No, you are correct. The belt passes through the buckle, then turns back on itself with the loose end being held in place by the velcro. Her's one a pic before I've skived (thinned) the leather down to bend tighter to show the belt passing through the buckle.
The keepers should be at each end of the belt as shown in this picture.
The keepers can be tough to get through the "belt loops" on the back of the kilt but you don't have to run the belt through the "belt loops". The general consensus is that the "belt loops" are not intended for the belt anyway even though they are 2.5 - 3". They are intended for your sporran strap to pass through to help hold it up and the larger size is to simply make it easier to pass the strap through behind your back when you can't see what your hands are doing.
I'm assuming this is the belt you purchased
Just to make sure we are on the same "sheet of music":
You will have a good bit of belt turned back on itself. That is the expansion. If you are larger you will have less on the inside, smaller and you will have more on the inside.
The Velcro on these belts are held on by the stitching you see running the length of the belt. The continuous run of velcro also contributes to the stiffness you are experiencing. This is why I leave long space between the to velcro faces so the wearer can easily fold the belt.
You could wet it but I really would not recommend doing that with a belt like this. These belts have a factory finish on them that will prevent water from easily soaking into them as well as if you do soak it, you would need to soak the entire belt (IMHO) to prevent there being a change of appearance in one spot, especially with the embossing.
Your best bet is to sit down and work the spot where you need to bend the leather back and forth to loosen up the fibers. When you get tired of that put it under a stack of heavy books on a smooth flat surface. It will fold tighter over time.
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