My girlfriend told me that she feels that I'm to big for her. I suppose it should be a compliment but it isn't. Its always been a problem in my life and I really want things to work out. She says sometimes it hurts but sometimes it doesn't. There's hope! My question is: Is there anything you would recommend to remedy our problem or any information the discusses this situation you could recommend?
My best advice for a situation like this is to focus on positioning. Certain positions can allow for deeper penetration, which may be what causes your partner discomfort. Other positions prevent very deep penetration, and these are the positions that you and your partner may want to focus on. Some positions I would suggest are girl on top, where she is laying down on you with her legs together. In this position, penetration is controlled more by her, and your entire shaft receives stimulation. You can also try having sex in the spooning position. This position also tends to limit penetration while allowing for stimulation all down the entire cock. There are plenty of other positions for you and your partner to try out, so I would suggest looking into a positions book, including Kama Sutra positions. We have one at the shop right now called The Bedside Kama Sutra that has great pictures of all the positions as well as descriptions of how to get into them.
Another thing to consider is arousal level. As a woman gets aroused, her uterus lifts, elongating her vaginal canal. If you take a long time to get your partner aroused, her vaginal canal will be able to accommodate more of your cock more comfortably. Take your time with her and your patience will pay off.