Wordpress cached image issue - wordpress

I am having an issue with image caching I believe. Not 100% sure thats the issue, but perhaps someone with greater expertise could assist.
In my wordpress site, I have some images that were uploaded via the media library. Now, when I first enter the site that has no cached info from the site, the images load and display properly. But, when the site has been cached, the images are loaded, but are not displaying on every reload.
The reason I know is, because when I do a hard refresh (Shift + F5), where I am reloading the site from square one, I get the images to display properly again.
Any reason why this might be happening? I am completely lost, and don't know where I could start to fix this problem.
Thanks,
Andy

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http://afinderskeeper.com/
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I am just a random stranger on the internet, but I have to thank you guys! Your solution fixed a problem on my site that has bugged me for ages!

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