The Pro
From Candida Royalle:
First, allow me to dispel the outdated myth that women “should” be able to cum through intercourse alone. You may not need to hear this, but clearly you are allowing yourself to be inhibited by the fact that so many still do, and believe me, you’re not alone. Countless women—and men!—still buy in to this assumption, which has been perpetuated since Freud declared that the true “mature” orgasm for women is that which is achieved through intercourse, the “vaginal orgasm.” This is simply not true. In fact, Shire Hite made big waves back in the ’70s when she published her famous study, The Hite Report, which stated that as many as 85% of women do not have orgasms through intercourse alone. And it’s not due to some psychological problem or something that can be overcome. Because of the placement of the clitoris, it is often difficult if not impossible for the penis to directly stimulate it through intercourse, and clitoral stimulation is required for a woman to climax.
Next, it’s time to stop faking and to stop worrying about all this stuff when you should be enjoying yourself. Fact is, the minute we gals start worrying about coming while making love, it’s all over. Reaching orgasm requires that we be able to let go physically and mentally. So lay back, breathe deeply so the blood can get “down there” (which is needed for orgasm_, and start thinking sexy thoughts!
You have two choices: Either you make up your mind that you’re simply going to reach down and do yourself while he’s doing you, or you come clean and tell him what’s up. If you do decide to just be honest, start with the positive and tell him how much you’ve loved the sex. Then explain to him that you’ve been embarrassed to admit that you require direct stimulation—which MOST WOMEN DO!—and that you’ve been too shy to let him know and didn’t want him to think less of you or feel like he wasn’t enough. He may be a bit miffed at first, so allow for that. But if he’s any kind of man, he’ll get over it and be happy to accommodate you.
As for bringing up the idea of masturbating, again, make it a “positive.” Say something like, “It would really excite me to be able to stroke myself while you’re inside me...” or whatever it is you like. Maybe you can even teach him how to do it himself if you think you’d like that.
If you want to introduce a toy, be sure to make it sound like it’s sex-play for both of you. Include him somehow so he doesn’t feel like he’s left out or unneeded. You can say, “It would turn me on so much if you would put your (fill in the blank: his cock, his fingers?) inside me while I use this vibe on myself.” Or maybe you could show him how to use it on you. The point is to make him feel like he’s part of the fun. No one likes to think they’re being replaced. Let him know that it’s the fact that he’s there with you that’s the turn-on.
And here’s one other little piece of information that should inspire you: The most powerful and delicious orgasm for a woman is when both her clitoris and the small area referred to as the G-spot are stimulated at the same time. Let him find and stimulate your G-spot with his fingers or a G-spotter while you stimulate your clitoris. Once he sees the pleasure that brings you, he should be thrilled to have learned this little trick that brings phenomenal results!
Bottom line: You need to be honest about what you want, and you’re doing him more of a favor by giving him the opportunity to be part of your pleasure than keeping him out of it “for his own sake.” If he can’t handle all this, then he’s not going to be much fun anyway. Good luck!
The Joe
From LD Grant:
This is all your fault, but it's not unfixable.
First, why would you get intimate with (AKA bang) this guy without feeling comfortable enough to get yourself off, even if by hand or whatever battery-powered plastic delight? We can keep asking why you've done this, but it doesn't really matter. Now you want to fix it.
DO NOT TELL HIM. Instead, re-train him. Most guys are pretty Pavlovian—so get him used to the ringing of another bell. If the guys sucks at pleasing you but you want to stay with him, the easiest way to guarantee your orgasms is to introduce touching yourself (or him getting more hands-on) by treating it as a kink of sorts... a pervy game that will enable you to get what you want and make it feel more exciting and new to him without insulting his skills. It will go over so much easier than any type of heart-to-heart you think you could pull off. (Believe me, no matter how delicately you think you word it, any guy is going to feel seriously dejected if he learns he hasn't been getting you off.)
Now I don't know your guy, so you may have to tweak the details of the exact how. If you vacation, introduce touching yourself as a naughty, trying-something-new away from home. (By the way, fancy undies always help with vacation sex. In general, fancy, or at least matching, undies make almost any situation better.)
Or, if you get a little sauced from time to time, pretend to get a little too sauced. You can blame the drink, get a little raunchy, and take care of yourself while you're going at it. Then, the next day, stroke his ego by telling him the only thing you really remember about the night before is how unbelievable the sex was. Then you can ease into it (pun intended) as a normal thing.
But go easy. Pull out a foot-long vibromatic, and he's gonna think his goods are not good enough. Use the hands first, and gauge his reaction and how open he may be to equipment in the bedroom... not that the bedroom should be the only room. In fact, it may be part of the “kink” to try something new outside of the bedroom, or the norm.
Now, your worst-case scenario...
Most guys love normal. Guys like to be right in the head, right in the bed. If you tell him, it's gonna be like admitting to cheating on him, because you did—you cheated with an idealized him. That's going to mess with his head and consequently what goes on in your bed in the future. Tell him now, and he might never be able to satisfy you. If he finds out, he most likely will freak out and act out—doing anything from breaking up, to giving you the cold shoulder, to thinking he has something to prove and cheating.
It's also grade-A bitch material to unleash this info during a fight or break-up. Try to be adult and not continue the cycle of guys are assholes and women are bitches. The truth is: All people can end up being rotten to one another. And if you purposefully damage someone and send them out into the world, you are creating a bigger bastard and unleashing it on the next woman to land him.
And it sounds like you DON’T want that if you're willing to stick with some guy who can't even make you come.