I'm sure there are folks on here that have worked either directly in, or on contract for, the military.  But if you don't find anything else out, my wife's got a good friend in military IT / security, and I might be able to link you up for a chat.  PM me, if nobody else gets you some info, and I'll see if I can make a connection.

If I had known that I was going to be interested in InfoSec back in high school, I think I would have signed up with the Navy/Airforce.  They have some nice toys.  Unfortunately I wanted to save trees and animals so I was into Biology, oh well hindsight...  You will probably find it more rewarding to sign up with the military if you want to get those skills up and put them to good use, specially now-a-days.  Good luck man!

The Marines perform IT Security tasks as well.  Just wanted to throw that out there.  But, I would agree with ziggy_567 as far as the Air Force is concerned.  I know that the Marines use Core Impact as do the other branches, but don't know what else they do since I have been out of the loop since 2002.

Thought I would throw my sorry 2 cents in on this topic as someone that has been pen testing for longer than I care to admit.  Having a degree is good but not absolutely critical. However, it will definitely open doors faster for you, that is if you don’t having any contacts or rep. Having a good reputation because you know your stuff and a few friends can catapult you into the industry faster that you can say “buffer overflow” regardless of diplomas or certs.   But hey, you might just learn something if you go to college, hopefully more than the 3 French words I remember years later,lol!   You might want to get a 4 year degree in computer science, but your masters in business. This will give you a lot of flexibility and still make you a prime candidate for a security firm.  Flexibility is a key to survival in life and a great mental attribute to have for hacking. What if you find you hate doing pen testing for a living?  For most of us it requires a lot of travel and I have seen a number of marriages end due to this. Traveling 30 or more times a year seems cool when you’re young but believe me it gets old fast. Good god every hotel room is the same!  What really sucks is you don’t have any time to sight see! I have been to every major city and I could not really tell you much about them.  

Working with the military can be a good career and it can mean being hired by the DOD if you are a civilian, just make sure you can get a security clearance.  In other words, if you go to college drink responsibly!  If you ever get any kind of arrest you will find it very hard to get a security clearance. Well, unless you run for president or congress, lol!   Anyway, I have one acquaintance that has a dream job working for the DOD but has to live in Germany pen testing military bases throughout Europe.