Having sex with a virgin

I started seeing this woman a few months ago, and we started hooking up. We have done everything, except have sex and she wants to. She is a 26 year old virgin, and we've already tried having sex once but couldn't. I don't think she realized it is going to hurt, but she said she still wants to again. I'm not monstrously big, but it's 8 inches with girth so it's not small either. I want to know the best way to do it with minimal pain, and would appreciate any advice.

I'm also wondering, what to do once I do "get in". Should I only go maybe half way in, or should I just go all the way in so she gets used to it? Will she be able to orgasm the first time?

I also just want to have an idea of what to expect, I've had a lot of sex, but never with a virgin.

Use lots of lube and go slow and gentle, how much/far you go should be judged by her..let her lead the way on that front.

She won't orgasm the first time. Trust me.

Unless you give her one before you insert, that is, which I suggest since it will loosen up the muscles in there.

Still, it will hurt if the hymen is still partially intact.

Dude, Vash and Qwert are right. It is always good to do the "prep-work", before you get down to serious penetration. I've had a few virgins (surprisingly) and except for the first one, when I was just as inexperienced as she was, I have always used lots of lube, fingered (massaged)her vagina, and generally kissed and felt my way to the full monty. The experience will be far better for you both, if she is turned on (mentally)and relaxed (physically).

totally agree with everyone.. the first time is always going to hurt so try to do it slow and be gentle.