Posting photos into messages feels more like a workaround than a method. Basically the image file itself has to be somewhere publicly accessible on the Web then you need to paste the Web address of the image into your post but surrounded by the correct UBB tags.
The easiest way of doing this without all the tedious understanding of arcane coding is to go to
tm-img (this links to the instruction page) which is an image hosting site set up and run by denizens of this forum. If you set up an account you can upload photos then there is an option to copy the full image UBB code and paste it into your TM post (without using the insert image button) which should put your photos directly into the post. Clicking on the preview button is always worthwhile to check that things have actually worked.
Hope this helps.