Spinning Teddy hold

Alright ladies, get ready for pain. I am SUPER interested in how to spin a teddy hold. I've seen it a few times from Eva Bembo and some of my other idols, and I just do NOT get it. Where is the grip actually happening? My teddy holds tend to have the hold along the back, and right up against the shoulder in the arm pit. I'm feeling like the grip on this one may be along the inside of the arm, and the side of the body. So, any pointers? Things to focus on, and ways to practice and to work up to it? Does it hurt as much as I think it does? I'll try to find some good example videos.