Let's restrict attention to the case where the components of $S - \Lambda$ are all discs (with three or more cusps).  Following Thurston, we choose singular foliations of these discs, with the foliations being horocyclical in the cusps of the disks.  These foliations-of-discs fit together to give a foliation $F$ on $S$.  Note that $F$ is transverse to $\Lambda$.  (If you arrange matters carefully, you can ensure that $F$ contains your loop $I$.)  We now collapse all leaf segments of $F - \Lambda$.  It is a (difficult) exercise to check that the quotient $S /{\sim}$ of $S$ is again a surface and is in fact homeomorphic to $S$.  Also, the lamination $\Lambda$ descends to give a foliation $\Lambda/{\sim}$ in $S /{\sim}$.  The spaces of transverse measures on $\Lambda$ and on $\Lambda/{\sim}$ are naturally isomorphic.