Is it possible to hand-negotiate an SSL/TLS session?
No, this is not possible, even if you copy &amp; paste data to/from another program. The reason is that SSL is a binary protocol, and telnet won't pass through arbitrary binary data. Moreover, upon connection, it does some protocol negotiation, and this is probably the reason for connection reset.

There are programs, like openssl s_client, which set up SSL connection for you and let you type the data by hand. For example, you can use it to connect to a HTTPS server and type the request manually, as you do with HTTP and telnet.