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Cut 3 1/2 in. circle for propeller from black posterboard; cut 2 in. semi-circle windshield from silver posterboard. Using royal icing, pipe tip 4 circular motion lines on propeller; gently bend windshield. Set aside.
Ice 1-layer sheet cake smooth. Cut 5 hidden pillars to 3 in. long and insert into sheet cake to support plane.
Trim bottom end of cross cake to a point to resemble plane's tail and cut hole for seat area. Place plane cake on board cut 1 in. larger than cake.
Ice sides of wings smooth in blue. Position cake on pillars. Insert lollipop sticks into both sides of tail, leaving about 2 in. extending; attach cookies, cut in half, to lollipop sticks with icing, attach center cookie half to cake with icing.
Trace plane details with toothpick, then outlline with tip 4. Cover seat area with tip 4 zigzags; position groomsman. Pipe tip 3 uniform, goggles and helmet on groomsman.
Cover plane with tip 17 stars. Attach propeller with icing and insert windshield. Print tip 3 message.
Pipe tip 21 zigzag puff clouds around plane and for top and bottom border of sheet cake.
(Note: Combine Lemon Yellow and Golden Yellow to achieve airplane shade.)