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Tint 1/2 of cookie dough blue, 1/4 light copper and/or brown and a small portion yellow; reserve remaining dough.
Cut ten 3 x 3 in. pool side squares from blue dough. Using circle cutter and yellow dough, cut out sun.
Using boy cutter, cut out 8 children (make extras to allow for breakage). Thin reserved dough with water to a piping consistency.
Tint small amounts of thinned dough yellow, brown, black, orange, green, red, violet, pink and copper. Pipe tip 2 hair and bathing suits.
Add tip 1 eyes, noses, hair bows and mouths. Bake cookies.
Wrap craft block with foil. Position on foil-covered board. Use royal icing to attach cookie squares to pool sides and striped candy sticks between each square.
Cut and attach lollipop sticks in various sizes to backs of children with royal icing.
Attach 8 in. lollipop stick to back of sun cookie with royal icing; attach candy corn "rays" with royal icing.
Crumple pieces of blue plastic wrap and position in pool for water. Insert children and sun cookies in pool.
Sprinkle granulated brown sugar around pool base. Attach striped gum and hollow-center round candies to top pool edge with royal icing.