I'm also somewhere between 8" and 9", and have experienced some women who become reluctant at the sight of it. If they're truly scared, it's best not to....uh press them...but I've found that a little humour and a lot of gentleness can do a lot to convert their fear into admiration and even more. When she's small, let her control the rhythm and it'll be fine. Obviously, if you have a big dick, she's 5'1" and you want to start by slamming her, you're going to cause pain.
Reminds me of a session I had with Slave Gwen. Yes, I'm dating myself again, but do any of you remember her? She was a schoolgirl kilt-wearing submissive who used to ask to be pushed to extremes. I absolutely loved her bbbj because she would really go deep, and she wasn't a big girl. I know I was definitely one of her more vanilla customers cuz all I went for was straight-up sex and facefucking. Once I met her for a session at a hotel on Yonge and decided to try anal for the first time--a specialty of hers. I stood by the bed as she got on top of it on all fours and when she felt the head of my dick, she rather suddenly and forcefully backed onto it hard. I'll never forget that feeling and her scream. Fuck. Pulling your dick out of a girl and seeing blood on it is always traumatic, and for a second I panicked like a true coward, thinking the condom had burst and that the blood was mine, but it was hers. She was crying and running for the bathroom and I was torn between seeing if she was alright and cleaning myself off. I asked if there was anything I could do, and then there's a fucking knock on the hotel room door. I tell you, I was shitting myself, but in the next moment Gwen came out and said it was her friend, come to help her go to the doctor. I had never realized how much she was into the submissive scene and to this day I don't know if it was an act, but she came back to me, said she'd been a bad girl and that I didn't have to pay for that session, but would I promise to see her again when she was better? Weird, I know, but that was Gwen all over. I wonder whatever happened to her.