Manual annotation remains a major bottleneck in ultrasound (US) bone segmentation, where experts typically iteratively refine rough brush masks rather than delineating precise contours in a single pass. We present ExiL, a mask-conditioned progressive learning framework that models annotation as a structured refinement trajectory. ExiL combines a synthetic expert-like brush simulator based on signed distance fields with a lightweight 7.8M-parameter U-Net that learns to complete and refine imperfect masks from US images. During deployment, an expert mode updates the model directly from accepted refinements, enabling continual adaptation to expert behavior. Evaluated using UltraBones100k cadaver data for quantitative segmentation and a prospective volunteer dataset for annotation-efficiency analysis, ExiL reduced single-expert average annotation time from 60 to 20 seconds per frame (66.7\%) and improved mean Dice by approximately 0.045 over non-progressive training, while achieving 0.87 Dice and 2.7 px boundary error in the best trajectory-aware setting. With 10--50 ms inference, ExiL enables real-time, self-improving annotation for US-guided orthopedic workflows in practical clinical labeling.

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