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To make the bread: Heat milk and butter in a medium saucepan over low heat until butter melts. Remove from heat and add warm water. Mixture should be around 110 degrees F (43 degrees C).
Combine 1 cup flour, sugar, anise seed, yeast, and salt in a large bowl. Beat in warm milk mixture, then add eggs and orange zest; beat until well combined. Stir in ½ cup flour and continue adding more flour until dough is soft.
Turn dough out onto a lightly floured surface; knead until smooth and elastic. Place dough into a lightly greased bowl. Cover with plastic wrap and let rise in a warm place until doubled in size, 1 to 2 hours.
Punch dough down and shape into a large round loaf with a round knob on top. Place dough onto a baking sheet; loosely cover with plastic wrap. Let rise in a warm place until just about doubled in size, about 1 hour.
Preheat the oven to 350 degrees F (175 degrees C). Bake in the preheated oven until golden brown, 35 to 45 minutes. Cool slightly before brushing with glaze.
To make the glaze: Combine ¼ cup sugar, orange juice, and orange zest in a small saucepan. Bring to a boil over medium heat and boil for 2 minutes.
Brush glaze over top of warm bread. Sprinkle with 2 tablespoons sugar.