Abstract: A tarpaulin fastening device includes a support frame for support of one or more winch/spool assemblies and associated interconnecting line cord while being removably attached to a flat bed trailer using compression. The interconnecting line cord is extracted/retracted from/to its respective winch/spool assembly through a keeper mechanism. The interconnecting line cord is woven through eyelets of one or more connection pins and terminated with an anchoring mechanism. Once extracted from the winch/spool assembly, the interconnecting line cord is anchored to a flatbed trailer using the anchor mechanism and each connection pin is alternatingly connected to connection points along a length of tarp covering a payload supported by the flatbed and to connection points along a length of the flatbed trailer. Once the interconnecting line cord is anchored and connected to the tarp and flatbed, the tarp is secured onto the payload by actuation of the gear assembly.