How do I squeeze one object through another?

[Adam Trachtenberg]

The Bulge Deformer would probably work well for that.

[Chad Demoss]

I want the object going through the window to be constrained within the frame of the window so that it doesn’t intersect into the geometry of the window frame like a “soft body” I just cant figure out how to get the soft body to work in any direction but on the Y axis.