I've never done it myself, but I think you would want to use something like WinRunner. I also think that the JProbe people offer something along those lines. Their web address is www.klgroup.com
I work in a group that gives a lot of attention to just this. We use LoadRunner. Might be a good exercise to thread an applet to make your 50+ requests on the web server.
Microsoft produce the Web Application Stress tool, formerly known as Homer, for testing on IIS. I've used it on test sites, it seems to do the job and it's free. Their page is at: http://webtool.rte.microsoft.com/
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