Situation: Classic ASP application, using a custom Application Pool. Default settings.
On some IIS7 machines, IIS decides to serve only one page at a time.
Have you changed "Managed pipelined mode" on Application Pool to "Classic" (default is "Integrated")? If not, try with classic.
I don't know if it would help in any way. I have long ago ceased to fight to get classic ASP apps to work with IIS7. (Not that I can say, the apps are truly nice and correct, but they worked in earlier versions.)
And try turning buffering off for test pages and make them spit something out in each iteration. Buffering (and caching) might've changed in IIS7. Maybe they are processed concurrently after all and simply buffers are too big to see the difference.
That's all that comes to my mind right now.
I assume you are testing with very simple case. Your app doesn't (neither test pages nor global.asa) use any strange objects that are common to both requests and so need locking.
If it isn't an issue with the debug settings, I've found that you can experience similar behavior when using session variables in ASP in IIS 8.
I don't know that this is IIS 8 specific, but "ASP guarantees that only one request from a Session will be executing at any time." http://msdn.microsoft.com/en-us/library/ms972335.aspx