Never had this problem. I'd rather not have a painful experience.

It happens about 50/50 in cg when the woman grinds down. But just barely. I don't know if it is half the women like it and make it happen and the others avoid it as unpleasant or what. Weirdly, it seems unrelated to body size. Damn women are impossible to figure out.

Also in CG. It actually kinda hurt my tip. It's kinda hard at the end of the road. Not a frequent occurrence though.

I'm not really into anal, but there was a time I did try and I was getting really excited and into it. We were in missionary anal so I could see her pretty face and I thought I might bottom out.  However, I kept going and going until I knocked out a tooth on the way out the top. Technically, it wasn't an internal cum shot when I gave her a facial from her lip to her brow.

You gave her a colonoscopy and a tonsilectomy at the same time....

Very seldom I see someone who I bottom out with. I’m just a little above average in length. But when this happens and I hear the response, it’s never good.

In K9 it’s awesome slapping bottom to my hips, unless they have a shallow well. Please not torture ladies who have shallow wells, unless they want it and let you know.

Knocking the teeth out can’t be pleasurable.