Technically it should be possible when both drives never use more power than the USB port can supply.
However most 2½ inch drives seem to draw around 500 to 600 mA, which is more than a single USB 2 port can supply. Using only a single, extra low power drive or two USB ports *1 to supply power is the normal solution. Anything else required an external PSU.
This made it unattractive to build a dual 2½ disk enclosure. Those would require an external PSU, competing with external 3½ inch disk enclosures. And the larger disk enclosure used to be faster and larger.*2
Still, there is no technical reason why one could not build a dual 2½ inch disk enclosure. Especially not with the 900mA limit from USB3. It is just that it would serve a very small niche market. And that makes it commercially unattractive.
*1 IIRC using dual USB ports to supply more than 500mA power is not even officially allowed by the USB standard.
*2 Also, it is possible to use a 2½ SATA disk in a 3½ inch disk enclosure. Thus further reducing the market for it.