Let $G$ be a finite transitive group on a set $Ω$, let $α\in Ω$ and let $G_α$ be the stabilizer of the point $α$ in $G$. In this paper, we are interested in the proportion $$\frac{|\{ω\in Ω\mid ω\textrm{ lies in a }G_α\textrm{-orbit of cardinality at most two}\}|}{|Ω|},$$ that is, the proportion of elements of $Ω$ lying in a suborbit of cardinality at most two. We show that, if this proportion is greater than $5/6$, then each element of $Ω$ lies in a suborbit of cardinality at most two and hence $G$ is classified by a result of Bergman and Lenstra. We also classify the permutation groups attaining the bound $5/6$. We use these results to answer a question concerning the enumeration of Cayley graphs. Given a transitive group $G$ containing a regular subgroup $R$, we determine an upper bound on the number of Cayley graphs on $R$ containing $G$ in their automorphism groups.