Thats area is very wimpy, I had an atv in the back of mine and the front was touching that same area an just from braking it bent the bed into the cab...

 

The best way would be to pull the box off. You will need room to straighten it out. You can then also touch up the cab properly.

 

^x2 They just don't make these trucks like they used to anymore...The only way to fix it right is to pull the box. Disconnect your fuel filler neck / vent tube and pull your brake lights first. This way you can address any issues with the cab, and have the room to pull the back of the bed out. Its not gonna be perfect but better than it is.

 

if its less than a 2-3 thousand, i personally would not recommend using your insurance to fix it. I heard on Clark Howard that its best to pay for this sort of thing out of pocket, not only do you pay your deductible (average 500, though could be more or less), your rates go up for YEARS, by the time you are done paying all that, you payed the amount of the repair unfortunately...sadly, its best to only use it, again, only IMO, for catastrophic or bigtime fixes, this, i would find a way to pay out of pocket myself...

 

The good news is you can pull most of that out... You also should be able to prime and touch up the area with fresh paint without it being highly visible.