You need to write a .inf file for Windows that ties up your device VID and PID with the system usbser.sys. Mine looks like this (Replace YourCompany as necessary, put in your VID and PID (in hex), and change the DriverVer line to whatever date and version you want):
; -----------------------------------------------------------------------------
; XP/2000 USB Comms Port Setup
; -----------------------------------------------------------------------------
[Version]
DriverVer=12/03/2008,1.0.0000.0000
Signature="$Windows NT$"
Class=Ports
ClassGUID={4d36e978-e325-11ce-bfc1-08002be10318}
Provider=%YourCompany%
[DestinationDirs]
DefaultDestDir=10,system32\drivers
DriverCopyFiles=12
[ControlFlags]
ExcludeFromSelect = *
[Manufacturer]
%YourCOmpany%=YourCompanySerialPort
[YourCompanySerialPort]
%YourCompanyUSBSerialPort%=YOURCOMPANYUSB,USB\VID_1234&PID_ABCD
;
; Win 2000/XP
;
[YOURCOMPANYUSB]
Include=mdmcpq.inf
CopyFiles=FakeModemCopyFileSection
[YOURCOMPANYUSB.HW]
AddReg=YOURCOMPANYUSBAddReg.HW
[YOURCOMPANYUSBAddReg.HW]
HKR,,DevLoader,0,*ntkern
HKR,,NTMPDriver,,"usbser.sys"
[YOURCOMPANYUSB.Services]
AddService=usbser, 0x00000002, FuncDrv_Service_Inst
[FuncDrv_Service_Inst]
DisplayName=%USBFilterString%
ServiceType= 1
StartType = 3
ErrorControl = 0
ServiceBinary = %12%\usbser.sys
[Strings]
YourCompany="YourCompany"
YourCompanySerialPort="Your Company USB Serial Port"
USBFilterString = "USB Serial Service"
Note this works with 32 bit OSs only. It also works with Vista although the file header doesn't say so!
Be aware that some versions of usbser.sys have significant problems, including bluescreening, for example when transferring packets that are exact multiples of 64 bytes. If you're using XP SP2 or previous then install hotfix KB943198. XP SP3 and Vista are fine.
For the Mac you simply need to report your device class correctly and the driver scan picks up the correct drivers. (Windows ignores the device class which is why you need to supply the .inf file).
EDIT: Sorry, I should have been clearer. This will not fail to enumerate if it can't draw the full load - I'm not sure that's possible.