Extremely Smart Calendar app needed!
Plenty of Calendar apps, such as Fantastical, can parse your needs with natural language, but I am not aware of any that can string together all your events as you have stated. 

However, you can certainly do this with Automator/AppleScript and iCal. There are many resources on the web that will give you instructions and snippets that you can string together with Automator without any programming knowledge. Many of those scripts can be found here on AskDifferent.