Maybe not enough lubrication? Also maybe it's just that you're really tight?

Also is he circumsized? I was friends with an intact guy and he said that the first few times he had sex it did kind of hurt because the foreskin wasn't as used to moving in that way or something.

Yeah the circumcision thing is a big one. My dad had this problem when he first go together with my mom. What happens is if they never have pulled the skin back before it is tight and when it gets pulled back during sex it can hurt. It will go away in time though so don't worry . The best way to get it to go away is have more sex and stretch that skin out.

I really can't see how you bodies would not be compatible. As far as the bending I'm rather perplexed because I haven't herd of it before. Is it bending? I guess that's the real question. Maybe you have a curved vagina?

By not being compatible I meant that my vagina seems to be shorter than his penis, and that he seems to be very sensitive and need more gentle, shallow thrusting and I am not very sensitive and want it hard and deep.

I have no idea if it's actually bending. All I can go by is what he says, and he doesn't seem to really know what's happening either. I thought the painful bending sensation was caused by him hitting my cervix, but now I'm wondering if it's from his foreskin being tugged too hard. Or maybe a combination of the two?

Well it's a good time to establish some communication. If you don't mind me asking how long have you been together? He probably doesn't want to talk about it because he is feeling insecure about himself sexual. He probably doesn't understand why it's hurting either and is upset because he think that something could be wrong with him. So it is a sensitive topic, but in order to figure out what going on you both are going to need to have an open line of communication. You need to have sex again and this time you need him to tell you exactly how and where it hurts, and what he is doing when it hurts. That way you can figure out what is happening better. As far as him taking a long time to cum, don't rush him, it's better that he take his time then rush. It's also better because girls take a little longer to orgasm then guys so just enjoy yourself.

We're not actually together. We started as friends, then became more for a while, but we're back to being friends, except now we're having sex too.

And yes, he is insecure. We were both virgins but I have had experience with other guys, and he has never dated or even kissed another girl. I tried to made a joke about how maybe we're just doing it wrong because we're inexperienced and it hurt his feelings.

I think we might actually take a break from sex for a while. It's causing too much tension between us right now, and he's not really enjoying it, which makes it hard for me to enjoy it, so what's the point?

But if we do decide to try again, I will ask him to tell me as soon as he gets the feeling, rather than waiting til later to try and figure out what happened. Hopefully that will help.

This is a dumb question, but do you mean that he should be seeing a doctor or that I should?

It's the best to start as friends, but I'm am confused because if you are having sex but say you are just friends, is there an emotional attachment going on, or are you just doing it for fun? I think you need to establish what sort of relationship you got going on before you take another step forward. If you are just friends and don't have any deep feelings for each other then leave it at friends, but if you are attached to each other then you should start keep going forward with the relationship. And here's another thing you don't have to be formally asked out to be boyfriend and girlfriend it just kinda happens. Me and my man were best friends and then started doing stuff and became boyfriend and girlfriend even though we never really established it.

As far as taking a break from sex, it will not make him hurt less and may end you newfound sex life on a bad note. On the other hand if you don't really like him end it, because you don't want to lead him on. I say that if you really like each other keep having sex because the only way you are going to get a better idea of what is going on with him is by communicating with him and asking him what hurts and where. Also you can stop having sex but still play around, I recommend taking a step back from sex and start experimenting with oral and try mutual masturbation. It will take his mind off of sex and you two can get a better idea of what you like and how you like to be touched. You will also learn more about each other which will make sex a lot better.

As far as him being insecure you need to be extra supportive in your sex life. If he is good tell him and reassure him that you want him. He is facing a really critical point in his life and probably feels defective sexual, that's a big deal! He's faced thoughts that he will be in pain every time he has sex that is scary! I would feel really depressed if I were him. So you have to understand what he is going through and be sensitive about it. Hope this helps some.

How would you describe your relationship? Like what do you consider it?

Also try not to get to down when he says that you could get better then him. Just reassure him, that could also be taken as he thinks he is really lucky that you choose him. Also respect his feelings and don't pressure him to talk, guys always react badly when they are pressured into doing something they are not ready to do. If he does talk about it don't over react and make sure to listen don't give him all sorts of advice like we girls like to do, just listen to what he's saying and after he's completely done talking about it then you can talk. He will talk about it eventually but he just is not ready to yet. It's very important that when he does though you react good otherwise he may worry about telling you things in the future because he is scared of how you will react.

I consider it a friendship, like I said I don't want to pressure him to talk about it, but at the same time I find it ridiculous that he waits to tell me til after that it hurts, and only if I ask whether it did. Why suffer through it when he could tell me and we could stop and try something else?

He's trying to please you and doesn't want to make you feel weird during sex. He is putting trying to please you ahead of his feelings. Also does he view it as just a friendship? And if it is just a friendship then would you be open to dating someone else at anytime because you don't consider it anything more than a friendship?

I've heard lots of girls talk about sex being painful for them at first, and the guy having to take it easy, but I've never heard anyone talk about it being the other way around. Glad to know that it's happened to other people and that it worked out okay for you in the end.

I figured as long as I was wet that meant I was ready, but after your last post I did a little reading. I never knew that the vagina actually gets larger and the cervix moves back when a woman is very aroused. So maybe I haven't been waiting to reach that stage before we start...

Most woman hurt when there cervix gets pushed up against though so I don't know if he is actually hitting you cervix and even if it is I don't understand why the would make him hurt.