Can I redirect all traffic through TOR?

I need to anonymously redirect multiple sources of traffic (browser, other apps and possibly old online games).
Is this secure using software like proxifier or should I use a VM and configure it to use the proxy for everything?

Does this even work with TOR?

It's nothing illegal, but if they notice my real IP, I'd probably lose my accounts that are quite valuable to me.

You can do that through setting up a transparent proxy all filter traffic through tor, you might want to check out this
https://trac.torproject.org/projects/tor/wiki/doc/TransparentProxy

as above excellent advice

Yes, and if you redirect it through "low profile" router, they won't even notice! I use it mysefl!