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I think GP100 got it... the more times a case is fired, the less elastic the brass gets. This equals less spring back, meaning that the shoulder of the case does not spring back as far from the chamber. It's becoming a "press fit" against the shoulder of the chamber. Try setting the shoulder back about a thousandth or two, see if your loaded cartridges don't just slide right in with no resistance on the bolt.
This problem is usually seen in rifles that have more "flex" in the action, such as the T/C Contender. The action flexes just enough during firing to allow the case to form to the chamber without springing back as much. After several firings, the action is a little difficult to close with some brass. Bellm wrote the definitive article about Contender actions and "flex"...
Annealing the neck/shoulder should help somewhat, as well.
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