Demon King from Today!
The Chain of Love and Fate (1x12)
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Yuri goes to see a dolphin show, but when he is called up to the stage to shake hands with a dolphin he is then transported to the other world. After Yuri finds out about an imposter thought to be the Demon King, Yuri plans a trip to save the person, accompanied by Wolfram and Conrad. Along the way they met up with Gwendal. During the trip, they encounter a Sand Bear and Wolfram along with the rest of the soldiers except for Conrad and Gwendal fall into its sand trap. Yuri orders Conrad to rescue Wolfram. Gwendal and Yuri continue on to the country of Svelera. When Gwendal and Yuri stop at a town to gather water and provisions, they are mistaken to be an eloping couple and are chained together. They manage to escape.