I can't advise you on using Boost - there's other forums and mailing lists for that.
The usual thing to do in production environments is to use a reverse proxy to handle SSL for you. That way, you do not need to worry about the implementation details of SSL and just use regular TCP/HTTP/whatever.
Common choices are nginx, Apache, etc ... though they are largely oriented around Linux.
Caddy has releases for Windows which actually handles acquiring (and renewing), using the certificates for you .. you just tell it to proxy to your application.