With a very well endowed man intercourse usually does hurt at first even if he is fairly gentle. That changes after a woman gets used to a larger size.
But for my 'dating' - hubby and I would have never had kids as he was sterile from the get go. I did not know he was sterile at the time. That came out later. After a few frustrating years I finally got pregnant, four months after my first affair.
No set frequency. It varies a lot. Often happens when I am away on my business trips and conferences. On occasion I date locally. Hubby and I have separate bedrooms now.