You could select the (nCloth) wrapper border cvs then create a transform constraint. Make the constraint strength low and turn off gravity. Now run interactive playback and translate the constraint across the lollipop( a passive nRigid ) pulling the rapper onto the lollipop. Then scale the constraint down( perhaps even a negative scale ) to pull the wrapper together. You can then set initial state on the cloth and delete the transform constraint. For it to work well your wrapper should be fairly detailed and have full surface self collision with no bend stiffness and low thickness. Increasing the substeps will also help it handle the self collisions.
If instead you wished to see the process as animation then just keyframe the constraint instead of running interactive playback.
Duncan