Cannot penetrate girlfriend.

She's a virgin, and I simply cannot enter her vagina. We've tried multiple times with extensive foreplay and plenty of lube. My penis simply does not enter her. Not even the entire head. I can only fit one finger inside of her, and if I try two of them, she screams like a banshee and bleeds all over the place. She is always soaking wet and I usually perform oral on her and she has multiple orgasms, but we can never have intercourse.

I told her that she may have to lose her virginity to someone with a much, much smaller penis. But she insists that she wants to lose it to me.

I don't understand all of the contradictory advice I've read either. I've been told that I have to be super gentle and I've been told I have to force myself in. Considering how much she bleeds and how painful it is for her already, I don't think forcing it in would be the best solution. I don't understand how it can be this painful. Everywhere I look online says that it hurts "a little bit." Yet she tells me it is the most painful thing she has ever felt. She cries and looks at me like I'm a monster with a penis made of razor blades. It's ridiculous and if she didn't insist on having sex with me I wouldn't even bother. I have no desire to torture someone with my penis. I want to have enjoyable sex that is fun for both parties with a lot of smiling and happiness and pleasure.

And lastly, no I am not trying to penetrate her urethra. I have slept with many other women and I understand how it works. This is the first virgin I've dated.

Thanks and I apologize for my blunt attitude but this is frustrating for both of us.

[Anonymouse88]

Well, it seems like you've tried the first line of advice, which is using lots of lube and going slowly.  If you can't fit two fingers without her bleeding, though, you won't be able to fit a penis right now, and you shouldn't try if it's making her bleed.  Definitely don't try to force it.  She should maybe see a gynecologist to make sure there's nothing medically wrong, since it causes so much pain.  In the mean time, the best thing is probably to work up to it with variable sized toys.  An anal training set might actually be a good place to start, because they have various sizes of tapered toys that start at a very small size.  You can work on them together while she's really aroused, since that makes penetration easier.  She should also try to masturbate with them, using plenty of lube, so that she can gently and gradually stretch herself out.  They also make inflatable toys, which can be inserted and then inflated just enough to stretch a bit.  When she's worked up to it, and you're ready to try intercourse again, let her be on top and control the pace.

Good luck, and have fun!

[AnnieBrooke]

In her shoes, I would see a gynecologist.  Some women do have a much thicker hymen than average, that might be what she has.