USB debugging is performed by a program called "adb", which you install on a computer. You then enable USB debugging on the phone (usually via the hidden "developer options" menu, which you unhide by tapping repeatedly on the "build number" in the software information in the system settings - but it's a long time since I ran Android 4.4 so can't guarantee it was already done there). Then if you connect the phone to a computer via a USB cable and USB debugging is enabled on the phone you can use ADB (Android Debug Bridge) to execute a range of commands on the phone.
The way you do it is by typing adb commands on the command line of your computer. So from the directory you have adb installed in (or from anywhere if you've added that directory to Windows' equivalent of the $PATH, the list of directories that the system looks in when you type a command) you would for example type:
adb devices
which should return the serial number of your phone (probably together with some messages about starting an adb daemon). If it does then adb is working, if not you should try to work out why not.
Then you can get it to list the contents of a directory by typing
adb shell ls directory
where the "directory" should be specified using a unix-like format (i.e. "/" rather than "\" between subdirectories). You need to use unix formatting for the directory path because this command is being sent to the android device, and android is based on the linux kernel. The syntax of this command is: "adb" (the program that talks to your phone) "shell" (execute linux shell command on the phone) "ls directory" (the command you want executed). "ls" is the unix command to list the contents of the specified directory - if I remember DOS correctly the equivalent in Windows would be "dir".
So for example to see the top level of the file system (if it will let you) type
adb shell ls /
or the user-accessible part of the internal storage by typing
adb shell ls /sdcard
or equivalently
adb shell ls /storage/emulated/0
So just put in the path to the directory you want to list the contents of.
Then if I wanted to write the output to a file, rather than just list it on the screen, I would type
adb shell ls directory > myfile.txt
where the ">" is unix shell for "output to the file named here". That's the bit I don't know the Windows equivalent for, but I assume that it exists.