A distributed anonymous payment interleaved wagering system is disclosed, including an interactive processing device constructed to receive a request for processing a payment; communicate interactive processing device data and a request for an anonymous payment identifier; receive the anonymous payment identifier; lock the interactive processing device for a period of time; communicate anonymous payment identifier; receive gaming session data; unlock the interactive processing device; the process controller or wager controller constructed to: create an anonymous payment identifier; associate the anonymous payment identifier with the interactive processing device data; communicate the anonymous payment identifier; create a gaming session based on the anonymous payment data, the anonymous payment identifier, and the interactive processing device data; communicate gaming session data; the interactive payment controller constructed to: receive a value bearing item; communicate TITO data and anonymous payment identifier; the payment controller constructed to: communicate TITO data, anonymous payment data and anonymous payment identifier.