In a bowl whip the cream until soft peaks begin to form. Add the sugar and cinnamon and whip until it just forms stiff peaks. Place in a decorative bowl.
Place a tortilla on a work surface. Lay 1/2 a banana down the center of the tortilla and top with 1/4 of the chopped chocolate. Paint the edges of the tortilla with water on your finger. Fold the edges tightly toward the center, and seal with toothpicks. Repeat with the remaining tortillas and fillings.
Heat the oil in a deep saute pan to 360 degrees F. Carefully slip the filled tortillas into the oil and cook, turning, until golden brown on all sides, about 3 minutes. Remove and drain on paper towels.
Serve the dessert tortillas with the sweetened whipped cream on the side for dipping.
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