I need a little more clarity, are you talking about one subscription running multiple reports or multiple subscriptions?
This isn't really an answer, but I am 4 points too short to comment yet.
This article has some information. Basically it depends how your RS server is set up. Mine is set pretty low. I never see more than one subscription/report running at a time.
http://msdn.microsoft.com/en-us/library/ms157273.aspx
For my data driven subscriptions I can see the reports run one at a time during testing.
---update--
MaxActiveReqForOneUser value from rsreportserver.config defines number of report running inparallel . default value is 20
P.S. Subscribed reports run in parallel and maximum report running in parallel are 20 by default.