Wisconsin Windmill Share definition Flag When a man is having sex with a woman and is about to cum, he does the helicopter with his dick while he is cumming. My boyfriend did a Wisconsin Windmill last night. It's gonna take ages to clean up. Wisconsin Windmill by GHAC August 21, 2013 0 0 Get merch Get the Wisconsin Windmill mug. Buy Now — $32.95 See more merch