1.  Ancient Greek and Roman societies
It’s still debated by historians whether or not male condoms were used this far back in time. Ancient societies in Greece and Rome mainly viewed birth control as the woman’s responsibility (there’s a surprise) and the only documented forms of birth control from this time are female-controlled, like pessaries (similar to a diaphragm). Most historians interpret texts from this time as referring to “coitus interruptus,” otherwise known as “withdrawal,” or, “was that the doorbell?”.

2. 15th century
Limited use of glans condoms (condoms that only cover the head of the penis) is documented in Asia prior to the 15th century. As was common for birth control at the time, glans condoms seem to only have been used by the upper classes. In China, the may have been made of oiled silk paper, or lamb intestine, but in Japan, they were often made of tortoise shell or animal horn. Ouch.