My girlfriend is 31 years old and is still a virgin. We have reached a point in our relationship where she wants to have sexual intercourse. However, from the stories she has heard from her friends, the first time always hurts and she would not enjoy it. As a result she has this fear in the back of her mind now.

We do a lot of fore play. She wanted me to prepare her for sexual intercourse. I first tried inserting my middle finger in her vagina until she feels comfortable with it and then after 2 weeks I inserted 2 fingers let her adjust to that. I have purchased 2 different 5 inch vibrators one with a 1 inch girth and the other with 1 1/4 inch girth. I have already used the 1 inch girth vibrator with a lubricant. I am able to put in 3/4 of the vibrator inside her vagina. She feels a slight pain and tightness. However, the next time we had fore play I was only able to put 1/4 inch in and further because she was able to feel the pain. My girlfriend feels frustrated that her vagina will never adjust. Is there any thing me and my girlfriend can do to make her first time an enjoyable and pleasurable one? Plus, am I preparing her the right way?

First of all I want to congratulate you for being so considerate, caring and resourceful. She is very lucky to have found you. The only “mistake” you are making, and this applies to both of you, is to put so much emphasis on the first time you have intercourse. What if she does experience a little pain the first time and it is not so great? As long as after a few more tries you both learn to please each other and you go on to have years of great sex, will it really matter that the first time wasn’t special? By putting so much emphasis on the first time, you are both going to be so nervous that I doubt that it could ever be very erotic, and that’s all right. 

My advice is to go ahead and see what happens, and then work towards becoming great lovers. Do use a lot of lubrication that first time, and if she puts a pillow under her behind, that will change the angle of intromission, making it a little easier. 

If she is so nervous that she involuntarily clamps shut her vaginal muscles, then you might want to restart the process you have already engaged in, trying to get her to open up to larger and larger objects. But hopefully this won’t be necessary.