You should not be clearing the session anywhere except for logouts. The 
multiple characters problem would be easy to solve if you sent the 
character ID in each request and used a corresponding key to store in the 
session. For instance your URL to play could be mygame.com/play/character_id
  
You could also just try and send the character id with every request and 
reading and writing from the database every request, it may be fast enough, 
databases are really smart about caching nowadays so you may be prematurely 
optimizing something that doesn't need it.

-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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