Her First time...Every Time

This was way too long pre-editing. Let me try again.

Basically, I have been seeing a girl for almost 4 years, and we started being intimate after the first year. We were both virgins when we started dating, and even though we thought we'd hold off on sex, after a couple years of thoroughly enjoying "everything but," we decided to have sex. It was far more difficult than either of us had anticipated. I always found that using 2 fingers prior to that time caused her pain, and I just assumed this was because she was a virgin. However, after trying to have sex numerous times, I'm not sure what the problem is. I've never been able to fully penetrate her, and it took me months of repeated tries before I could even get in more than a couple inches. It seemed every new millimeter I entered her caused her excruciating pain, and I cannot be aroused when she's in such pain, so naturally, I go limp. We hardly even try sex anymore because it ruins the intimacy to have these repeated failed attempts. When we do try, I am now able to enter 3/4ths of the way, but that is the deepest I can go, and she's still in immense pain, so obviously I never get close to orgasm before going limp. I'm quite adept at giving her orgasms through other means, and I have tried penetrating right before an orgasm, and right after so there's more than adequate lubrication, (i also use store lube in addition.) We've tried numerous positions, from ones giving me all the control of entering, to ones giving her all the control, and ones that combine, but every time, if I even get to the point where i'm maybe 5 or so inches in, and can adequately thrust, the action dies down when I see she is not only Not enjoying it, but pretty much looks like she's hating it. It's gotten so bad that even though (Admirably) she still suggests we keep trying, despite how aroused I am prior, sometimes at the mere mention of sex, I get so uncomfortable at the idea of a repeat performance (which is not only embarrassing for me, but means that I will not get to have an orgasm at all that night) I go limp before even putting it in. I'm developing a phobia of her vagina. Has anybody had similar experiences? Is there anything else I can do? I try to make her as comfortable as possible, and be as romantic as possible, but nothing has worked in the past and it's extremely frustrating! Thanks in advance.

Hey Indus,

I feel for you man. I did actually have a similar experience with my 1st proper girlfriend. (Which upset me).

She even went to the doctor about it asking if perhaps my penis was too big for her (gee that sounds a bit vain, I don't mean it like that, I'm just mentioning she said that to explain what happened)...
The doctor apparently told her "a vagina is built to be able to have a baby come out of it... no a penis is not too big"

But when you can feel yourself hitting... and she's in pain... you do wonder.

I have heard that a lot of guys with large dicks sleep with guys because of this.. 'cos obviously inside a guy there's no er.. stopping point.


It could just be the virgin thing though... but seeing as you said you've pushed in about 5 inches... I'm sure u broke the.. thingy... hymen.

Hmmm. I really would suggest that she goes to the dr and gets everything checked out (not meaning to panic you, she's probably fine, but it's best to make sure everything's ok right?)

It might just be a case of you're too large and she's too petite... maybe you'll just have to not push so far in dude.
Most of the sensitive nice feely bits for her are more around the actuall opening of her ladyparts anyway.
I know it's a pain because you want to push all the way in though.

But I learned not to always do that when my ex girlfriend literally ripped chunks of flesh out of my back with her nails and I was like "OW.. was that in passion??"
And she said (looking really angry) "no.. because you hurt me!"
So I totally understand what you mean about her looking like she hates it thing.

I would have said it was the anxiety, tying you both in knots and stopping her being able to relax enough to let you in ... but seeing as you use loads of lube, perhaps this isn't the case.

I guess maybe try both being really really relaxed and horny and using loads and loads of lube.
Maybe she needs to practice penetration with a sex toy on her own (or even with your help if she wants) and get her used to recieving things and being relaxed enough to be able to.

Hope you get it sorted out soon.

Don't do anything to try penetrating her now. Some women have thick membrane or other deviated structure. Though in a very low rate those do exist. Find a good doctor to check up first. If nothing wrong with physical structure, then you can consider to useing love skill.

I'd like to thank Fahrenheit for his long and thoughtful response. I've suggested the toy thing because I really think practicing on her own might be the solution, but, maybe as a result of her growing up in a conservative Indian household, she seems very opposed to it.

The other day, however, when she was a bit...overgrown...I suggested she use the hair-trimmer that I use for my own personal grooming (not my head hair, lol), and the vibrating of the device was so new and exciting to her, she ended up giving herself an orgasm from it. She told me she would be extremely offended if I bought her a dildo or anything like that, yet from that alone I saw her fondness of toys in general.

Any ideas as to how to pursue this further? If not, any ideas other than toys?

P.S. I appreciate that the story makes it sound like my penis is monstrous, but truthfully, from what i gather, though it's definitely on the long-side, it's average thickness at best, which is why I can accept that maybe it will not go all the way in until sex starts going smoothly and she stretches a bit, but as for the width, I really didn't think it would be a problem for her.

P.P.S. She had a gynecologist's visit recently and mentioned the problem, but (i obviously was not in the room, and I don't know if she was entirely truthful) apparently the doctor said everything seems normal, and that she didn't think she suffered from anything of concern accept htat maybe she was nervous, or her body had conditioned her to tighten up because of the initial pain of the first few attempts.