Differences of Sexual Development (DSDs) are amongst the most common birth defects in humans. Alarmingly, the incidence of DSDs has increased significantly in the last few decades, and this rise is attributed to our increased exposure to endocrine disrupting chemicals (EDCs). Furthermore, some EDCs are predicted to have far reaching effects beyond the exposed individual, causing disease that persists over multiple generations. Our study aimed to determine the transgenerational effects of estrogenic EDCs on penis and testis development, and fertility in males. Gestating F0 female mice were exposed to 100ug/kg of diethylstilbestrol (DES), a clinically relevant EDC. The effects of DES were monitored in the F1-F4 male descendants. Reductions in pregnancy rate and mating index were observed up until the F4 generation in DES descendants. The anogenital distance (AGD) was also significantly reduced in DES descendants, confirming a decrease in androgen production. Hypospadias rates were significantly increased up to the F3 generation, and testis weights were significantly reduced up to the F4 generation. Sperm motility was also significantly impacted up to the F4. These results indicate a transgenerational effect of DES on multiple reproductive parameters including fertility, AGD and testis development. This study suggests that exposure of pregnant mothers to DES has significant implications for multiple generations of DES descendants and raises concerns about the effects of exposures to multiple estrogenic EDCs present in our environment.