I'm going to go out on a limb and say that if in 5 attempts, you didn't make it, and it isn't a size problem, that she should see a doctor and explain the problem, and maybe he/she can alleviate the problem by using an instrument better suited for opening a really tough hymen. I would say it is no big deal for the doctor and then you guys can get busy.

"I mean if it's only for a sec than I don't know why it is such a big deal for her..."
It may not be only for a sec. I had really bad pain my first time and for a few days afterward. And why shouldn't it be a big deal? It's her virginity for God's sake!

"I have to tell that she's a prissy girl and sometimes she's a bit whiny for my taste"
Why do you have to tell that? I think maybe you suspect that the reasoning behind her pain is that she doesn't really want to do it...And if you're still pushing her, you're a cad.

"but I mean that's the girl I wanna be with definitely if there wasn't this bit of a problem between us!"
"If" there wasn't such a problem? You should want to be with her whether or not there is a problem like this if you expect her to give up her virginity to you.

I hope it's just your choice of wording that's sounding suspicious, and you're not just out to get her to give it up and then dump her.

I have to tell you... the first 4 or so times that I had intercourse with my boyfriend it HURT! The whole time I was just thinking "Well, I have to get this over with some time." I would seriously bite my tongue to keep from yelling out in pain. I couldn't wait for him to cum and have it all be over. It REALLY sucked for me... every woman is different... none of my girlfriends had this experience. In fact most of them said they felt no pain. For some reason I was different. Now I LOVE sex... I just had to go through that excruciating pain at the beginning... and it WAS excruciating. I guess I was just REALLY tight. Tell her to use a dildo to stretch herself out.

Wow, you really are blessed! I had horrible pain my first time, and for days afterward. We really are all different, I guess.

once a year at least
so maybe its due for check up time.
then you could go with her and you both could talk to the gyn about it.
the support would show that you care and you yourself can get re-educated on sexual health.

http://my.webmd.com/content/article/64/72263.htm

Love Hurts

How does a couple proceed when the act of penetration is just too painful to allow for intercourse?

By Louanne Cole Weston, PhD
WebMD Answers to Questions

Question:

"My husband and I have been married for almost three months now, and all we do is hug and kiss and cuddle. I admit it is very nice. but I feel like we're missing out on sex real bad. Initially in the marriage he had gotten turned on, but we were not able to have sex. I'm a virgin who's obviously got a tough hymen or something. It's like he tries to push in and it somehow slides out, no matter how hard he is! He says, 'It's like you're pushing me out.' I am kind of apprehensive about it, and the times part of his penis has sort of gone in, it was very painful and I had a burning sensation for the next half a day. If I grimace or he feels that I'm in pain, it turns him off. He wants it to be a pleasurable experience for both of us, and I'm really lucky that I've found a great guy, but he just doesn't seem to be aroused by me any more.

"I asked him if I should try and reach in and break the hymen somehow myself so that it won't hurt so much and will make sex more possible; of course, he got mad at that suggestion and said that he wanted to do it the right way. He just wanted me to relax a little more, etc. I try to relax, but I don't know what the problem is. He doesn't want to see a doctor for me yet. He says first we have to relax and keep trying, but I can't even remember the last time we tried. I truly love him but have no idea how to make this happen. Any suggestions?

P.S.: He also thinks that I've been reading too much on vaginismus and stuff like that since before we got married, and that's the reason why I cannot psychologically accept him getting in."

Answer:

As great a guy as your new husband may be, he is misguided on a few issues here. It sounds like he is strongly attached to the idea that he is supposed to "break your hymen" (doing it the "right way").

Your reading about vaginismus is not a problem, it's a help to the situation. I have never encountered a woman (or even heard of one) getting vaginismus from reading about it.

You may very well have vaginismus (defined as a clamping down of the muscles at the opening of the vagina) when intercourse is attempted. (Some women also get it when they attempt to insert a tampon or have a gynecology exam.) It sounds like you have that happening because it feels to your husband that you are pushing him out.

You also seem to be having dyspareunia (painful intercourse).

If you haven't already read Private Pain by Ditza Katz and Ross Lynn Tabisel, do so. Meanwhile, you absolutely should see a gynecologist -- preferably one who is an expert on pelvic pain, vaginismus, and dyspareunia (not all are well versed in this area). This is not something that romance and fortitude are likely to solve. You may have good intentions in enduring this painful intercourse, but it's not likely to help your sex life have a good start. In fact, it could make you both avoid of sex (which it sounds like is already happening).

In order to keep your sex life on a steady, healthy path, I'd recommend a visit to the doctor, additional reading, and self-exploration on your part if you wish. There are plenty of soft, pliable inserters available from companies such as The Xandria Collection and Good Vibrations, which you could try. Be sure to use a lubricant or be very wet from your own lubrication before using an inserter or trying again with your husband.