You can use Resource Monitor in Server 2008+ to view individual connections in real time. In Server 2008 R2 (might be the same in Server 2008) there are two tables in the Network tab that are of interest to you: the Network Activity table and the TCP Connections table.
The Network Active table will give you the local application, the PID, the remote address, and the send and received bytes per second. The TCP Connections will tell you the local address, local port, remote address, remote port, packet loss, latency, and local application/service.
You can consult your IIS logs and see exactly what URLs are being hit (not really real time, but pretty close). You can also utilize Log Parser to see how much data is sent and received if you configured IIS to log that information. IIS.NET provides a lot of information on different ways to use Log Parser to troubleshoot IIS. An example of a query to show you total bandwidth by a user (IP/User Agent) is:
SELECT TOP 30
c-ip as Client,
SUBSTR(cs(User-Agent), 0, 70) as Agent,
Sum(sc-bytes) AS TotalBytes,
Count(*) as Hits
group by c-ip, cs(User-Agent)
ORDER BY TotalBytes desc
This query was found. along with more examples, here