If you are just looking for a simple solution, you can customize a a "Send To..." right click shortcut that will invoke your python script with the command line arguments of the files to convert.
To add a Send To shortcut, it depends on if you are using Windows 7 or a 32 bit prior version.There are instructions HERE to add a custom Send To... shortcut. You could send all the files to a single folder and invoke your python script or invoke it with the selected files as command line arguments.
Send To Toys works in 64 bit. With Send To Toys you could have the your python script and all the shell escaped file names placed on the clipboard when you right click, then paste the constructed command into the shell. I use this method a lot because it only takes seconds to construct.
You can also add a right click shortcut by tweeking the registry to invoke a shell command (your python script) with the selected files as targets. You can either manually tweek the registry or use something like RightClick Extender.
A bit more work, you can write a custom ContextMenu Class form and respond to the form in a .NET language. This would include C# or Ironpython.
If you really want a Pro kind of implementation, you could modify the source code of the new open source version of Image Resizer. The c++ source the context menu handler is here. But these last two suggestions seem like way more work than needed...