When making a shape out of a photo. Right click on top of the photo and choose Aspect Ratio, then make the photo a Square. Then use the Photo tab and choose Mat, and select Cut Outs. Choose your shape. If you cut out photos this way, you will not have to flatten the photos.
If you are doing multiple photos on a page with the same shape, copy and paste the original shaped photo, as many times as you want to add a new photo. This will maintain the same size and features on each shape. Then drag your new photo into the copied Shape.
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