Cutaneous leiomyomas are known to arise from three locations viz, arrector pili muscle, dartos muscle in the scrotal sac, and smooth muscle layer of blood vessels. Cutaneous piloleiomyoma (arising from arrector pili) is an uncommon benign skin tumor presenting clinically as a single or numerous painful nodules. They can either appear diffuse or zosteriform/segmental in rare cases. We report an unusual case of multiple tender papulonodular lesions on the right infrascapular region. Histology from one of the nodules showed a dermal tumor consisting of interlacing fascicles of spindle cells, consistent with the diagnosis of piloleiomyoma. We prescribed our patient with oral calcium channel blocker, amlodipine, to provide symptomatic relief from pain and which can be considered used it to treat similar cases.