37M here in a long distance relationship. So we get\[28f\] to meet only once every couple of months. We always need lube for smooth entry. And almost every time we do it without a condom meaning i just pull it out before ejaculation. I want to try it with a condom because i do not want to be aware of the point of no return and still feel safe.
If we try it with the condom on, i am unable to penetrate and she is feeling the pain upon my trials to enter. Can you suggest me what to do?