Dear Em & Lo: Help, I Can't Orgasm with My Boyfriend!


photo by Brandon Baunach

Dear Em & Lo,

I’ve been dating my boyfriend for five months and we have a great relationship…well, almost great. When we have sex, I have a hard time crossing the finish line. We’ve tried many positions and everything feels great. I just can’t orgasm. It’s at the point that it’s getting really frustrating for me, and any help would be greatly appreciated!

— Desperate for a Victory Lap


If you want to know how you and your boyfriend can orgasm simultaneously during penetration every time, sorry, you’re out of luck. If we knew that, we’d be richer than Oprah. But here are ten things we do know that will help increase your chances of orgasmic success…

1. We’re assuming by “sex,” you mean penile penetration. And that’s your first mistake. You say you’ve tried many intercourse positions, but maybe it’s not an intercourse position that will ultimately do it for you — maybe it’s oral sex, or handwork, or some combination of the two. There’s no shame in getting your orgasm via non-intercourse means — the majority of women don’t. Nor is there any shame in you having your orgasm and then him having his. Remember, sex — especially for women — doesn’t necessarily happen in a straight line, i.e.  your orgasm won’t necessarily be located conveniently at his finish line, or vice versa. Plus, it’s much easier for gals to keep going after a Big O than the lads. And you may find that certain intercourse positions feel even better (perhaps even orgasmic) after you’ve had one orgasm.

2. Again, intercourse alone is orgasmic for very few women, given how far the clitoris is from the vaginal opening — and how key clitoral stimulation is for most women’s orgasms. So don’t forget to supplement all those positions with a little extra clitoral stimulation — your hand, his hand, a small vibrator, a helpful neighbor’s hand…

3. Three words: Coital Alignment Technique. Learn it, live it, love it, Google it. In fact, any position where your bodies are mashed up against each other is good — because close contact means more friction down there, and more friction down there means more clitoral stimulation.

4. Try a vibrating love ring, like this one from GoodVibes. Because vibrating clitoral stimulation could be just the thing your intercourse life has been missing. You know all those times a dude looks at a sex toy and thinks, “Hey, my penis doesn’t vibrate like that?” Well, now it can!

5. We’re assuming that you can orgasm on your own, in which case, have you tried playing a little show-and-tell and teaching your boyfriend how to mimic that?

6. If you can’t orgasm on your own, then scratch everything else we’ve said and start masturbating! Often! Treat yourself to a vibrator, dim the lights, think some sexy thoughts and let the love flow. Because in our ten years of dishing sex advice, most women we’ve spoken to find it easier to learn solo first.

7. Sex toys are your friend. If your boyfriend is the jealous type, remind him that sex toys don’t cuddle and they’re useless at pillow talk. In addition to vibrating love rings, there are tons of other great toys for couples, like finger toys (which can really turn hand work up to eleven) and small pebble-like vibrators, which can nestle comfortably between your bodies.

8. Have you lubed today? Remember, man-made lube is not a crutch and using it doesn’t mean you’re not that into the sex. In fact, lube is one of the greatest bedside accessories we know. Using lube means that your sensitive parts are less likely to get over-sensitive while you’re trying out various different hand, tongue, toy, and intercourse techniques. And you’ll avoid rug burn!

9. Try not to over-think your orgasm. It sounds impossible, we know, but the more you stress about your happy ending, the less likely it is to happen. Sure, keep experimenting, and try out everything we’ve suggested here — but try not to think about this as a mission to O. Rather, it’s a mission to improve your sex life. Because orgasms are kind of like bad boys — the more you ignore them, the more likely they are to show up.

10. Finally, be patient. Five months may feel like forever to you, but in the grand orgasmic scheme you’re really only just getting going. Just because your orgasm hasn’t made an appearance yet in this relationship, doesn’t mean it won’t. Orgasms are mysterious things and sometimes things just click into place one day. Hey, long-term monogamy has got to have its benefits, otherwise we’d never enjoy the pleasure of board games.

