After you upload it the first time can you go to the page and do a hard refresh and see the image? Have you checked the images folder to see if the image is getting uploaded correctly the first time though?
The image should be uploaded the first time, if you go to any page that should be showing the image like the details page in the admin area then try refreshing the page to see if you can get the image to show up. If you can confirm that it is not uploading the images until the second time you do it let us know so we can look into this further with you.