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If your custom device uses one BULK-OUT and one BULK-IN endpoints for the fundamental I/O communication (except for the CONTROL endpoint for standard/vendor requests), you can utilize NI-VISA's RAW session in your PC-side app (such as LabVIEW). The step-by-step procedure for this is found in the link that Dennis provided. In this case you don't have to write any kernel mode USB driver and its wrapper DLL.
If the vendor of USB chip that your device is using supports some VCP (Virtual COM port) driver that allows you to use it as if it was a serial device, you may be able to use any serial (RS232) port approach. In this case, your app will access a virtual serial COM port.
If you are going to write kernel-mode USB driver from scratch, you will need Microsoft Windows DDK and a C compiler (such as Visual C++). However writing kernel mode driver is very hard for beginners.