Your problem is that the openssl import libraries (or static libraries, if it's a static openssl build ... though "/bin" usually indicates a dynamic build) are not being found.
What's the name of these import libraries ? (I'm used to seeing "libssl.dll.a" and "libcrypto.dll.a" but it depends upon which compiler built them.)

If it helps, there are ppm packages for both Net::SSLeay and IO::Socket::SSL at the sisyphusion repo (and probably elsewhere, too):

ppm install http://www.sisyphusion.tk/ppm/Net-SSLeay.ppd
ppm install http://www.sisyphusion.tk/ppm/IO-Socket-SSL.ppd
[download]

Net-SMTP-SSL-1.01 (which is pure perl) builds trivially against those ppm packages for all versions of perl later than 5.6.2 ... or I could upload ppm packages for it, too, if need be.
I don't know whether Net-SMTP-SSL actually *works* on Windows - the test suite passes, but it's about 7 years old and doesn't actually test the functionality of the module.

Cheers,
Rob