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If the file upload is to happen on a regular OWD screen along with other controls and text you can probably do this using a CustomControl.
I wouldn't attempt store the bytes of the file in the session though, write the file bytes to a cache / temp store or whatever and write a handle to the document (e.g. a filename) into the session attribute. Then if the screen submission is a success (i.e. no errors) then commit the associated file to more permanent storage.
I've never tried this - it's and interesting one - might try something out and let you know.
Just wondering if anybody has had any success in adding a File Upload Control?