I have the same problem: our users need to connect with WSAM from a Windows 2008 R2 Terminal Server to a 3rd party site (SA-6000). 1st user is able to open the tunnel, but 2nd one receive an error when try start WASM. I've did some tests from from the same Win2008 against our Juniper SA-2500 and been able to connect multiple concurrent users. The 2rd party company did the same tests on their site, connecting to their VPN, and been able to have multiple concurrent connections on the same TS too. The issue happens only when connect from our site to 3rd party site. I could not find any explanation for this behavior.
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