Expressiveness is central to speech-to-speech translation (S2ST), yet existing datasets rarely align source and target speech jointly in content, prosody, timing, and speaker identity. Consequently, current systems often rely on indirect conditioning or transfer mechanisms. To obtain this supervision, we introduce a training-data construction strategy that combines professional dubbing, which provides human-performed correspondence in content, prosody, and timing, with multilingual voice conversion to reduce speaker mismatch. We evaluate this supervision using existing expressive S2ST systems and DirectS2ST, an end-to-end method developed in this work that predicts the complete target-speech representation directly from source speech. Experiments on English-German and English-Spanish show that holistic parallel supervision improves expressive realization across all evaluated systems. DirectS2ST exhibits the largest gains in content, prosody, timing, speaker similarity, and human-rated expressiveness. To our knowledge, this work provides the first systematic investigation of holistic parallel supervision for expressive S2ST.

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