Modeling fine-grained speaking styles remains challenging for language-speech representation pre-training, as existing speech-text models are typically trained with coarse captions or task-specific supervision, and scalable fine-grained style annotations are unavailable. We present FCaps, a large-scale dataset with fine-grained free-text style descriptions, encompassing 47k hours of speech and 19M fine-grained captions annotated via a novel end-to-end pipeline that directly grounds detailed captions in audio, thereby avoiding the error propagation caused by LLM-based rewriting in existing cascaded pipelines. Evaluations using LLM-as-a-judge demonstrate that our annotations surpass existing cascaded annotations in terms of correctness, coverage, and naturalness. Building on FCaps, we propose CLSP, a contrastive language-speech pre-trained model that integrates global and fine-grained supervision, enabling unified representations across multiple granularities. Extensive experiments demonstrate that CLSP learns fine-grained and multi-granular speech-text representations that perform reliably across global and fine-grained speech-text retrieval, zero-shot paralinguistic classification, and speech style similarity scoring, with strong alignment to human judgments. Code and dataset are publicly available at https://github.com/yfyeung/CLSP.

Evaluating expressive speech remains challenging, as existing methods mainly assess emotional intensity and overlook whether a speech sample is expressively appropriate for its contextual setting. This limitation hinders reliable evaluation of speech systems used in narrative-driven and interactive applications, such as audiobooks and conversational agents. We introduce CEAEval, a Context-rich framework for Evaluating Expressive Appropriateness in speech, which assesses whether a speech sample expressively aligns with the underlying communicative intent implied by its discourse-level narrative context. To support this task, we construct CEAEval-D, the first context-rich speech dataset with real human performances in Mandarin conversational speech, providing narrative descriptions together with fifteen dimensions of human annotations covering expressive attributes and expressive appropriateness. We further develop CEAEval-M, a model that integrates knowledge distillation, planner-based multi-model collaboration, adaptive audio attention bias, and reinforcement learning to perform context-rich expressive appropriateness evaluation. Experiments on a human-annotated test set demonstrate that CEAEval-M substantially outperforms existing speech evaluation and analysis systems.