Hey everyone! Let's get straight to business, shall we?

I masturbate. I've done so since gradeschool, more during middle school and petering out around the end of highschool. I've always done it the same way- stimulating my clit by rubbing on towels and pillows and such. I've almost always reached a lovely orgasm this way. But, also around gradeschool, I vowed to remain a virgin till I married and have kept to it nicely.
I've never been in love with someone that would and could ever love me in return... until now. I met my steady boyfriend future fiance (once our friends and relatives seem okay to handle the news of us being engaged) and we immedietly clicked.

Of course, since I had some energy pent up, I didn't stop him when his hands started travelling south and was quite excited when he began touching me. I got comfortable enough with him to penetrate with his finger and I liked it quite alot, even though it hurt a bit the first few times. Every single time I think I'm close to orgasm and can tell he's getting tired, I keep trying and trying but eventually have to give up and fake it so he doesn't feel bad. But then I feel bad, and quite tired from trying to hard.

I think I've now faked almost a hundred orgasms, and even when I use his pelvis/leg/underwear-covered shaft to stimulate myself.... I still can't reach orgasm. The wird thing is, when I masturbate alone as I always have, I reach it quickly.

What's going ON?!?!

Never, never fake it. It's a really bad pattern to get into and if he knows anything about women he can tell because you can't fake the muscle spasms. Foreplay is about arousal and communication you are bypassing both. If you are aroused being fingered shouldn't hurt -that's pretty tiny compared to what's meant to go in there. Now how are you going to tell him that what he's been doing hasn't really done the job? It may be best to tell him you'd like to try something different and start helping him explore what turns you on. You have a head start because you are an experienced self pleasurerer. You may have to show him what it takes, where and how you touch yourself. Right now you are setting the pattern for years of sexual interaction. If you want it to be good you've got to get the foreplay right. Personally, masterbating takes me quite a while to orgasm but when my lover starts to touch me I have a much faster response and often start to cum immediately. That is based on a response cycle, everytime you have really good sex, it makes you more responsive the next time. You've been training your body and mind against that.This isn't about his ego, it's about shared pleasure, you'll have much happier lives when you quit pretending and start making it real.

It doesn't hurt me anymore, just back when we first started doing it. Now I feel so conscious of him enjoying my facial expressions and sounds that even when I feel like I'm about to come, I don't. Its dang frustrating! He gets me going so quickly, so thoroughly, but I can never orgasm! Not even when we have phone sex. What's going on and how can I fix it?

(Thanks, WildChild. You're right on the whole getting myself into a negative routine... It's just, I've gone so far, and faked so many -I can make myself spasm, by the way, by contracting somewhat- that I'm scared if I tell him he will feel inadequate or something...

My own experience (everyone is different) I can orgasm as a release or in total relaxation. In build up and release, I have to stay focused on my body and the sounds of arousal, my lovers voice, an occasional swat or pinch on the rear or even being told to cum, keep me going and going. Orgasm in relaxation is quiet, less intense but even longer lasting and with that I clear my mind and simply become what I am feeling. You may benefit from some reading on different techniques. Drs Steve and Vera Bodansky teach and have two books out on extended massive orgasm (EMO) that deal with orgasm through relaxation. The Art of Tantric Sex is a good beginning for that, it probably helps if you are experenced in yoga relaxation techniques and/or meditation. There is tons of stuff on other sexual techniques, just experiment and find what works for you. Note that most of the film orgasms you see aren't very real. Studies have found that usually both men and women at orgasm bodies go kind of rigid or stiff, not thrashing around.

The longer you spend in foreplay, the more you try and experiment the better experience you will have later on. Sex is one area where you have to be real and honest. For us women a lot of it is in our heads - although poor sexual technique can prove it isn't ALL in our heads! So mental state is critical and thinking you have to meet some sort of expectation, like passing an orgasm test, won't get you where you want to be. Many women don't orgasm regularly, some of us do almost all the time and some apparently never do. You need to get over the idea that you have to meet some sort of expectation on his part and focus on your own pleasure. Don't worry he'll get there with or without you, men are good at that, too good at it. You are actually training him at that by not letting him learn what really gets you off.

Don't worry about your facial expressions, what he enjoys is thinking he is seeing your pleasure. It will be a lot better when it's real. Get off the stage, you aren't performing for him you are sharing your pleasure with each other. Sometimes it's all about him, like when you are giving him a blow job or hand job, the rest of the time it's about you. When he is in you and you are loving it, he'll be working to hold himself back, his pleasure really won't be much of an issue as long as you are really cumming.

You'll get there. But you have to be honest. There are few things that will mess up a relationship faster than one or both of you being sexually frustrated, you don't want years of that, you have to fix this or move on.

I didn't have an orgasm until I got with my fiance. I don't know if it's cause hes the only person I ever loved or if hes the only one who hit my spot right. I honestly think its a little of both. When the penis is inside of you , your spot (most womens) is on top . So the top of the penis is hitting it. Some spots are father back then others. My fiances penis has a curve in it. So his head is always hitting my spot. maybe your the same way and haven't found someone who hits it right. You might just not be comfortable with yourself so in return you can't feel completly comfortable with others. Why don't you try masturbating to porn on anything and see how that goes. Then use a dildo and only a dildo. Once you've accomplished an orgams from that . Then try intercourse and see what happens!!

You need to tell him you were faking and quit it altogether. It's NEVER a good idea. As WildChild said, you've set a bad precedent by doing that. His ego might be bruised but he needs to know that you're just not fully satisfied. It seems you enjoy the things he does to you, you're just not "going over the edge" so make sure you stress how much you enjoy things and explain the reasons you started faking (wanted to please him, etc) so he knows where you're coming from.

Then just maybe scale things back a bit and start over with your communication skills. Direct his hands with yours. Verbally tell him when something feels good. Work on being perfectly comfortable with him to the point where you're not focusing on your facial expressions or anything else but just letting things happen naturally in response to what you're feeling. If you get caught up in thinking about how your face looks or how bad you think he wants to see you in pleasure, you will be way too distracted to let go enough to orgasm.

the clitoris is the key. have him stroke that. And you'll have an orgasim.