General Readers
For the reader who is not on a technical undergraduate course I intend to make these pages a good overview of Anonymity on the Internet. I will try very hard to be as non technical as possible or provide links to good articles explaining the technical terms.
If you’re at all like me though you’ll soon want more detail 
For a good general entry point for those of undergraduate or lower technical level try the Tor Overview. Whilst obviously biased towards Tor and it’s goals it will give you a good overview on motivations for anonymity systems (at least from one perspective) and a basic idea how some of them work as well as the issues surrounding Anonymity apps such as information leaking from your web browser, or that you may leak yourself.
If you find this too technical you’re probably better off boning up on terms like “proxy” etc beforehand. Admittedly this is very difficult for non computing professionals who require a basic knowledge of these systems. Unfortunately when dealing with this topic the fact is largely unavoidable that you will need to know a variety of technical terms just so you don’t get completely lost.
For those on a computing degree or above
In general (especially for an academic) the Anonymity Bibliography is the best place to start. Bear in mind however that many of the papers are very technical and whilst many of them provide very readable introductions and summaries a lot of the content will likely go over the head of the average reader.
Once you’ve done your background reading, the technical description of any of the major implementations currently out there is a great next stop, as this will allow you to understand a system that whilst still unfinished is out there and working (for a given value of working) today. You can also dive into the code if that’s the sort of thing that turns you on.