We hate to sound like a self-help book (what color is your parachute, anyway?) but when it comes to sex, the journey is meant to be at least half the fun. Of course every woman has the right to an orgasm with her boyfriend, and we understand your frustration, and you should definitely be demanding, but don’t forget to appreciate this great relationship and enjoy the nice-feeling sex you do have, because having a good time together is the best foundation for having an orgasmic time together.

Gooooooooooo sex!

Em & Lo


  1. @0329 your first mistake is making your pleasure about your boyfriend’s happiness and ego instead of YOUR pleasure. If you don’t orgasm every time you have sex, there is nothing wrong with that. You’re in the vast majority. I masturbate on average 4-6 times a week and even I (when I’m actually dating someone) don’t orgasm every time. sometimes the sex is rushed due to busy schedules. Sometimes we don’t have time for adequate foreplay.

    You dont mention how old your boyfriend is, but it sounds like he is in his early to mid 20s. The fact that he is more concerned about his own bruised ego instead of extending the foreplay with you and working to find what YOU like so you can climax, that is a dead giveaway. And I think it is beyond, beyond shitty and disrespectful that he has dared to tell you that you’re the “only” woman he has had trouble bringing to orgasm. I call bullshit. Either he has dated some decent orgasm fakers, or super-orgasmic porn star wannabes, or he has no idea what a woman’s orgasm looks and feels like. He is saying it to make you feel bad and that is incredibly immature.

    Your body might need more stimulation or a certain type of stimulation for you to climax, especially if you’re on medication that decreases your libido. Tell your boyfriend that instead of making you feel bad or dragging his ex’s into the situation, to work with you and put time into exploring your body and HELPING you achieve orgasm. If not, then kick him to the curb honey. Life is too fucking short to waste on some dude who makes you feel bad about how your body responds to what he is and isn’t doing. Plenty of men would love the opportunity to make sex fun again and help you come

  2. Hello, im having trouble having an orgasm with my bf. I am on medication (welbutrin 300 mg, and zoloft 25 mg). Could that be causing my problem? I mean I’ll use toys for hours and nothing happens. Sometimes i’ll get very wet but other times i just dry up. Sex is pretty new to me. I became active at 27, im currently going on 29. I don’t know what it is. I came alot one time, he used a cucumber on me and i came for the first time, I wasn’t on my medication though.

    He expects this to happen all the time now with intercourse. I mean, is my vagina used to the cucumber and im not being pleasured enough by my bf? It feels good when we’re having sex, but his goal every time is to make me orgasm. He gets frustrated and doesn’t feel like he’s good enough. I love having sex with him, but he is just makes me feel like i HAVE to orgasm every time, he gets upset when i don’t. Its just so much pressure, plus i have a hard time trying to concentrate on my own.

    I don’t know what to do! Sometimes he doesn’t want to have sex with me because he can’t make it happen. I am not his first, he’s had many women before me and apparently im the only one he’s had trouble accomplishing this with. I’m pretty fed up with it. I don’t want this to be the reason we have sex. What should i do? What can i do? I mean im sp fed up i don’t even have the patience to concentrate while im trying to masturbate myself. He’s even starting to make me feel like it’s something i have to do.

    Before i was with my bf i thought masturbation was wrong, and i wasn’t interested in it. Truthfully im not really into it now. I feel stupid when i do it. Is there any hope for me? I just want to feel good and make my bf happy. What should i do?

  3. Pingback: Sugasm #157
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  5. lucky me–i could never reach orgasm during intercourse, until one certain boyfriend showed me that it was easier for a woman to reach orgasm when she was on top…so she could adjust pressure, friction, angle and speed…and merciful heavens, he was right! then, once you’ve reached orgasm that way, it’s easier to explore other ways. i will always be grateful to this man for his caring and understanding.

  6. Practice Practice Practice! The more the better! Women need much more mental stimulation than guys do… find what really turns you on before you even get touchy feely.

  7. Thanks for the advice! You both made some very good points and I will do a little bit more “research” of my own~~

    I love your new site by the way!

  8. Great advice ladies! I had never heard about the Coital Alignment Technique — I think it’s the key to unlocking my Big O.

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