More complex =/= more secure. Tor, Whonix, Tails, et all have sections in their wikis covering potential tunneling setups and their thoughts on efficacy and rationale behind them.

From the Tor wiki:

> You -> X --> Tor --> X

> No research whether this is technically possible. Remember that this is likely a very poor plan because [#You-Tor-X you -> Tor -> X] is already a really poor plan.