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Stretching an Image

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I'm trying to make a shadow of someone, so I made a copy of the person and blacked it out - however, when I tried to manipulate the shadow to match the angle of the other shadows, I realized that I could only make the image larger, smaller, or rotate it, I can't stretch it - it's keeps it's basic shape.

Is there a way I can stop it from keeping its boxed shape so I can manipulate it more easily?

In other words, I guess I'm trying to figure out if I can anchor parts of a drawing while manipulating the rest.

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