Shouldnt be a problem, i have achieved this just by using jmail more than once on a page.
To add multiple recipients you have to do something like:
dim oMsg
set oMsg = server.CreateObject("jmail.smtpmail"

oMsg.serveraddress = "smtp.ision.net.uk"
oMsg.subject = "Your order Confirmation"
oMsg.sender = "andrew.butt@dcseworld.com"
oMsg.addrecipient "ian@dcseurope.com"
oMsg.addrecipient "vikki@dcseurope.com"
oMsg.addrecipient "nick@dcseworld.com"
oMsg.addrecipient "nick@retrographics.fsnet.co.uk"
oMsg.Body = sbody
oMsg.execute
set oMsg = nothing
To send a completely different email just repeat the above code, should work fine (obviously substituting the server details etc. for your own).
Hope this helps!
Nick (Web Developer)
nick@retrographics.fsnet.co.uk
nick.price@myenable.com