Is it possible to combine VPN and TOR on the same connection?

I'm looking into using a Raspberry Pi 2 between my Router and my Modem acting as an VPN and possibly a TOR gateway (two-in-one). It should just be out-of-the-way and passively/transparently route all traffic simultanously through my VPN provider and do TOR obfuscating. Is it possible at all to use both at the same time on the same connections? Or am I missing something? :)