Try to get some blood in your glans before putting on the extender, a 20% erection will help.
Jelking first will also help, and less traction will help. Also try talkum.
Dont give up, it takes a lot of hours to get used to wearing it. I also had problems with turtleing when removing it, but now it feels like my penis have given up to the stretch, so it hangs nice when I remove it.