End-to-end user anonymity is provided in electronic commerce or other types of online transactions through the use of an intermediary. An intermediary machine, which may be implemented in the form of a set of servers or other type of computer system, receives communications from a consumer or other user, and generates and maintains an alias for that user. Connections between the user machine and any online vendor or other web site are implemented through the intermediary using the alias. When the user desires to make a purchase from a given online vendor, the intermediary may present the user with a number of options. For example, the user may be permitted to select a particular payment card number and real destination address as previously provided to the intermediary. The intermediary then communicates with the online vendor and supplies intermediary payment information, e.g., a payment card number associated with the intermediary rather than the user, along with appropriate authorizing information and an alias destination address, e.g., a third party physical shipping address for deliverable goods, an alias electronic address for downloadable material, etc. The online vendor charges the purchase to the intermediary, and redirects the delivery of the goods or services to the destination address provided by the intermediary. The intermediary charges the payment card number of the user, and arranges for the redirection of the delivery to the real user address. In this manner, the invention provides complete end-to-end anonymity for the user, even when the user desires to enter transactions involving purchase and receipt of deliverable goods and services.