How to perform the following shenanigan with PI3?

Question

linux

Again my strange question.
Is it possible to implement the following scheme programmatically.
Computer - PI3 - USB stick.
1. A flash drive is inserted.
2. PI3 performs a fraud deleting a file.
3. After work, PI3 skips the flash drive in Windows.
Connection method - usb wire connecting PC and pi3, power, flash drive into pi3