I am not clear about what you're saying. I know that VoiceOver announces the name of each selected item as it's added to the collection of things selected, but so do most screen readers. But I have never seen VoiceOver have the ability, after you've created that collection of selected items, read the names in that collection "all at once" after selection is complete.
The way I'm reading the initial request, and it would be under Windows, is that if Janet is selecting Janet.doc, Brandly.pdf, Group.txt, and Spreadsheet.xlsx, that afterward there should be a way to trigger what amounts to a "read all for selected items only," where the screen reader would say something like, "Selected, 4 files, Janet.doc, Brandly.pdf, Group.txt, Spreadsheet.xlsx."
I have never worked with a screen reader that does this. It will announce each as it's added to the selection collection, but there's no post-selection way to have the screen reader give you a file-by-file list of what's been collected.
Brian - Windows 10 Pro, 64-Bit, Version 2004, Build 19041
A gentleman is one who never hurts anyone's feelings unintentionally.
~ Oscar Wilde