First of all, if you've had sex at least eight times and it's still quite painful/uncomfortable you almost certainly have a medical problem. Though not being able to orgasm is most likely not a medical thing.

Perhaps the combination of the knowledge of the pain that is to come and knowing you're not being treated like you'd like prevents you from having an orgasm.

My suggestions: See a doctor about the pain/discomfort and find someone who you're open enough with to say "Listen here. I give it my all. I expect the same." If they're not willing to try and help you climax then you're definitely wasting your valuable time/abilities helping them reach theirs!

P.S. Almost every male I know would LOVE to be a womans first orgasm. If you tell them no other man has been able to leave you satisfied than they will be more likely to put some serious effort into your time together!

BUY A VIBRATOR.  Something like 80% of women who can't have orgasms have one with the use of a vibrator.

And no, you're not defective.  People come in all shapes and sizes, especially when it comes to sex.  Er, no pun intended (honest).

So far as why sex is unpleasant, it could be that the men you've been with have not been sexually mature or don't know what they're doing (most younger men especially don't have a clue).  There are also medical reasons, so ask a gynecologist at some point.

Also even with foreplay you may not produce enough natural lubrication, so store-bought lubrication will definitely help in the "painful" sex department.

Beyond that, the next boyfriend you have TELL HIM THIS STUFF.  If you're not having fun, tell him.  Giving a woman her first orgasm is a delightful hobby for us fellas : D  You can both learn together.

Since I lost my v-card when I was 20 1/2 ( I had very strict morals), I've had sex with countless guys probably 30 or something like that. I've lost count, after 25 I just stopped counting. (I am now 24). It is very RARE for me to actually enjoy it. I usually have to pretend or just let the guy do his thing and lie saying that it was good (if asked). The only one person where it actually felt like anything..where I could actually enjoy it is...ironically my recent ex. And I was the only woman he ever really got super turned on by (personality and looks). Why did he dump me-he's a psychopath. But I too have wondered if there's something wrong with me, because I can never seem to enjoy sex/love making/the 'f' word...whatever you want to call it. So don't worry, you're not alone. It definitely sucks not being able to really get into it. But I'm sure someday you'll find that guy, that while just a guy on all other accounts there will be some sort of "it" factor where you'll find yourself breathless and mind boggled from the sex. Don't loose hope.

@Goldfinch323@xanga - The other comments I've left may be of interest to you as well.

@Goldfinch323@xanga - Read your comment.

Wondering if you ever considered the fact that you might be a nympho.

[Look up the ACTUAL definition instead of thinking 'addicted to sex'.]

I love having sex. A lot. But it never really feels good, I never 'get off' and I certainly don't feel anything emotionally (even with my boyfriend of almost two years).

@agnophilo@xanga - Oh trust me I def. know what I like and dont like. I also do own a vibrator. 

ouch. I didn't enjoy sex with my first boyfriend because I was inexperienced.

honestly, the only way I figured out how to make it feel good or have an orgams with my second boyfriend was through masturbation. it was really awkward at first because there's a lot you can do, and you don't know what combination of things will feel good or make you have an orgasm. honestly it took me two weeks of trying different things to figure out what was right for me because everyone is different.

the only advice I can give you is that most women cannot orgasm unless they have clitoral stimulation- and that one small piece of advice has helped a lot of friends of mine. (I can't get off without it.)

you need to discuss what's going to get you off with whoever you're having sex with... which is why I don't see the point in one night stands (I'm not judging I swear!) because those people won't know how to please you.

also, if clitoral stimulation does work for you, it might seem kind of awkward to do it yourself if the guy isn't doing it for you (I'm the only one who can get it right in my relationship anyway. he tends to be too rough)... but I mean if you want to get off, you need to get past that. I told my boyfriend it needed to be done and now it's just kind of typical... I do it, it's not weird for either of us, I get off, we're both happy.

anyway. hope I helped somewhat?

also, I only just read the other comments. (my bad.)

when you say you tense up during sex- I know how you feel, I think.
you're concerned about every little thing going correctly.

but, honestly... you let him do his thing, you do your thing. focus on how everything feels, not what's going on. if something feels good, you tell him "just like that," if something doesn't feel good you say "slower" "faster" "not so rough" "a little harder" etc.

honestly the feedback helps them a lot... and it will help you a lot too.

as for pain, it really might be psychological. my last boyfriend, always painful... I'm not sure if it was because he was too rough, or I wasn't wet enough. this boyfriend, I'm a lot closer to and I trust a lot more... no wetness issues, and no pain. it's weird.

some women actually have a medical issue with not being wet enough,  I believe. you should ask a OBGYN about the pain because sometimes it is medical. and if it ends up not being medical... back to square one, I suppose.

as for a lack of foreplay- it is not normal, and it's probably why your sex is so painful. you need to be... pretty wet to enjoy yourself.

@agnophilo@xanga - mhmm and yeah I appreciate the ideas :) I think i just need some reassurance that its not just me. lol

Must be with the wrong people. There are a lot of guys who don't like the whole foreplay thing, but if they care about you they will make sure you get off too. It doesn't matter how long it takes me my boyfriend will work for me to get off.

A lot of women cannot get off from just penetration. They need clitoris stimulation! So get your guy to lightly touch you there. Tongues work well too.

If he cares about you, he will work for you. You have to communicate about it! He needs to hear what you want. Before he penetrates you need to be relaxed, and wet. It might be too much info, but it's true.

if you are anxious, stressed or not that turned on, there isn't enough natural lube, so it hurts. try the artificial lube. maybe he isn't fast enough. that is usually the problem for me. it has to be fast for me to orgasm. vibrators are so easy to reach multiple orgasms that I sometimes wonder why do I even bother with men hahahah I just prefer to cuddle more than sex. for some guys, it is the opposite.

If you've never given yourself an orgasm, it's probably unlikely that someone else is giong to give you one first. You should get to know your body. Learn what feels best for you. Try out different positions and experiement. Faster, slower, deeper, to the left, right, up, down. If it's painful, it might be because you need some lube [and no, i'm not trying to be funny.]

Make sure you're comfortable with the person you're sleeping with. If you're not 100% into it, ready and really wanting it, you're not going to climax.