Multiple Prone Characters in the Same Space?

(look at the plurality of the words used). That's sufficient RAW for me, and passes the Infinite Oregano test.
Agreed. For reference purposes, PHB p.283 semantically denotes a singular ally: "You can end your movement in an ally’s square only if the ally is prone."

By strict RAW, you can end your movement in a square with one prone ally, but not necessarily two. Previously discussed here.
 

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I don't see the problem with several prone creatures in one square. If it becomes ridiculous, impose some arbitrary limit and/or increasingly stiff penalties for lying on top of each other - but sometimes you just can't avoid such a situation arising.

An easy fix is to not permit walking (normally) through a square occupied by two allies. That way, you can have an ally standing over another, and the standing creature can even fall, but then the square is full, and even ally can't walk through it.
 

Agreed. For reference purposes, PHB p.283 semantically denotes a singular ally: "You can end your movement in an ally’s square only if the ally is prone."

By strict RAW, you can end your movement in a square with one prone ally, but not necessarily two. Previously discussed here.

Ally number 1 is prone, so I can enter his square. Ally number 2 is prone so I can enter his square. By strict RAW, them being in the same square does not matter.
 



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