Teddy Boob Share definition Flag Teddy Boob. Cupping your ladies boob in order to assist in a restless night of sleep. I got hammered last night and crashed at my girls pad . The only thing that helped me sleep was holding on to her Teddy Boob Teddy Boob by spideyskin May 12, 2018 0 0 Get merch Get the Teddy Boob mug. Buy Now — $32.95 See more merch