Yes, it's possible, but it depends on several factors. The tip of a pinky, if it is slender, will fit aproximately 1-2 cm into the urethra - if the urethra has already been "broken in" by smaller things graduating to larger. (this scene occurs after the q-tip incident in Punch up) Without "breaking in" this act can be rather painful and is not recommended as a "first time play". As a nurse I've seen catheters as big as large drinking straws inserted into the male urethra. The body can adapt and accommodate to anything, given time. It will also depend on the anatomy of the person receiving and whether or not they enjoy the sensation.
Dawn that was fucking hot ! But I wonder one thing : is this physically possible to enter a finger in urethra ? I know, I'm a pervert ;-)