How to say roy looked solemn as i told him the story. in Japanese

1)そのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location悪い悪い(warui) (adj-i) hateful/abominable/poor-looking/detestable/amazing/fantastic/admirable/lovely/wonderful知らせ知らせ(shirase) (n) notice/notificationを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,話し話し(hanashi) (io) talk/speech/chat/story/conversation/discussions/negotiation/argumentた(ta) (aux-v) indicate past completed or action/indicates light imperative時(toki) (n) time/hour/moment/occasion/case/chance/opportunity/season/the times/the age/the day/tense、(、) Japanese commaロイno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighまじめまじめ(majime) (ateji) diligent/serious/honest/sober/grave/earnest/steadyな(na) (prt) connects adj to noun/indicates emotion or emphasis/command/prohibition顔(kao) (n) face/visage/look/expression/countenance/honor/honour/face/influence/notorietyつきつき(tsuki) (ok) deskを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,したした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
sono warui shirase wo hanashi ta toki 、 roi hamajimena kao tsukiwoshita 。
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