Is there such a thing as "bulletproof" parental control software? With one installation, I want it to work regardless of what I do in terms of adding operating systems or virtual machines to my desktop computer. For instance, have Windows 7, add Ubuntu Linux to have a dual boot system. Again, in Windows 7, add Virtual Box or VMWAre. In either of those two, add Ubuntu Linux again as a virtual machine, etc. In any case, parental controls should still block offensive web sites. This seems to indicate a DNS, router type solution, but I don't want THAT being circumvented by proxies, VPN, alternative IP addresses for virtual machines, or other network type things that I have not thought of yet in this post. I would also like my parental controls mechanism to have a user name and password.
The short answer is that most probably not. As the saying goes "A lock does no more than keeping an honest man, honest." Almost anything can somehow be bypassed if the blocked person is geeky enough.
Of course, you can try the best, but only a good software (probably need a special router) that uses total whitelist (that way VPNs etc will not work) in the router would really seem to do what you want.
Without knowing your use case, we have to make a lot of assumptions here but I can provide a few options that will possibly address your needs. It sounds (based on the use cases you've laid out) that the user you're looking to control is very tech savvy. For this reason, they will invariably be able to overcome any technical solution you put in place, which leads me to prefer the last solution on the list over the other two..
As Yisroel-Tech mentioned, you can configure a router to restrict a given node on your network (eg: a computer) to only allow access to explicitly-listed sites (a whitelist). For instructions on how to do this you would need to look up the documentation for your particular router. Unless it's one that came free with your internet service and is managed by your ISP, the router you have can probably do this.
If you want the monitoring benefits on parental control software, then you can use KVM via software like Mesh Commander (running on another machine; see third video) to take periodic screenshots of what's happening on the controlled computer. The method uses Intel AMT KVM, which connects to the client machine at the BOIS level so works no matter what OS is being run (or even if no OS has been booted).
The best parental control is to put the computer in a public place in the house, like the kitchen. Seriously. Anyone who is using dual-boot systems and VMs is going to be able to outsmart software blocks. In fact their mind will probably be drawn to the challenge.