If $B$ is a set ordered (partially or fully) under $S$ then $S=S^2$?
Intuitively this seems right.
We know according to the definition of ordered sets that $S$ is reflexive, antisymmetric and transitive.
Let $S=I_B\cup R$ where $I_B$ is the identity relation over $B$ and $R=S-I_B$. Then $R$ is of form $\{(a,b), (b,c), (a,c)\}$ and $R\cdot I_B = R$ so $R\subseteq S$ and therefore $S=S^2$.
I know something lacks in my proof but I can't think of another way to prove this.
Your proof lacks generality - $R$ can have more (or less) than three elements.
Transitivity of $S$ is equivalent to $S\cdot S\subseteq S$. On the other hand, reflexivity means $I_B\subseteq S$, hence $S=I_B\cdot S\subseteq S\cdot S$.