Dear Amy,
Be patient with what is happening. My gut feeling is that you are fine. If you are seriously worried there might be some sort of anatomical problem, get a checkup with a doctor.

Your boyfriend is fine and this is not unfair to him. It is who you are and I suspect he is happy to have you. You are a couple and if he's a good boyfriend, he cares about your comfort and happiness. Try not to worry about this quite so much and enjoy the lovemaking for what it is. I suspect you two will figure this out before long. He will not be harmed by not being inside you a few days or weeks sooner.

I really don't think it's an anatomy problem because it looks perfectly normal from my opinion. Even my mom said she had no problem losing her virginity quickly. I really don't know what the problem is. I hope we figure it out soon.
Thank You A lot!

OK, I'll ask a question. Before the insertion attempt, both of you have engaged in foreplay and you should be well lubercated?

You have to practice finding your vagina with your finger in this state of arousal.

His condom needs to be lubercated as well. Now you can gently show him the way.

It may take repeated trials for his penis to gently enlarge the opening. If you can guide and aim, it will be a big help.

You don't want him to find the opening and for him to push hard.

Do it gently at first, and you'll know when you'll want more.

Alternatively, since it's your first time you can be on top and be totally in control in what's known as the cowgirl position.

I agree with Keep it Simple. Slow and gentle. But it could be difficult for Amy to guide him if she's now in doubt about where he should go. Also, breaking the hymen is sometimes pretty difficult, even under the best of circumstances. Thinking about it, I realize I had almost the same problem, a few decades ago. It had kind of receded in importance.

Well, I used to think that cats peed out of the end of their tails. In case you're wondering, they don't.

You really don't need to be afraid of your own body. In fact, you're going to have to be your body's representative for the rest of your life, so it's important that you know what everything is, where everything is, and how everything works.

It appears that somehow you got the impression that looking at your own parts is a bad thing. Let me promise you that everyone does it. We have to for a lot of reasons.

Your mom does it. Your grandma does it. Your teachers do it. mrs. santa claus does it. Even the Queen of England does it. Everybody does it.

So go pick up a hand mirror and make it your new best friend.

Don't look! Just kidding. You're supposed to look. It might not look like you thought it would be. It appears you've had help through diagrams. I know I had seen diagrams of the male anatomy before I got a glance of the real deal, but I still had the idea that it would look like a long balloon with a nipple at the end of it. It doesn't look like that, by the way.

So just get used to the idea that this is part of you. It's not stuck on. You're not like Mr. Potato. It's part of what makes you who you are. Wave. Beyond the health aspects that make this an important step, you'll also find that you need to be intimately familiar with this happy place if you're going to enjoy sex and all of its intricate blessings.

In answer to your other question, the anus is completely independent. All it does is poo. It's the little hole in your butt. It's where the term "a-hole" comes from. Say hi to it. He's your friend too.

I agree with the advice given to see a gynecologist. I was always told you should go when you become sexually active or 18.

Since you have considered vaginismus might be an issue, I would recommend it even more. I know you wrote that it doesn't look like an anatomical problem because everything looks normal, but I don't know if vaginismus is entirely visible or if it's occurs to the same degree when you're by yourself.

You can also tell your doctor your other concerns and questions. I can assure you that they've heard it all before, and they won't be offended. They've dedicated their entire professional lives to this one little part and all of its anatomical friends. Do not fear. The Lord made that too.

Amy,

Your boyfriend has to push HARD when lightly stroking your genitals with his penis from the front of your genitals-your clitoris, urethra and boom into the vagina; his penis will go into your lubricated vagina. It may have to break your hymen if it is intact and that is painful the first time. The missionary position will give him a good position so he can push hard. Your anus will be out of the way in this position.

Thanks Everyone for your helpful answers... especially the very long one!
Yes, we do foreplay and no, we haven't used lube or anything like that. We also don't have lubricated condoms, so basically its been relying on my own wetness, etc... which I started thinking could be a factor by itself. I got lube today. We also tried to have sex again today and he fingered me beforehand and only one finger fit inside, and if two even attempt to fit it starts to definitely hurt. It confuses me how one finger can fit inside, yet a penis isn't fitting. I'm also starting to question if my hymen is still completely intact or not because of the fact a finger does fit... because I know you can partially lose your hymen as a kid. We have tried almost every position and it's still the same thing. Today the head of his penis fit in, but no more than that. Really confusing. We're going to try and use the lubrication the next time we try again. I really hope it works.
My question might be going on and on for something that seems like a simple problem, but all of your answers have been really helpful and interesting to me because this is something that's been frustrating me for quite awhile. We've been together for over 6 years lets just say (including high school). So I am QUITE ready if you catch my drift!
About vaginismus, I hope & pray I wouldn't have that. I mean judging from myself, I don't see why I would have it because I really am not like terrified of sex and nothing in my childhood happened to me that would cause me to have vaginismus. I started questioning stuff like this because of how hard its been to lose my virginity. Especially because from hearing my friends talk in the past about them losing their virginity, they said it was pretty damn easy... literally, like two times of having sex and it was all good.
I'd like to hope that this happens to a lot of girls when trying to lose their virginity and not just me! Thank You for all of your answers!

Just take your time. There is no need to rush. Tell your boyfriend the issue your having and if he really loves you he will understand. Just keep trying to have sex and go farther in each time and eventually you will be having full sex.

First, I don't agree. Sometimes medical intervention is required if intercourse is always painful.

Second - this is from 2008. The OP is long off the Board.