how to dynamically add images to multiple pages by the class name

Hi I have an issue

I am currently adding images to the page new on this sample website but some images I would like to add to the various catagory pages such as new in, crop circles or childrens without having to upload to the different pages seperatley.

Is there a way to dynamically add the images to other relevant pages depending on the class of the image without having to upload to each page individually using phph or ajax which would take lots of time.

or is there a plugin where I can add images to multiple pages at once?

I figure this is an ajax issue but am hoping there is a wordpress solution.

It would be fab if anyone can help.

here is the url

http://satbulsara.com/luke-irwin/?page_id=175