My company uses a software that needs an "original" USB drive inserted, but that's an old software, and currently we only have 1 working pen left. Is there any way to create an image of the pen, or something like that so we can have the software on 2 of our PC's?
Are you sure this is a USB mass storage device and not a security key?
Security keys can be duplicated but it requires intimate knowledge of the controller chip and likely is in violation of any license you're using the software with.
If this is truly a USB flash drive, with no other additional devices (USB devices can present themselves as multiple devices to Windows, so open Device Manager and watch for new devices) - try to find a device of the same exact make and model and use an imaging utility such as dd for windows or similar to copy it on the sector level. At the very least try to make sure it's the same capacity.