Flossing device according to the present invention comprise a flossing material attachment platform, a handle and a plurality of flossing material attached to the platform. The device is put into the users mouth and chewed thereby compressing the flossing material and producing tooth joint and subgingival penetration. The plurality of flossing material is systematically trimmed to varying lengths creating an interior angle of 90 degrees which automatically positions the flossing material at the optimum angle in relation to the tooth surface. While the device is chewed in the users mouth, the device dislodges bacteria from between teeth, along the side plane of the tooth, as well as the sulcular pocket. In the process this new device also gently stimulates and massages the gum surface promoting blood circulation and the healing properties associated with increased circulation. Because this new device is painless and user friendly, the frequency of use, compared to current flossing devices, is dramatically increased thereby resulting in much healthier and less tender gums.