Multiple Item Pricing

Wondering if this is possible.  We sell Item A in multiple sections of our website and we stock this item in our inventory.  If a new customer purchases Item A in a certain category we want to charge X amount however, if a new customer purchases Item A in addition to other items we want to charge a different amount.
The trick is this: we need this to work for new customers in the webstore so assigning price levels to certain customers won't work and we can't simply create a separate inventory item since we need to fulfill from our inventory.  We also display multiple items on one page and send them all to the cart with one click.  We need to somehow show a different item price based on a defined criteria (site category, custom field, etc.)