Wanting to Cum
No matter what my boyfriend of a year does, I can't orgasm. What he does feels incredible, but it's never made me peak. He can do the exact same thing I do to myself while masturbating, and still nothing. When I masturbate, I can have an orgasm in no time at all. Any idea what might be wrong and how we can fix it?
What a frustrating situation! It sounds like you have a very attentive lover who doesn't get uptight about masturbation, and really wants to hear the details about how your body works. He's doing all the right things, but he isn't getting his just reward. And you must be ready to claw holes in the sheets.
I wish I had a more complete sexual history for you. But here's one quick tip. If previous lovers have been able to get you off, you might take a look at what made that dynamic work and see if there's anything helpful you could transfer to your new relationship.
The clitoris is a finicky little diva, isn't she? It's so hard for another person's hand to duplicate exactly what you do for yourself. A slightly different amount of pressure, bigger fingers, a moment of timing that's off—and you are left panting hard, far from the top of the mountain. But never fear, I have all kinds of ideas that might get you and your man over the top of mountains on the moon.
Change your masturbation pattern. Mix it up. Get yourself used to a variety of different kinds of touches. You can still fall back on the reliable pattern in order to come. But the point is to associate different sensations with that orgasmic reward. Use some lube directly on your clitoris so you get used to slippery sensations. Do it dry as well, if that isn't uncomfortable. Tug on your labia. Squeeze the mons veneris or mound of tissue above your genitals. Put pressure on the top and bottom of your clit. Move it in circles. We want to break you out of this "one size fits all" route to satisfaction.
Next, talk to your partner about masburbating to orgasm while he is with you. Often, the fact that you have another person present is enough to make a girl's private parts get kinda shy. I have heard women express anxiety about what they look like when they come. I say "gorgeous," they say, "crazy and ugly." I'm the one who is right, of course, but until she believes me, she is not going to lose control on my loveseat. Let him hold you or stimulate your breasts, kiss you, bite your neck, do whatever else you like while you masturbate. Once you are able to have an orgasm while he is with you, you have moved closer to your goal. It will take some pressure off of him to know that he can get you furiously worked up, you'll do your thing, and the orgasm you then have will be super fantastic because of all of his great buildup. You might feel less performance anxiety if he would masturbate along with you.
There's no rule that says only one person at a time can try for an orgasm. Instead of insisting on manual stimulation, see if you can strike a few sparks by masturbating while you go down on him. Tease yourself by alternating five minutes of masturbation with five minutes of oral sex. Get your hand on your clit while the two of you are fucking. Once again, we are working at conditioning your genitals to respond to more than one kind of stimulation. If you make yourself come in between bouts of oral sex, that tells your clit that you love oral sex. It makes it more likely that one day you will surprise yourself and come with his tongue on your love-bud. Same thing is true for penetration or doing dirty things for your partner. Diversify!
As long as you know you can come during sex, whenever you want or need to, by reaching for your own clitoris, it won't matter so much exactly who or what is getting you off. You can relax and enjoy everything that is happening, and that orgasm is going to sneak up on you one day underneath his fingers or his mustache.
Finally, another trick that sometimes works is to have sex in the dark. This adds an extra bit of dirty fun and may loosen inhibitions. If the issue is your fear of letting go or being seen as too sexy or too needy, I think he might help you by holding you down or tying you up. That way, whatever happens isn't your fault, is it? Don't do this, of course, if you find it offensive or a big turn-off. But it has worked for some women.