We demonstrate that the extrusion speed of thermoplastic urethane elastomer can modify its optical transmission by a factor of more than 100. Varying extrusion speed at constant temperature may tune optical properties along the axis of a filament, for example creating absorbent regions that are sensitive to length and diameter changes, surrounded by more transmissive segments that carry the sensor signal over long distances. Such waveguiding in a stretchable optical fiber requires a stretchable cladding with lower refractive index than the core. In experiments toward a rugged, stretchable fiber cladding, we investigated whether solvents could modify the outer structure of the filaments. Soaking the filaments in NMP (n-methyl-2-pyrrolidone), then stretching the filaments while the solvent dried, turned out to modify the filaments in a way that solvents alone did not, creating porosity and reducing the appearance of optical clarity.