards seeking (or not seeking among tops) gender typical, sexually dominant partners. It also supported previous evidence regarding race; specifically, while race may activate differences in sexual behavioral dynamics, it is not a great predictor of the sexual position self-label. This study shows that sexual position self-labeling has enormous complexity and cannot be reduced down to penis size.