A system and method is provided for handling network communications between a client and a target server on the Internet to protect the privacy and anonymity of the client. For a session between the client and the target server, a routing control server sets up a routing chain using a plurality of Web servers randomly selected from a pool of participating Web servers as routers for routing messages between the client and the target server. To prevent traffic analysis, an "onion encryption" scheme is applied to the messages as they are forwarded along the routing chain. A payment service cooperating with the routing control server allows a user to pay for the privacy protection service without revealing her real identity.