Other helpful discussions on First Time:

If you were going to get someone a toy who had never had one before...
...What would you go with? What if you didn't know what they might like. For couples or by themself. Either way. P:

first time
whats the best toy to use for a beginner?

Your ideal first time threesome? A purely "What If" question!
This is purely a What If question, so please answer it that way. I'm not asking if you would or wouldn't or if you have or haven't, I'm just asking..

Tips for first time strap-on sex?
so im in college and my girlfriend is living back home. we discussed strap on play before but never got around to it. then one day she sent me some...

My first time.
I have never used a vibrator before and I just wanted to know what should I go with first. Are there vibrators for first timers or should I just jump.

Has she gone to an OB-GYN? Generally, it's good to go before the first intercourse to check that everything's okay and to potentially get birth control.

She's a virgin, it's a pretty natural state to be in...

Try using slim toys to get her muscles used to stretching and always make sure that she is well lubricated before trying to have vaginal intercourse. For the first time, it would probably be best if you were on top. If her hymen is still in tact it might take a good bit of thrusting to break through to the other side.

Use fingers to gradually stretch her out.

Perfectly normal and sounds just like me. My first time we actually tried about seven different times to try and get it in, so we just stuck to foreplay while he gradually stretched me a bit. It went over weeks; its pretty painful. Then one day we were finally able to pop in the head, and no joke, it took about thirty minutes to get it all the way in. We decided to slowly inch it in so it didn't hurt me. Trust me, she'll appreciate it if you go slow too!

Make sure you're protected too!

Definitely normal, but seeing a gynecologist is an option (especially is this continues). As the others said, she will gradually need to be stretched. The first time I ever masturbated was even rough. Go heavy on the foreplay to help her relax. She made need some time, but it should all work out!

I agree that it would be a good idea for her to see a gynecologist. She may be experiencing vaginismus, an involuntary clenching of the muscles in the pubic area. However, the exam may not verify this: " Generally, when the attempt to put something in the vagina has ended, the muscles relax and return to normal. For this reason, medical examinations often fail to reveal any apparent problems unless the tightness occurs and is noted during the pelvic exam."

My mother reportedly had the same problem when she got married, as she was a virgin, and I suspect the teachings of her religion were involved with causing her involuntary muscle contractions. In a way, vaginismus is the female version of erectile dysfunction. It's not the woman's fault, and it's not under her control.

I wouldn't suggest just pushing through the resistance, as a painful experience is likely to cause the involuntary clenching to become worse through negative associations. I would suggest avoiding any vaginal penetration at all for awhile, and just focusing on all the other kinds of sexual pleasure you can give each other, such as all-over touching and kissing, manual sex (handjobs, and touching/rubbing the clitoris), oral sex, using external toys together (such as vibrators), and whatever else you can dream up. Be creative, and maybe read some erotica together for ideas. After you've gotten pretty good at making each other feel good in those ways, and she feels really ready after a lot of teasing, try using your finger or a very slim toy (like the Small Silk from Tantus, or a smooth plastic vibrator). If that works, meaning it feels good to her and isn't painful, then do that a few times, and then, next time you have sex, start with the finger or small toy, then move up to a slightly larger toy. Two fingers are usually fairly thick, so you might go from your pinky finger to your index or middle finger, rather than from one finger to two fingers.

Keep increasing the size of the penetrating item every few times you have sex, but starting off with the smallest item and working your way up through the different sizes. With patience and time, you'll hopefully graduate to a size close to your penis' size, and be able to have intercourse.

Try to remember, though, that there are many ways to have sex that don't involve a penis inside a vagina, and you'll be cutting down on your chances of pregnancy this way, too. Don't get frustrated if it takes a long time before she can even handle a small toy--just find other ways to get each other off!