Look at the silver film rollers. Are they level? Are the frames of the shots square to the film, or slightly canted? If one of the rollers is not level it will cause the film to wind at an angle and bind.
When you start the film, put light pressure on the film roll as you wind forward to the start mark, using a finger or two. This will keep the film taut as you wind, even though it will move up a bit and relax as you go to close the back. I am basing this partly on my experience of loose winding on a Fuji GS690, which leads to just what you describe. I can't remember having this happen with a TLR.