If you use your tor bridge to connect from your local network to tor, then use tor to connect to your VPN (You would be going from intranet to VPN server's tor bridge, from tor to VPN server), only your entry node to tor would know your external IP from your intranet. But, this would allow your VPN server to know your intranets external IP (which is what you have said you are trying to advoid). You could find an open socks or http proxy that runs on port 80 or 8080, then use that to connect to your tor bridge. These are easy to find on the internet (from lists) or scanning yourself. intranet > socks/http proxy > tor bridge > vpn > destination. They also have pay for services with more "Secure" http/socks proxies. You can always get a shell account on a shell server and use netcat to relay from there to your tor bridge (instead of using a proxy). Or you could set up another external box on a different network. The easiest solution is using a free or pay for proxy to connect to your tor bridge (i know i am repeating myself there). What ever you use to connect to the tor bridge could use this proxy, or you could use tsocks or proxychain to encapsulate that (to force it to use your proxy). LOL or use a http/sock proxy (not on your own external network) to connect to a free VPN (which would be easier to set up than all of this), and then connect to tor. intranet>open/free proxy>free vpn>tor>destination. This option would completely remove your external network from the equation. And provide three external hops to your destination (between your intranet and destination). I hope this helps! Ask if any of this is confusing, but i'm sure it addresses most/all of your concerns. (last repeat, you need an open/free socks/http proxy to hide your intranets IP from your external networks server).