I tested the following advice using my Clip Sport with three mp3 audio files.
(I could not get two files to work as you described.)
FOLDER MODE
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Put at least three repeating / shuffling mp3 files in a specific subfolder inside the Music folder.
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Use the Folder Menu to select the specific subfolder.
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Then select one mp3 for immediate play.
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Then press the “Options” menu button (below the oval shaped large button).
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Then select Repeat -> All AND Shuffle -> On
MUSIC MODE
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Make sure all your repeating / shuffling mp3 files have the same “Album” name in the ID3 tags.
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Use the Music menu to select the specific “Album” name.
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Then select one mp3 for immediate play.
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Then press the “Options” menu button (below the oval shaped large button).
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Then select Repeat -> All AND Shuffle -> On
BONUS IDEAS
Maybe create a short “silent” mp3 file (with the specific “Album” in the ID3 tag) to be your audio file #3 ??
OR, Maybe put two copies of each of the two mp3 files into the specific subfolder, as described above.