First of all we all estimate which is a bad idea. Get the ruler out and see exactly what size he is. Also, if you don't want to do that measure with your hand and then use the ruler against your hand to estimate. Basically, if a guy is under 5" that is small this is really for girls that think then have a 10" its probably 8" just looks like 10"

jkmcnamara, I have the same condition and use the dilators. They are VERY helpful

I was extremely small... so small I couldn't use tampons. However, the gynecologist suggested dilators. It was frustrating at first because it hurt a lot but the more I kept using the dilators- the bigger I became. I am now able to have sex! Just be patient, it took me about 3 months before I could have sex with my husband.

My husband and I just celebrated our first anniversary, and we were also virgins when we married. My mother's best advise to me was to keep a little bottle of KY jelly. Especially at first, it really helped me since I had trouble relaxing enough on my own to fit my large husband. It was frustrating for me at times, because I wanted to be an instant expert and always find it satisfying. Btw, painful sex is not normal. I got a UTI during our honeymoon from spermicide, and it took me way too long to figure out I needed to see a doctor because I thought it would just hurt sometimes. Like the other women said, it doesn't always get better with practice. You may need to see a doctor who can find the source of the pain.