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Dear Sexpert,\nMy question concerns problems I have been having with my girlfriend. She is a virgin, and although we have been trying to have intercourse for some time, we have had no success because she feels terrible pain with any sort of penetration. Sometimes I have penetrated her with my finger while giving her oral sex and she has enjoyed it, but more often than not it simply hurts. Since my penis is larger than my finger, penile penetration has been hopeless. I know from experience that it can hurt the first time for a woman, but this seems unusual. Is it possible that she needs medical attention? Are there any tricks I should know about making penetration as painless as possible? I have had sex with several other women before and have never had this problem, so I'm a little stumped. Pokey\nDear Pokey,\nNo, your girlfriend probably doesn't have a medical problem, but she should see a doctor anyway. Any woman who is (or plans to be) sexually active should see a gynecologist at least once a year. On the off chance that your girlfriend does have a medical condition, the gynecologist will discover it then and can otherwise make sure that everything is in working order.\nSome women do have particularly small vaginas, but even the smallest ones should be able to accommodate a penis. And since you mention that you have already been penetrating her with your fingers, her hymen has probably already been broken. Your girlfriend is probably experiencing "vaginismus," which is basically just a fancy word for the involuntary tightening of the vaginal muscles. This can occur for any number of reasons, not the least of which is nervousness. To minimize this, you need to make sure to move slowly, and try not to pressure her. Make sure she is completely comfortable with the pace at which you are moving.\nAnother primary culprit for pain during sex is lack of sufficient lubrication. Of course, one way to combat this is to extend foreplay until your girlfriend is highly aroused. But some women simply don't produce enough lubrication on their own, no matter how aroused they are. You should experiment with lubricants purchased over-the-counter. Go for water-based ones that won't destroy condoms, such as KY Jelly or Astroglide.\nYou are on the right track by inserting your finger while performing oral sex. Cunnilingus can help contribute to lubrication, and manual stimulation can help her get used to the feeling of vaginal penetration. Next time, try inserting two fingers rather than just one, and see if this also causes pain. As your girlfriend gets used to accommodating more than just one finger, you can try slowly inserting your penis.\nGoing slowly and double-checking your aim are both key. If you move too quickly or are just randomly jabbing at her with your penis, her vagina can get tender and slightly swollen. This will only succeed in making penetration even more difficult and painful the next time you try.\nFinally, try altering your position to allow your girlfriend more control. Many women feel they are better able to control the speed, depth and angle of penetration if they are on top. Ask your girlfriend which position she feels most comfortable in; if she isn't sure, just experiment until youfind something that works. If she prefers to be on the bottom in the basic missionary position, try slipping a pillow under her butt. This can change the angle of entry just enough to make intercourse a little more comfortable.\nSend questions and comments to the Sexpert at jfinkel@indiana.edu.