Despite the remarkable advances of Large Language Models (LLMs) across diverse cognitive tasks, the rapid enhancement of these capabilities also introduces emergent deceptive behaviors that may induce severe risks in high-stakes deployments. More critically, the characterization of deception across realistic real-world scenarios remains underexplored. To bridge this gap, we establish DeceptionBench, the first benchmark that systematically evaluates how deceptive tendencies manifest across different societal domains, what their intrinsic behavioral patterns are, and how extrinsic factors affect them. Specifically, on the static count, the benchmark encompasses 150 meticulously designed scenarios in five domains, i.e., Economy, Healthcare, Education, Social Interaction, and Entertainment, with over 1,000 samples, providing sufficient empirical foundations for deception analysis. On the intrinsic dimension, we explore whether models exhibit self-interested egoistic tendencies or sycophantic behaviors that prioritize user appeasement. On the extrinsic dimension, we investigate how contextual factors modulate deceptive outputs under neutral conditions, reward-based incentivization, and coercive pressures. Moreover, we incorporate sustained multi-turn interaction loops to construct a more realistic simulation of real-world feedback dynamics. Extensive experiments across LLMs and Large Reasoning Models (LRMs) reveal critical vulnerabilities, particularly amplified deception under reinforcement dynamics, demonstrating that current models lack robust resistance to manipulative contextual cues and the urgent need for advanced safeguards against various deception behaviors. Code and resources are publicly available at https://github.com/Aries-iai/DeceptionBench.