The girl:

She's a 8-9, amazing personality, mature, and very very smart. She's basically everything I could ever want in a girl. We were set up through a friend and after the first date things just started to snowball emotionally and now we're both really invested in eachother. However, for some reason we held off on sex until now, which is fine by me because she's great in bed otherwise and I enjoy just hanging out with her. I know this is kindof an AFC thing, but *I* made it very clear that I wanted to take things slow because of the connection we have.

The problem:
So we get to the sex part. Everything's going good, she's turned on, I'm turned on, etc. Then I go to finish the deal and it's like trying to shove a cucumber into soda bottle. It just doesn't want to go in. She's told me her first bf didn't have a problem, but ever since that she's been doing a lot of running (like 5-6 mi every day) and every guy she's met after her first had the same problem, and they usually leave after they attempt and fail at sex. I asked her about the size and she says I'm about the same as her first bf, and the other guys were smaller. Which doesn't make much sense, but why would she lie?

Anyway, I told her that I wasn't going to give up on her and we're going to hang out again. But I have no idea how to get past this... different lube? Technique? no idea. I really don't want to give up on her, and I can't find anything in the literature about a girl's pussy being "too tight" (I guess nobody's encountered this problem before.. go figure)

SO yeah, thanks for reading.

_________________
The question is not whether you will be set up for failure; but instead whether you will choose to accept it.

Wow! Thanks so much King! Yeah I dug around on wikipedia and found this:
http://en.wikipedia.org/wiki/Vaginismus
Which describes it almost perfectly. Even in the "emotional experiences" section:
That's basically word for word what she was telling me, about how she was "defective" etc. Glad I found this so I can show her and hopefully things will work out after all.

_________________
The question is not whether you will be set up for failure; but instead whether you will choose to accept it.

I think she got a rare case but why not seek medical expert or someone knows what happen with her.

Isn't this called vaginismus or something? Where the vagina is small. I had a girlfriend where we struggled to get it in. She never told me why she was so tight so I have no real idea what was going on. But sometimes it would take A LOT of effort to get things started. If she was on top, sometimes we couldn't get it in at all.

One thing that helped us was escalating a little slower. Start by using your fingers to warm her up. Start with one finger, then two. Don't focus so much on pleasuring her while doing this but more about massaging the muscles and getting her to expand while widening your fingers more and more.

Good luck