Question

When was the wedgie invented and how

Answer 1

Explanation: It came from Ancient Rome

Mr. Shioptard's answer is a good one, but the first recorded instance of the wedgie comes from Ancient Rome. As Caesar was crossing the Rubicon, on his way to invade Italy, he didn't want to get his new toga wet, so he ask a nearby slave to hold up the hem as he crossed the river.

Answer 2

No one is for sure how it started but it is believed someone might have been in a uncomfortable position for their buttock