This tutorial demonstrates how to create the effect that a pin has been pierced through paper in Digital Image Suite 2006. The instructions should be similar for versions of DIP 7 and up.
Open the pin and place it on the paper where you wish for it to pierce through

Choose the Marquee tool and draw out a square that covers the pin, Use Adjust Marquee to create a more rectangular shape and rotate it if required.

Select Edit> Duplicate (or CTRL+D) to duplicate the section. The duplicate section should be covering the pin.
With the duplicate piece selected, choose Touchup > Other Photo Repair> Dodge and Burn Brush
Choose a brush of appropriate size, a soft edged brush and reduce the brightness to between -5 and -20. The strength depends on the color of the paper you are working with.
Use the brush to paint just to either the left or right of where the pin continues under the paper.
Click done when happy with the result.
Select the background paper in the stack and again choose Touchup > Other Photo Repair> Dodge and Burn Brush. Reduce the brush size and brush over the pin to affect the background underneath at either end where it is overlapped.
With the top piece selected again, choose Effects> Transparency > Transparency Brush and with a small brush set at around 98% transparency make the edges a little jagged. Click Done
Choose Touchup > Other Photo Repair> Dodge and Burn Brush. Reduce the brush size and a brightness of around -5 or less, brush just over the jagged edges.
The final result should be similar to that shown below
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