Due to the abundance of attractive services available on the cloud, people are placing an increasing amount of their data online on different cloud platforms. However, given the recent large-scale attacks on users data, privacy has become an important issue. Ordinary users cannot be expected to manually specify which of their data is sensitive or to take appropriate measures to protect such data. Furthermore, usually most people are not aware of the privacy risk that different shared data items can pose. In this paper, we present a novel conceptual framework in which privacy risk is automatically calculated using the sharing context of data items. To overcome ignorance of privacy risk on the part of most users, we use a crowdsourcing based approach. We use Item Response Theory (IRT) on top of this crowdsourced data to determine privacy risk of items and diverse attitudes of users towards privacy. First, we determine the feasibility of IRT for the cloud scenario by asking workers feedback on Amazon mTurk on various sharing scenarios. We obtain a good fit of the responses with the theory, and thus show that IRT, a well-known psychometric model for educational purposes, can be applied to the cloud scenario. Then, we present a lightweight mechanism such that users can crowdsource their sharing contexts with the server and obtain the risk of sharing particular data item(s) anonymously. Finally, we use the Enron dataset to simulate our conceptual framework, and also provide experimental results using synthetic data. We show that our scheme converges quickly and provides accurate privacy risk scores under varying conditions.