This paper describes a novel approach to support multiple resellings of DRM-Protected contents. The approach allows a consumer to resell his/her content (license) to a second consumer who can also resell the same content to a third one, and so on. This reselling process can continue till the license is resold N-times. To ensure that the reselling process is secure and fair, the approach has built-in security measures to enable a buyer to verify that the license for sale is not faked/forged and that it is resalable before engaging in the payment process. In addition, the approach ensures fairness in a reselling process, i.e. the buyer will not get the license without making the due payment, and the reseller will not get the payment if he does not surrender the license. These properties are achieved through the use of a number of building blocks, including a License Revocation List (LRL), a digital token called Reselling Permission (RP) and a special contract signing protocol called Reselling Deal Signing (RDS) protocol. A security analysis of the method demonstrates that the approach is effective in thwart possible threats and attacks on license reselling.