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In this paper we propose a novel methodology for analyzing web user behavior based on session simulation by using an Ant Colony Optimization algorithm which incorporates usage, structure and content data originating from a real web site. In the first place, artificial ants learn from a clustered web user session set through the modification of a text preference vector. Then, trained ants are released through a web graph and the generated artificial sessions are compared with real usage. The main result is that the proposed model explains approximately 80% of real usage in terms of a predefined similarity measure.