You  may want to 'stack' a LoginModule in front of JBoss Portal's login module 
(see its login-config.xml).  In your LoginModule implementation, you can 
implement the business rules, etc. for your requirements.  It sounds like from 
your reqs. that you will need your own table for storing at least the last 5 
passwords as well, possibly keyed to a JBoss Portal user.

As for LoginModules and stacking, you need to understand JAAS Security, and how 
to configure LoginModules for JBoss Application Server, and then you need to 
study the Portal's schema a bit to see how you want to 'integrate' with it.  
It's relatively easy to find articles about JAAS on the web, you can get the 
JBoss AS guide to learn about writing LoginModules for JBoss, and you can 
download the docs and source for the portal as well.

Good Luck!

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