iptables - here I have basic iptables experiences but I'm lost in PREROUING, POSTROUTING, DNAT, SNAT etc.
Your current rule will only redirect traffic going to <some_server>:555 to 127.0.0.1:555. HTTP uses port 80 and HTTPS uses 443, so neither of those will match the above rule.
Also, instead of DNAT, you'll want to use REDIRECT in this specific case, as you're changing the destination of packets from (not-this-host) to (this-host).
... and your next problem could be that the modern web browsers won't accept just any random certificate when they are supposed to be connecting to Google over HTTPS.
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