As Rahul stated, it is a common Chrome and an OSX bug. I was having similar issues in the past. In fact I finally got tired of making the 2 [yes I know it is not many] additional clicks when testing a local site for work.
As for a possible workaround to this issue [using Windows], I would using one of the many self signing certificate utilities available.
Recommended Steps:
- Create a Self Signed Cert
- Import Certificate into Windows Certificate Manager
- Import Certificate in Chrome Certificate Manager
NOTE: Step 3 will resolve the issue experienced once Google addresses the bug...considering the time in has been stale there is no ETA in the foreseeable future.**
As much as I prefer to use Chrome for development, I have found myself in Firefox Developer Edition lately. which does not have this issue.
Hope this helps :)