You may want to schedule an appointment with her OB/GYN to rule out any physical problems. It's possible she has a form of vaginismus.

We have both tried to insert it to no avail. She has been able to have toys and a speculum inserted without problem. We think it's either psychological, or the angle perhaps, but then again, we're not really experts, which is why we're asking asking. When I insert, I don't feel anything and if i thrust, she either feels nothing or pain, while I don't feel a darn thing. The more we try and fail the more I'm amazed that teenagers are able to figure this out. Is it supposed to be this complex?

Have you tried letting her warm-up with a toy first?

Are you able to insert your fingers?

Are the lights on?

All of these things can be helpful. Using a toy can help loosen her muscles and might help alleviate some of her psychological stress. Your fingers can do the same, and you can use then use them to help guide you in.

lights on, haven't tried used a toy as foreplay, but she tested herself with one after an attempt to see if it would insert and it did. I am able to insert a finger, but the index finger is usually too large.

I should have asked earlier… what toy? Large? (like a dildo) Small? (like an egg) Hard (like plastic)? Soft (like silicone)?

Right now my guess is that it's a combination of nervousness and insufficient arousal. If she's able to insert a toy on her own when aroused, you should be able to insert an index finger. I actually would not try for anything larger until she can comfortably accommodate two fingers.

it was a plastic dildo less than one inch in diameter (i can't recall the name, or I would have included a link). I tried arousal, plenty of foreplay, then lubing myself and putting some water-based lube in and on her, but still, nothing. we've tried this about 4 or 5 times already. Pretty soon we'll have to get a new box of condoms.

I'm going to agree with Yaoi Pervert, it sounds like she's tensing up. A dildo less than an 1" in diameter is on the small side, but clearly she's able to insert something larger than your index finger.

As Yaoi suggested, a pillow might help, and if you haven't already, let her try putting your penis in her vagina. She should be able to feel when you're in the right position.

Another option is putting off PIV sex for a little while. If you've tried nearly a half dozen times with no success, it can only be adding to the stress. Have some fun just using hands and mouths with one another. Or ask her if you can use the toy on her (it sounds as though only she's used it on herself). It will help you both become more familiar with each other's bodies, and more importantly, relax you so you feel less nervous the next time you attempt PIV.

Good luck!

I fully agree with Petite Valentine, the boyfriend and I were having the same problem. We were 17 (he 18) and we thought we just didn't know what we were doing.. Years later (still with the same guy) I finally went to the doctor and found out I have vaginismus. It's 100% treatable. I would highly recommend seeing OB/GYN.

I've tried pillows, but they may not be large enough. I have an inflatable wedge that I've been meaning to try. As for the condoms, the listed expiration date is in 2013. Unless those dates are often off by a year, it should be okay. I haven't tried that link you gave, but am doing so now, thank you.