My dad likes to make jokes of this sort and one of his favorite sayings is,

"It's not the size of the want, but the magic of the magician that counts."

I think it depends on the size of the woman. Women are different sizes inside too. Some are long and some are shorter.

As long as you both can feel what's going on and nobody is getting rubbed raw from it being too tight, then I don't think it matters.

I would well imagine that for anal it would. Tried it once, not going there again. Unless his penis can get a lot smaller and start to vibrate and not move while it's there, it's not happening again. lol.