Restricting access to new content

Hello,

I was wondering if anybody knows of a way to restrict access to posts after a specific amount of time after a user registers (not free), and will only show him the new content if the user pays an annual upgrade fee. For example:

John pays $20 for a new membership on Jan. 21st, 2013 and gains access to the entire site. Content is added to the site regularly and after a year, John must either pay a $5 fee to see content added after Jan. 21st, 2014 or he will be restricted to seeing only the content added before Jan. 21st, 2014 until he pays the fee.

The above would repeat each year.

Is this at all possible?

Thank you for your help.

Best,
Eric