Reddit mentions of Counter Hack Reloaded: A Step-by-Step Guide to Computer Attacks and Effective Defenses (2nd Edition)

School, here is a textbook I used.

I'm not an expert, but here are some of the resources that I've learned a lot from

http://vulnhub.com - My favorite so far has been Hackademic_RTB1 using g0tm1lk's walkthrough.

BackTrack is now Kali so you'll want to check that out. And in case aren't already using it, you'll probably want to use something like VirtualBox to set up your labs. The #kali and #vulnhub channels on irc.freenode.net are really helpful.

Some other books I've enjoyed are CounterHack by Ed Skoudis and everything by Richard Bejtlich.

Let me know if you have any questions. I probably won't know offhand, but wouldn't mind helping you find out.

Ok - Here's a list of books I've read in the last few years

• Gray Hat Hacking - The Ethical Hacker's Handbook - Really good intro to Software Sec / Reverse Enginering / Disclosure
  
• Counter Hack Reloaded - A 'bible' of phased attacks - classic book.
  
• Guide to Network Defense and Countermeasures - Technically designed as a 'prep' book for the SCNP, it's still a great read about IPS, IDS, NetSec Policies, Proxies, firewalls, packet filtering, etc
  
• Hacking Wireless Exposed - Great intro read on 802.11 sec.
  
• CWNA/CWSP Exam Guide - Assumes 0 knowledge about RF. More intense than Hacking Wireless Exposed, but also easier to learn from. I went into this book knowing very little about RF, left it feeling confident. Well written.
  
• Snort 2.1 - Self explanatory, but a book about the IDS system Snort. Not perfect, but again, great starter book.
  
• The Web Application Hacker's Handbook - The best for last. The holy grail of web hacking. Second edition SHOULD be coming very soon, depending on the drop date may be worth it to wait.
  
  As you can tell, I'm big on the technical books, and even exam prep books. This is just a selection, but I think it's a good starter pack to some different fields.
  

stormehh has some good points.

I agree, and would argue that you are better off learning the fundamentals at this stage in your life. I understand your urge to get out there and explore different tools and techniques as fast as possible (trust me, I've been there myself), but take my word for it when I say that you will get more out of it when you understand the underlying concepts/technologies/protocols.

This might sound old fashioned, but read these books. It's a lot of material, but well worth the effort. You can get all three of them used for about $75:

"Computer Security: Art and Science" - Matt Bishop

"The TCP/IP Guide: A Comprehensive, Illustrated Internet Protocols Reference" - Charles M. Kozierok

"Counter Hack Reloaded: A Step-by-Step Guide to Computer Attacks and Effective Defenses (2nd Edition)" - Edward Skoudis & Tom Liston

Good luck to you, and follow the light side of the force.