At least to the age of Romans.
Although it wasn't sexual with the Romans, it was cultural.
When a warrior was wounded in battle to the point where he could no longer fight, he was sent back home to his family. The whole family would dress him up in baby clothes. (Which pretty much meant that he was wearing a dress, made changing easier) Including diapers, which he used, and was treated like a baby until he was able to take care of himself. I don't really know why the Romans went through such extravagent ways to go through the healing process, perhaps the warrior was changing social class because of his wounds and needed to start over. Or maybe the Romans really like diapers as a culture.
But thats the oldest I've seen it. But it would also depend on your definition of infantillism. ANR (Adult nursing realtionship, an adult female breastfeeding an adult male or female) has been around for as long as people have liked breasts and what comes out of them.
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