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...."democratic" society simply keeps electing those that enact more and more social benefits? When does this become socialism? Is it possible, if it remains to the vote of the masses, socialism is inevitable - and, as always, followed by its inevitable failure?

You pretty much answered your own question there.. LOL..

Yes, that's one of the reasons america was set up as a "republic"..
Someone back then noted just what you did..
At some point in a democratic state, the people realize tehy can simply "vote" themselves money.. (benefits)
At that point democracy becomes socialism, and the inevitable decline of the society begins..

That was one of the reasons Senators were to be appointed by the legislature of each state, and not elected by the people..
It was also one of the reasons that, while the people elect their state representatives, it is the reps in the house that make the laws, not the people..
The representatives of the people, (house) and the representatives of the states, (senate) were supposed to be a controlling influence on the "mass psychology" of the people's political swings from Liberalism to Conservatism, which historically, at times can become extremist in their moods..
Congress was supposed to be a slow, deliberative body that evened out the swinging pendulum of public opinion and prevented radical solutions to common problems..
Congress is now a "reactive" body, that exhibits no control at all, either politically or fiscally..
Note any similarities to the present political situation ?

"Someone" also noted that democracy is a necessary step in the road to socialism, which is the intermediate step to communism.. ( Marx ? Engles ? Stalin ? )

Anyway, that's my opinion for what it's worth..