We have designed and built CalcTutor, an online educational tool for Calculus that employs the Teachers Dilemma methodology. This methodology is centered around a game framework where students take on, and are rewarded for playing well, both the role of learner and teacher. Students create machine-verifiable questions for each other and gain points based on not only correct answers but also asking good questions. This framework has been used and studied in a variety of projects, mostly in the K-12 arena. The CalcTutor tool expands this approach to college level classes, specifically introductory Calculus. In this paper, we are reporting on our experience with a pilot study of CalcTutor, as used in conjunction with a college Calculus class. The system is designed to support learning in two ways, teachers can build quizzes for their students and the students can pair off and play games with each other. The students are given dynamic feedback about how appropriate their question is for their partner in the game as they develop each problem. During this pilot study, students asked and answered problems of two types: finding the derivative of a function and calculating the tangent line to a function at a point. The system was simultaneously tested in five introductory Calculus sections which generated a sizeable body of system data as well as survey feedback. Unfortunately, like many new tools, some of the students found getting used to the interface hard and some of our theoretical concepts did not pan out. Nevertheless the technical parts of the system worked well; students and teachers were able to create and answer questions without any issues. Some of the untested ideas that we were trying out met with success. And many students enjoyed some features of the system, particularly the instantaneous feedback.