Sorry. This can not be done with standard layers - pixel or vector.
Once a pixel or vector object has been transformed (rotated) and that transformation has been committed, the bounding area has been reset. There is no feature or method to make the bounding box remain or reset to the original object prior the transformation.
Smart objects do remember rotation amounts. So you the bounding box remains tied to the overall shape in smart objects and will be seen as rotated if you later want to transform again.