I just got IRC to work with TLS, 256Bit encryption, on my 486 with Windows 95b. Here are the instruction (should work for specific applications, except web browsing)

I attached a zip file containing all the required stuff.

1 - copy the SSLWrap folder in program files
2 - copy the dlls in windows\system (you can also put them in the sslwrap folder if you don't want to install them system-wide)
These are MSVC++7 DLL and OpenSSL 1.0.2 dlls (not the SSE version because I got it to work on my 486)
3 - install the two .exe files (one is Microsoft Active Accessibility 1.3, it will recommend to install IE4, but ignore that, it work if you have ie3). The second one is Winsock 2 update (both are required for the OpenSSL dlls)
4 - run wrap from where you installed it.

Here an example for IRC

5 - Go in service and add the service you want to use with encryption, for example you can add IRC, set type to "SSL Tunnel", put listen host to "localhost" and listen port to "whatever you want, say 6123", set Remote host to the irc server url "example, irc.libera.chat" then set Remote port to the TLS port of that irc server, for example, 6697
6 - Open IRC, add a server, put "localhost" for the host and 6123 for the port. Can also be localhost:6123 if you put it all in one field.

Then you can connect to that server. You should see the SSL log in Wrap.

Wrap must stay open for the whole time you use that connection.

Note : That procedure should also work on Nt4 / Win98, in that case ignore the Winsock2 update)