In this work, we investigate the profit maximization problem for a wireless network carrier and the payment minimization for end-users. Motivated by recent findings on proactive resource allocation, we focus on the scenario whereby end-users who are equipped with device-to-device (D2D) communication can harness predictable demand in proactive data contents caching and the possibility of trading their proactive downloads to minimize their expected payments. The carrier, on the other hand, utilizes a dynamic pricing scheme to differentiate between off-peak and peak time prices and applies commissions on each trading process to further maximize its profit. A novel marketplace that is based on risk sharing between end-users is proposed where the tension between carrier and end-users is formulated as a Stackelberg game. The existence and uniqueness of the non-cooperative sub-game Nash equilibrium is shown. Furthermore, we explore the equilibrium points for the case when the D2D is available and when it is not available, and study the impact of the uncertainty of users' future demands on the system's performance. In particular, we compare the new equilibria with the baseline scenario of flat pricing.Despite end-users connectivity with each other, the uncertainty of their future demands, and the freshness of the pre-cached contents, we characterize a new equilibria region which yields to a win-win situation with respect to the baseline equilibrium. We show that end-users' activity patterns can be harnessed to maximize the carrier's profit while minimizing the end-users expected payments.