I am 65 and am now seeing an old high school girlfriend. She's been widowed twice and hasn't been sexually active since her second husband died, over three years ago. She says the Lord must be punishing her to take away two husbands. She says her last husband is still around and will return, and even keeps his clothes in her closet. We cuddle and sleep with each other but both times I tried to have sex with her, she claimed that I hurt her too much. She says it's because I'm too big and she hasn't been sexually active in a while. Could her vagina really have shrunk or is this just a ploy?

There are several explanations for what is happening here. One is that she has not mourned the passing of her husband. That she still has his clothes around and expects him to come back is certainly an indication of that. If that is the case, there is very little that you can do other than can continue to be her friend, because if she is not open to a new sexual relationship, then she will not lubricate and intercourse will be painful.

Of course it could also be that because of her age there might have been some atrophying of her vaginal muscle and natural lessening of lubrication, which would also cause the pain. If she really wants to have sex with you and is willing to use a lubricant, then that might be the solution.

If the size of your penis is the problem, then there are certain positions that can be used where even a large penis won't cause pain such as the side-by-side or posterior position.

Talk to her and try to discover what the real source of the problem is. If it turns out that she is still mourning her husband, then you can continue to have a good time together, and maybe even cuddle, but do not try to continue to have a sexual relationship together.