My girlfriend and I are both 22, We were both virgins until May of last year, 2011. Of course the first couple times we had sex it wasn't the best because she was very tight and I am apparently much thicker than average. Since then we haven't had sex very many times... Probably 15 max. Ever since we started having sex she hasn't really loosened up very much, it is a little better than when we first started, however I think this may be due to the lack of practice or the amount of time between each time we have sex which is normally about a week or 2. I do not have any piercing on my penis or anything that would cause more pain. Also we use a condom every time.

Ok so this has happened before but nothing nearly this bad... Last night we were flirting all night, I can see she's clearly horny and when we got back to the room we couldn't help ourselves everything was getting very hot. And without some significant foreplay, she was also very wet.
She was on top and began to insert my penis into her... Her face showed complete pain. She said I think were going to need lube and rolled off me. I got up and put lube on the outside of my condom and I got on top in missionary position. Insertion caused no pain this time. I started slow and everything was fine. From her face it seemed that she was getting no enjoyment from it so I started sitting up a bit off her and started going faster. I was getting more enjoyment out of it and all the sudden she grabbed me and pushed me away rolled over in pain...

She said it felt like I was punching her in the vagina. And from what she described it as it seemed like my penis was coming completely out of her and hitting her outside of her vagina before going back in. To me it felt like my penis never came out of her vagina... Any suggestions for us?

First she needs to see a gynecologist... to rule out a number of medial issues. And those are very real. And would exist even if it was a finger. Talking about it is senseless until she's been seen by a medical professional. You can't diagnosie it and neither can we over the interenet beyond recommend she see a doctor to narrow it down to something specific.

Its even possible she has an alergy to latex.

And secondly... if a baby can come out tha hole, its REALLY eleastic... no man ever existed that was even a fraction of that girth. Many guys think they are a lot bigger than they really are.

Of course the first couple times we had sex it wasn't the best because she was very tight and I am apparently much thicker than average.

I have to start with... if I had a nickel for every man who told me he was "apparently" much thicker than average I'd have a lot of nickels. Sorry. Women lie about their age. Men lie about their size.

At any rate if she feels like you are slipping out and you don't realize it you pretty much have to find another position or get a thinner condom.

(Your posts from 2010 and 2009 don't sound like you were a virgin until May 2011. What am I missing?)

She has been checked out by the gyno. Nothing is wrong as far as anything serious. Secondly when I use my finger nothing seems to be wrong. I will try the thinner condom to see if that helps me understand what's going on.

Question about latex allergy, how long would latex have to touch the vagina until it caused pain? I don't know if I'm wording that right, but the pain she has is damn near instantly when a condom is used.

I have a mild latex allergy, and as soon as it comes in contact I know it. But it's not so much of a "punching" feeling as a burning feeling (yes I have been checked by the gyno, and only found out it was an allergy during the exam when the doctor used latex gloves). It could just be the position, try other positions and more lube, but find a non latex based lube.

Avoid the "Natural skin" condoms... they are porous to STDS... (you can never be too sure these days until you've been maried for years). There are non-latex alternatives out there... AND will say on tha package.

And as was mentioned by the ladies, you don't have to be John Holmes to hit many women's cervixes in certain positions... and trust me... they WILL let you know in no uncertain terms because it hurts a great deal.

Simple enough to adust position... and besides you can feel it unless you are numb, once you have done it and know what it was, so there is generally no excuse to do it a second time, much less repeatedly. And it feels like you are bumping something hard about the size of a marble from a guys perspective.