LLM-based annotation has advanced rapidly, yet existing benchmarks remain misaligned with real-world practice. Actual annotation often involves lengthy, task-specific guidelines, and different annotators may produce divergent but reasonable judgments, especially on boundary cases, where single-labeled dataset fail to reflect this disagreement. This gap also limits existing single-agent and workflow-based annotation systems, which often lack adaptability to complex, evolving guidelines. To bridge this gap, we introduce ANT-A Benchmark, a real-world multi-annotator benchmark spanning 7 datasets across domains and modalities, with task-specific guidelines and 5 independent human labels per instance. ANT-A enables a distribution-aware evaluation, using Fleiss’ 𝜅 to assess how closely model annotations align with human labeling distributions. We further propose ANT-OR, a multi-agent annotation framework that refines prompts by distilling contrastive decision rules from positive and negative feedback. Experiments show that ANT-OR improves agreement@≥2 accuracy by 4.5 points over the strongest baseline and achieves the highest alignment with human annotator distributions as measured by Fleiss’ 𝜅 within 2 points. Code and benchmark are available at https://github.com/Krueske/ANT-OR.