Oracle Web Cache can serve two different sites, with two different SSL certificates.
However, there are two requirements:
1) Each Certificate must be in its own Wallet
2) Eache Wallet must be assigned to a unique IP:port listen combination
This means that you may have two sites on one machine, but each must use a
distinct listen port to differentiate the two. The better alternative is to use
two different IP addresses on that one machine where Oracle Web Cache is
running, configuring each Wallet to a unique IP:443 combination.
So I have 2 virtualhosts with 2 differents Ip adresses and ssl certificates.
The problem is the communication between Web Cache and origin servers. Because it's possible to set only one Origin Server Wallet on webcache manager.
You do not need to encrypt SSL to the HTTP server when you terminate it on Web Cache. Unless your site requires this of course, but this is only important in those environments where you do not trust the network between Web Cache and the HTTP Server.